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Raj
Hey, it's Raj and Noah, and we're back with a new season of Am I Doing It Wrong? The show that explores the all too human anxieties we have about trying to get our lives right.
Noah
Because we're still doing a lot of stuff wrong.
Raj
But who isn't? That's why each week we're talking about the topics that we could all use a little helping hit with. Whether it's making new friends as an adult, managing our emotions, or even dreaming.
Noah
We'Ll be talking to experts in their fields who are definitely doing things right, so the rest of us can be a bit wiser and a lot better equipped to handle whatever life throws at us.
Raj
Subscribe now and listen to new episodes of Am I Doing It Wrong? Dropping every Thursday starting January 1st, wherever you get your podcasts.
Noah
And for the first time ever, we're gonna have full video episodes on YouTube. Because as long as there are things to get wrong, we're gonna be right here to help you do them better.
Don Wildman
Love y'.
Professor Cecily Zander
All.
Jacob Goldstein
Odoo, this is Jacob Goldstein from what's yous Problem? When you buy business software from lots of vendors, the costs add up and it gets complicated and confusing. Odoo solves this. It's a single company that sells a suite of enterprise apps that handles everything from accounting to inventory to sales. Odoo is all connected on a single platform in a simple and affordable way. You can save money without missing out on the features you need. Check out odoo@o d o o dot com. That's o d o o dot com.
Raj
Lunch was great, but this traffic is awful.
Patient
Can we stop at a bathroom?
Professor Cecily Zander
Are you all right?
Patient
I keep having stomach issues after eating, like diarrhea, gas and bloating, abdominal pain, and sometimes oily stools. Sound familiar? Those stomach issues may actually be a pancreas issue called exocrine pancreatic insufficiency, or epi. Creon. Pancrelipase may help manage epi. Creon is a prescription medicine used to treat people who can't digest food normally because their pancreas doesn't make enough enzymes.
Creon Advertisement Voice
Creon may increase your chance of fibrosing colonopathy, a rare bowel disorder. Tell your doctor if you have a history of intestinal blockage or scarring or thickening of your bowel wall. If you are allergic to pork, or if you have gout, kidney problems, or worsening of painful swollen joints, Call your doctor if you have any unusual or severe gastrointestinal symptoms or allergic reactions. Take Creon as direct by your doctor and always with food. Do not chew capsules, as this may cause mouth irritation. Other side effects may include blood sugar changes, gas, dizziness, sore throat and cough. These are not all the side effects of Creon. Call 8639110 or visit creoninfo.com to learn more. That's C R-N info.com I'm asking my.
Patient
Doctor about epi and if Creon could help.
Don Wildman
It's 2am on a March morning in 1847 during the Mexican American War. Under a canvas canopy somewhere in the countryside, a US army captain sleeps fitfully. Around him in their own tents, his troops snore and breathe and mutter in their dreams. Out on the camp's perimeter, the night watch whispers to each other. There's all the normal sounds of night crickets, cicadas, frogs. An owl hoots in the trees. And then there's that hissing under the captain's cot. He bolts upright, dives into the night a split second before a 12 pound artillery shell detonates, shredding his tent with shrapnel. Enemy attack? Hardly. In fact, one of his own men had planted the explosive with intention to harm if not kill. How awful do you have to be at leading men for one of your own to try and murder you? And how does such a dreadful officer live to lead another day, only to be finally named general? Hey, it's American history hit. Thanks for listening. I'm Don Wildman. Across the span of America's wars in which so many citizen soldiers have courageously fought and died, the leaders of those wars, the generals, are so often brilliant at executing strategy, supply and even political maneuvers. Today's episode isn't about them. Instead, it's about the blunderers, the overreachers, the outmatched and outsmarted, the disastrous decision makers who put their forces and their nation into harm's way with what proved to be, well, general ineptitude. Who were America's worst generals? Today we look at a few outstanding examples of those who, if history is our guide, had no business calling the shots and will proudly do it with a returning voice in such matters. Professor Cecily Zander of the University of Wyoming, author of a new book just out there on the horizon, entitled Abraham Lincoln and the American west, coming out at the end of this summer, as well as Army Under Anti Militarism in the Civil War. She is an expert in Civil War history who has joined us for a number of previous episodes about U.S. grant as well as others. Welcome back. Cecily Zander Ready to dive into the inglorious leaders we'd rather forget.
Professor Cecily Zander
Hey, Don, it's great to be back. Unfortunately, I think I've spent most of my career studying these guys and not the good ones. So I'm. Yeah, I'm absolutely ready.
Don Wildman
Yes, they always get the attention. We got a list of six. There could likely be more. But if a great general is, in the broad sense, one who sees the field, the tactics of forces, the terrain, the time of battle, who makes the decisions of clarity and conviction, ours today, as I mentioned, did not. So what qualifies a bad general in general?
Professor Cecily Zander
It's a great question. I would sort of put maybe sort of two related issues forward. Things that tend to hold back military officers. I think one is inability to put ego aside. I think we're going to talk about a lot of guys who had really big egos and thought they knew best and in a related fashion, didn't feel the need to consult anyone else or to get along with anyone else. And I think something that makes a great general is the ability to get along with superiors and subordinates. And we have a list of guys today who really failed to do that and often, sometimes even actively tried to undermine their superiors and in so doing undermined the national war effort.
Don Wildman
Sure. And they lack tactical ability would be, I think, another. And they can be. I don't know if downright coward applies. Yeah, as someone who never served, I'm fearful to call anybody that. But anyway, let's start with Braxton Bragg, a name for the books if ever there was. He was a Confederate general in the army of Tennessee, possibly the most hated general on our list. Why?
Professor Cecily Zander
So Braxton Berg had a lot of problems, not least of all his single eyebrow, which I think, you know, has sort of, you know. And again, I encourage our listeners to just Google and admire. I mean, he truly looks like a Muppet more than a human being. But, you know, Braxtonbreg, he didn't have a lot going for him. He was. While he was a West Point graduate and had a good deal of military experience coming into the war, he was someone who, in a sort of typical 19th century fashion, suffered from a variety of ailments. I don't think he ever felt very well in his life. I don't think he ever woke up and sprang out of bed. He sort of woke up and longed for the invention of ibuprofen. I mean, he had aches and pains and all this turmoil, but he also had a personality that just made him absolutely impossible to get along with. There was a famous story in the old army, and it shows up in memoirs, people like Porter Alexander, Ulysses S. Grant, where Bragg, for some reason, was doing several administrative roles at an army post in the American West. He was both the quartermaster and acting commander of the post. And he made a requisition as quartermaster for some supplies. And he sort of supposedly moved the paper over to the desk across the room, his post commander desk, and denied the request and said it had been improperly filed and sent it back. And then he moved back across the room and he sat down at the quartermaster desk and wrote this explanation of why it had been properly done and then sent it back to the post commander, who was him. And then, you know, they sent it back all the way up to the kind of chief of the region for the army. And he said, My God, Mr. Bragg, you've quarreled with every man in this army and now you're quarreling with yourself. And that, I think, is the quintessence of Bragg's failure. He could not get along with another human being. He could. He could hardly get along with his own mind.
Don Wildman
There you go. He had a fort named for him. I mean, Fort Bragg. But then.
Professor Cecily Zander
Yeah, and that. That tells you the sort of paucity. So the kind of general plan there in the First World War was name forts after the most famous American soldier from that state. Bragg was a North Carolinian. And there were. There were simply no others, I suppose, who they could have chosen.
Don Wildman
But then they renamed the fort anyway. Now it's called Fort Liberty.
Professor Cecily Zander
Yeah.
Don Wildman
As of 2023, he was the merciless tyrant. Uncanny ability to turn minor wins and losses into strategic defeats. Yeah, that was cited by his subordinates that he worked for or one in particular, Sam Watkins. So interesting. No tactical talent, I suppose.
Professor Cecily Zander
No, not really. He was someone who would sort of fixate on all the bad things that were going to happen. You know, he would kind of spool out this scenario where if he did this, well, that was going to be disastrous, so he should do this, but that could also be disastrous. And he sort of immobilized himself and his men sort of rarely knew what they were supposed to be doing. And then he would. He would tend to place blame for the failure of a campaign or a battle on whichever subordinate had happened to sort of rub him the wrong way. Most recently.
Don Wildman
I see.
Professor Cecily Zander
And that's not something that commanding generals are supposed to do.
Don Wildman
His attempted invasion of Kentucky, 1862, stands out. It was his first campaign as a general and he had this to say to the people of the state, Kentuckians, I have entered your state with the Confederate army of the west and offer you an opportunity to free yourselves from the tyranny of a despotic ruler. Then what happened?
Professor Cecily Zander
Well, he spends about six weeks sort of bumbling around central Kentucky. He's facing a Union army under the command of Don Carlos Buell. Not a name that rings through history, but one that I think haunted Braxton Bragg. He kind of maneuvers, he fights a couple of battles against Buell, and then he gets himself into a fight that takes place at the end of the year, sort of 1862, over Christmas, and into New Year's, in which he potentially sort of fights to a tactical stalemate. Again, Buell's not a great military genius, but he's so worried about what Buell has in reserve. He's imagining Buell has this sort of massive, great army to bring to bear. He sort of skedaddles from Kentucky, abandons something like 10,000 rifles he had brought with him because he expected the people of Kentucky to sort of flock to the Confederate banner and sort of begin to march with his army. And he. He essentially abandons Kentucky for the remainder of the war. For the Confederacy, that's a problem because we have evidence of both Lincoln and Davis saying that really Kentucky is the key. I mean, Lincoln says multiple times, to lose Kentucky is to lose the whole thing. You know, Lincoln says, I have to have Kentucky on my side. Any real Confederate occupation of Kentucky is a threat to the Union war effort. And Bragg gives it up after about six weeks.
Don Wildman
He's called an insufferable piece of nonsense by the local paper, the Louisville Courier, and gives it all up. And then from that moment on, Kentucky is a border state on the Union.
Professor Cecily Zander
Side, and Bragg begins sort of a very swift retreat on the back of that through Tennessee. And Tennessee is a Confederate state, and Bragg is the reason the Confederacy loses sort of that bounty as well. I mean, Tennessee is just as important in terms of its rivers, its geography, and its potential bounty for supplying the Confederate war effort.
Don Wildman
He did win the battle of Chickamauga. Northern Georgia. Was this his only win?
Professor Cecily Zander
It's his only win. So it's an easy list to remember for trivia if you're, you know, out at the pub. But even then, it was more a failure of the Union commander, William Rosecrans, who we're not going to talk about, though we certainly could. William Rosecrans, inexplicably, in the middle of the battle of Chickamauga, pulls a regiment of about A thousand men out of the center of his line and moves them to a flank that he thinks is under threat. It's a miscommunicated order. It's a problem. But you can't pull the center of your army out of place and expect to win a battle. James Longstreet, who has been recently transferred to Bragg's army because he'd been having a tip with Robert E. Lee, happens the show up at that exact moment. He crashes through the line. The Confederates win a victory, but they don't follow up because Bragg has kind of no wherewithal to continue to punch at the United States.
Don Wildman
This is the case with several of these guys. They are guilty of not pursuing the troops that they have either stunned or defeated for the time being. We're going to talk about a big example of this in a moment. This seems to be a common trait.
Professor Cecily Zander
Yeah. And then Bragg is occupying what's called missionary heights. And if you've ever been to Chickamauga, Chattanooga, or, you know, you can just look at a picture, these are massive sort of cliffs, ridges that are very common in this sort of part of Appalachian Georgia. They're almost impossible positions to lose. Bragg has several hundred feet of elevation over his enemies and Ulysses S. Grant shows up and in a matter of days has stormed the heights, kicked the Confederates off, and they're out of Tennessee for the rest of the war and soon to be out of Georgia. I mean, it's amazing that even in the best, most defensible position that perhaps any Confederate army had during the war, Bragg still managed to concoct a defeat.
Don Wildman
There are so many notes on my page about things that he is known to have done that were just so despicable. Sending a soldier to ride into enemy fire, to collect harnesses off of dead horses, questionable idea. One soldier actually tried to kill him. A 12 pound shell under his cot. Bragg uninjured, remarkably.
Professor Cecily Zander
Yeah.
Don Wildman
He orders the execution of a 19 year old for going home to his, to his mother because of desertion, which I suppose is understandable, but many appeals by other generals he ignored. This is a way to really disrespect your troops, isn't it?
Professor Cecily Zander
Yeah. And again, sort of we talked about in another episode. These are citizen soldiers. They aren't professionals. Bragg is a professional soldier. He's a West Point trained officer. He understands military order and discipline, but he doesn't understand that the men under his command do not share those sentiments and do not share that desire for proper order. And he tries to enforce it and it makes him a Tyrant to his soldiers. He does not have their love.
Don Wildman
Most of these guys distinguish themselves, as you said before, with large egos. That certainly applies to our next worse. I really want to talk about this guy. General George McClellan, for a time, the commander of the army of the Potomac, the major commander under Lincoln at the beginning of the war. Caveat on McClellan. His fatal flaw seems to be over preparation. He was much respected and even a military prodigy at West Point. His skill was in building and training an army much loved by his troops. The opposite of a brag. Loathed by Lincoln in the end. But you wonder where it came from, whether it was cowardice, which people tend to think of, or whether he was just a kind of too compulsive about his army preparations.
Professor Cecily Zander
Yeah, he was really great at imagining these bugbears that existed. And he could come up with a whole host of reasons in any given battle to not do something, to not take action. He has 30,000 troops in reserve. So I can't attack, or, you know, my men are too fatigued. I can't follow up. He was very good at sort of making excuses for why he wasn't going to move forward.
Don Wildman
Where did we see this take place?
Professor Cecily Zander
We certainly see it after the battle of Antietam. The Battle of Antietam is sort of a microcosm of George McClellan's anxieties and also his failures as an army officer. Not least because in the lead up to the battle, Robert E. Lee chooses to invade Maryland. He decides to sort of pull his men, his Confederate army, out of Virginia to give some relief to the Shenandoah Valley, to the Virginia planters, to the people of the state. So he moves into Maryland. McClellan is placed back in command of the army of the Potomac. He is supposed to follow Lee. He does so quite slowly. Lincoln was fond of saying, he once commented of McClellan, Sort of pacing decisions. He has a case of the slows. He was never in a hurry to get anywhere. He kind of slowly follows Lee. The one advantage to this is a bunch of his cavalry, which are the eyes and ears of a Civil War army, stumble upon Lee's camp. Camp that had been recently abandoned by Lee and his high command, they discover, rolled around the butt of a cigar, the entire plan for Lee's operation and the battle that was to follow. So George McClellan knows exactly what Robert E. Lee is going to do. He doesn't for once have to imagine Lee's plan. He actually knows it. And he still fails to bring the battle to any kind of Great, substantial victory. After the end of the day of fighting on September 17, 1862, yes, McClellan's army occupies the battlefield, but the next day, he decides not to pursue lee, not to pursue a very wounded confederate army. He lets lee escape across the river. Abraham lincoln is telegraphing him, saying, what's going on? He says, the horses are tired. We can't really move. We can't do anything. Lincoln is saying, what made the horses so tired? He simply doesn't understand. He's trying mcclellan to push mcclellan to move. But even with his enemy's battle plans and enough of an occupation of the battlefield to consider himself having won a victory, he doesn't follow up. He fails to pursue lee. He lets the great confederate commander get away.
Don Wildman
Yeah, I mean, it's so commonly talked about in the early days of the civil war, People thought it was going to be such a short war, but it's kind of a chicken and the egg thing. How much did mcclellan have to do with that mindset?
Professor Cecily Zander
It's really important to understand kind of where mcclellan is coming from here. He's only 35 years old when he's placed in command of the most important union army. I mean, it's pretty remarkable, his rise through the ranks. He'd been, again, a west point graduate. He'd had experience in mexico. Like many of these officers, he had gotten out of the army and into civil life. He'd tried to make his fortune in the railroads. But he comes back. He knows he's going to be really important. He sort of cajoles, kind of pushes his way into a command, and he emerges really quickly as this quite soldierly looking fellow, A guy that other military commanders really respect and appreciate and someone lincoln is willing to take a chance on. The thing about george mcclellan is he's a conservative and also, as we will find out over the course of the war, a capital d, democrat. So in opposition to the leading republican party, which lincoln represents, which sort of wanted a very aggressive, sharp war against the confederacy, they really, truly wanted to compel the confederates back. Mcclellan's strategy is one of, I think, lowercase conservatism. Let's not fight them too hard. Let's give them a chance to sort of realize the error of their ways. And if we don't punish them too harshly, if we hold back, although we have superior resources, we have more men in every category, we outmatch them, they'll come back. It'll be easier to reunify the country. So I'm going To fight a very slow, very methodical, very conservative war that's not going to produce the victories that the United States needs. And when, by the time of the seven days battles and then Antietam, McClellan is pitted against Robert e. Lee, one of the most aggressive generals in American history, he has no hope of achieving any kind of substantial victory.
Don Wildman
It's almost like he was a victim of his own logistical intelligence, wasn't he? You know, where. Where you think so hard about what's going to happen and the results of your actions, the consequences of your actions, that you end up hamstringing yourself and not taking action. And that's kind of his flaw. That being said, you know, he's not an entirely bad man. You know, like I have always thought of that before. I started reading a lot more for this, and I realized that it might just be a curse, you know, that this guy just thinks too hard about things. And he is a bit of a coward, I think, but above coward. I believe he's maneuvering for the future at all times. And within himself, he sees a future for himself because he does have a big ego, and he probably sees himself as president at some point.
Professor Cecily Zander
Yeah. I mean, if you read the letters that he wrote to his wife, who I am always delighted to inform students, was named Ellen McClellan. I mean, it is amazing the way he sort of describes his achievements. You know, after. After a battle, he writes to her that it was a masterpiece of art. I mean, he just. He genuinely thinks of himself in these kind of grandiose ways. And fortunately for us as historians, his wife received all these letters, I assume, read them, sort of shook her head, rolled her eyes, and then put them in a box. And then after he died, she published them so that we could all suffer with her.
Don Wildman
Oh, my God. That's funny. He was called little Mac by his soldiers. Let's talk about the battle of the seven pines. Union casualties had exceeded 5,000 on May 31 and June 1 of 1862. McClellan's whole role in the civil war was really the early days of this. Before he gets sacked by Lincoln and he writes to his wife. One of those letters. I am tired of the sickening sight of the battlefield with its mangled corpses and poor suffering wounded. Victory has no charms for me when purchased at such cost. I can imagine myself writing that. Not quite those word choices, but, you know, there's a human being here. We can't fault him for that.
Professor Cecily Zander
Yeah, and I think, you know, that was still. Again, it's an important point. About this being the early days of the war, they didn't yet have a sense that, that those were, I mean, truly small numbers compared to the casualties that would come later. And, you know, one of the chief criticisms that's leveled at Ulysses Grant after the war was that he was a butcher, that he sacrificed men unnecessarily. I think if McClellan had. Had ever been labeled a butcher, it would have crushed him. But just to sort of offer some contrast to listeners, when. When Grant undertakes his initial attacks at Cold harbor at the very end of the Overland campaign, there's about 7,000 casualties in 20 minutes of an assault on the first morning of that day's fighting. And so those numbers within a couple of years are going to change quite drastically. Frant is crushed by what he caused at Cold harbor, but they were casualties by that point in the war that both sides were sort of willing to sustain early on. When McClellan is talking during the Peninsula campaign, those are numbers that are still really, really shocking to, to both military officers and the American people.
Don Wildman
McClellan, a mixed bag of bad, gifted military man, lacked vision in so many ways. And this was clouded by his disparaging view of leaders above him. And he had no pluck. I mean, let's just say it. He was a. He was a Napoleonic military leader who could see all that going on, but he was not willing to take those chances. Okay, two down. Way down. When we come back, we'll move back in time to the most revolting generals of the revolution. First, let's hear from the sponsors.
Jacob Goldstein
This is Jacob Goldstein from what's yous Problem? When you buy business software from lots of vendors, the costs add up and it gets complicated and confusing. Odoo solves this. It's a single company that sells a suite of enterprise apps that handles everything from accounting to inventory to sales. Odoo is all connected on a single platform in a simple and affordable way. You can save money without missing out on the features you need. Check out Odoo at O D O o dot com. That's O D O o dot com. This is Jacob Goldstein from what's yous Problem? Business software is expensive. And when you buy software from lots of different companies, it's not only expensive, it gets confusing. Slow to use, hard to integrate. Odoo solves that because all Odoo software is connected on a single affordable platform. Save money without missing out on the features you need. Odoo has no hidden costs and no limit on features or data. Odoo has over 60 apps available for any needs your business might have, all at no additional charge. Everything from websites to sales to inventory to accounting, all linked and talking to each other. Check out odoo at o D O o dot com. That's O D o o dot com.
Raj
Hey, it's Raj and Noah and we're back with a new season of Am I Doing It Wrong? The show that explores the all too human anxieties we have about trying to get our lives right.
Noah
Because we're still doing a lot of stuff wrong.
Raj
But who isn't? That's why each week we're talking about the topics that we could all use a little helping hit with. Whether it's making new friends as an adult, managing our emotions, or even dreaming.
Noah
We'Ll be talking to experts in their fields who are definitely doing things right so the rest of us can be a bit wiser and a lot better equipped to handle whatever life throws at us.
Raj
Subscribe now and listen to new episodes of Am I Doing It Wrong? Dropping every Thursday starting January 1st, wherever you get your podcasts.
Noah
And for the first time ever, we're gonna have full video episodes on YouTube because as long as there are things to get wrong, we're gonna be right here to help you do em better.
Professor Cecily Zander
Love y'. All.
Raj
Lunch was great, but this traffic is awful.
Patient
Um, can we stop at a bathroom?
Professor Cecily Zander
Are you alright?
Patient
I keep having stomach issues after eating, like diarrhea, gas and bloating, abdominal pain, and sometimes oily stools. Sound familiar? Those stomach issues may actually be a pancreas issue called Exocrine Pancreatic insufficiency, or epi. Creon may help manage epi. Creon is a prescription medicine used to treat people who can't digest food normally because their pancreas doesn't make enough enzymes.
Creon Advertisement Voice
Creon may increase your chance of fibrosing colonopathy, a rare bowel disorder. Tell your doctor if you have a history of intestinal blockage or scarring or thickening of your bowel wall, if you are allergic to pork, or if you have gout, kidney problems or worsening of painful swollen joints. Call your doctor if you have any unusual or severe gastrointestinal symptoms or allergic reactions. Take Creon as directed by your doctor and always with food. Do not chew capsules as this may cause mouth irritation. Other side effects may include blood sugar changes, gas, dizziness, sore throat and cough. These are not all the side effects of Creon. Call 800-633-9110 or visit creoninfo.com to learn more. That's C-E O N info dot com.
Patient
I'm asking my doctor about epi and if Creon could help.
Don Wildman
Okay, we're back with Professor Cecily Zander marching through our worst generals of history, at least the American variety. A few descriptors of our next guy here. Mercurial, eccentric, contentious, arrogant, disobedient, conspiratorial. This guy they made a major general in the Continental army, the one, the only General Charles Lee. Okay, insubordination. Let's start there.
Professor Cecily Zander
Yeah. I mean, when you think from the very beginning that you should have been the guy they put in charge and they pick somebody named George Washington, you're going to have a problem and you're going to spend the rest of the revolution trying to convince anyone you can possibly get the ear of that they made the wrong choice.
Don Wildman
Why did he think he was so good?
Professor Cecily Zander
He had more experience. I think, genuinely coming into the American Revolution. You wouldn't have found a soldier willing to fight for the American side with more sort of genuine battlefield experience than Charles Lee. And he, unlike George Washington, hadn't been a sort of disaster in his first few outings as a military leader. I mean, Washington and the Indian wars, that is not a record that you want to run on if you want to be the general of the Continental Army. Charles Lee, extremely successful fighting for the British in the Seven Years War. He had also gone and fought for the Polish army during some of the sort of European wars at the end of the 18th century. And he comes back to the United States. He's a really powerful figure. He has a ton of military experience. He has important friends. He has pedigree. And he thinks that the Continental army would be correct or the Continental Congress would be correct in choosing him to be the leader of the Continental Army.
Don Wildman
And they don't, because they can see what the truth or not or just Washington's the more sensible choice, I guess.
Professor Cecily Zander
I think. Yeah. I think Washington is just better known to them.
Don Wildman
Sure. Yeah. Very soon in this war, 1776, he is captured by the British, Very embarrassing situation. And he's kept prisoner, or at least away from the field of battle for two years. Right?
Professor Cecily Zander
Yeah, yeah. In the sort of New York campaign, he's sort of taken prisoner. He's writing to Washington, he's writing to sort of important congressional leaders saying, can you help get me out? Can we get some kind of prisoner exchange going? And they just kind of ignore him, which I think he takes as a real slight, like, they think so little of me that they're not Even going to help me get out, I could be helping the war effort. And he shows this propensity in the capture, in the moment he is captured. He's not very good at retreating. And sometimes as a general you need that skill. And in the American Revolution, funny enough, I think the greatest skill George Washington had was getting his army out of scrapes. Washington didn't actually win a lot of battles, but he didn't sacrifice his army. He didn't conduct disorderly retreats. Charles Lee had shown a propensity to do that in his capture in the New York campaign. And it's going to be his ultimate downfall when he does finally get exchanged and return to the battlefield to serve under Washington.
Don Wildman
You know, that couple of years later I mentioned conspiratorial. I mean, it is speculated that while he was, after he'd been captured that at some point he gave away plans as to how to, you know, approach defeating the Americans.
Professor Cecily Zander
Yeah, he, he sort of. Right. You're sort of sitting around for two years with your enemy. And he had been born a British citizen, he had fought for the British army, he'd fought alongside some of these guys, you know, shooting the, you know, breeze. And, and I think he probably, whether he intended to or not, you know, did expose some of the principal parts of the American war effort though, you know, to be honest, I don't know that the British needed that much information. It was pretty clear what the Americans were trying to do. The Americans didn't have all that many options in terms of the strategy that they were going to pursue. But any information is good information in a war.
Don Wildman
Well, you don't have many leaders to choose from of that level with that kind of experience, so it's understandable. But he really does shame himself with the Battle of Monmouth. Let's explain why. 1778.
Professor Cecily Zander
Yeah. And he is sort of back as a really sort of right hand guy to Washington. He's been given a pretty substantial role in this campaign. He's supposed to be leading the vanguard of the Continental Army. He's supposed to be the person who really pushes through, kind of penetrates to lead the way for Washington and the rest of the army to kind of overawe the British. And you know, at Monmouth, he gets up there and he has explicit orders from Washington to attack early in the morning, as soon as possible. And Washington does not write bad orders. This is not unclear. There is nothing unclear about the directive that Charles Lee has gotten to initiate the American attack on the British troops. Yes, Lee delays, he ignores the order and when he finally does get around to the attack, he believes that he has fewer men. He doesn't really fully commit his troops. This is going to be where an accusation of cowardice comes from. You don't fully commit your men. And then the retreat that he conducts in the aftermath is absolutely disastrous. I mean, the militia, they come running back, they're sort of tripping over themselves. They're. They're looking for cover. I mean, it just looks unsoldierly, it looks unmilitary. And Lee is sort of deemed the cause of all of this failure. He had disobeyed orders, he hadn't followed what Washington had told him to do, and he hadn't kept his men safe or let Washington know he was retreating. Washington, at the same time as Lee's troops are streaming away from the battlefield, is still trying to maneuver his men into place. Assuming Lee had done his job. So he also puts the remainder of the army at risk.
Don Wildman
Exactly. Ignominiously. He shows up in, in Hamilton, in the musical Hamilton with having shit the bed at the Battle of Bournemouth. That's the line. There was a moment when he actually shouts at George Washington and everybody sees this. And that's the insubordination I talked about. He's convicted by court martial on disobedience of orders. He's basically, you know, seen to be shouting with. It's not a good look. I mean, this guy goes down with a very dishonorable reputation at the end of all this. Where's he end up in life, Charles Lee?
Professor Cecily Zander
He sort of. He has a property in Virginia. He goes there. He was probably someone who believed that, that this war was a springboard to a great political career, perhaps, you know, success in life. He raises horses, raises some dogs. He loved dogs. Which, you know, I think personally is a great quality.
Don Wildman
Yeah.
Professor Cecily Zander
Everything else aside, but he had sort of had chronic again, gout illness, disease, and we think that probably tuberculosis ultimately is what he succumbed to. Dies in deep debt and without much of a reputation at all. It's funny, we. American military history. There is one Lee that is among the great names and then one Lee among the worst.
Don Wildman
Were they. They weren't related in any way down the road?
Professor Cecily Zander
No, no, not the same. Lee's.
Don Wildman
Well, the takeaway from Lee is don't shout at your boss.
Professor Cecily Zander
Certainly not if he's George Washington.
Don Wildman
There you go. General Horatio Gates, Continental general, Revolutionary War again. Fought in the most pivotal battles. I mean, Saratoga, for goodness sakes, may have overstated his own role in that victory, but was you know, there was. He was far behind the lines. He then suffers catastrophic defeat at the Battle of Camden, 1780. His army collapsed. He fled when opposed by such a smaller force. What's the takeaway of Gates? You know, he's a mixed bag. Isn't he on this. On this kind of list?
Professor Cecily Zander
Yeah. And I think again, we see someone. You know, I talk to students a lot about sort of knowing your skill set, especially in classes on leadership and military history. Gates was an incredible administrator and organizer. And if he had been kept in that role within the Continental army, then I think he would be remembered among the great generals of the Revolutionary War. But because, as you just said, they lacked great battlefield commanders. They had to use everybody they possibly had. And Gates was not, despite his own assessment of Saratoga, a great battlefield commander. He forgot sort of basic information. And at Camden, what happened was that he concentrated the bulk of his troops attack against the British. Right. And he should have known because he had served in the British army and he knew something about tactics. He was a professional military officer. That's where the British army concentrated their strength. The strongest troops in the British line were always on the right side of the army. And that's where Camden sort of concentrates his ineffective, weak attack. He doesn't understand tactics. He doesn't understand how battlefield kind of events play out. He was a great administrator. He was a real aide to the Continental war effort. But on the battlefield, just a disaster.
Don Wildman
We're going to take a short break. When we come back, we have three more generals to go, and one of them's really bad.
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Raj
Hey, it's Raj and Noah. And we're back with a new season of Am I Doing It Wrong? The show that explores the all too human anxieties we have about trying to get lives right.
Noah
Because we're still doing a lot of stuff wrong.
Raj
But who isn't? That's why each week we're talking about the topics that we could all use a little helping hit with, whether it's making new friends, as an adult, managing our emotions or even dreaming, we'll be.
Noah
Talking to experts in their fields who are definitely doing things right, so the rest of us can be a bit wiser and a lot better equipped to handle whatever life throws at us.
Raj
Subscribe now and listen to new episodes of Am I Doing It Wrong? Dropping every Thursday starting January 1st, wherever you get your podcasts.
Noah
And for the first time ever, we're gonna have full video episodes on YouTube, because as long as there are things to get wrong, we're gonna be right here to help you do them better.
Professor Cecily Zander
Love y'. All.
Don Wildman
And we're back with Cecily Xander. We're addressing a list of the worst generals in U.S. history across all the wars. Cecily, before we get into this again, we have three more to talk about. It all gives one pause to reflect on the good generals. The Washingtons, the Grants, the Eisenhower. The role of a true general is a magnificent matter of wisdom and fire. No wonder there are so few great ones, right?
Professor Cecily Zander
Yeah, absolutely. And the ability, I think, which is almost sort of beyond most humans, to take responsibility for failures that aren't necessarily your fault. Yeah, yeah. Something that Grant and Washington and Eisenhower could do because they were the man at the top is say, if my men failed, I failed, and I'm not going to blame them. What we find with a lot of the guys we're talking about is they sought to place blame on others as often as possible. That is not the mark of a great leader.
Don Wildman
Yeah, I want to mention this guy. We don't have to talk at length, but William hull, War of 1812, tactically weak. I would file him under that. Surrendered the Fort Fort Detroit and his army to the British and Native American forces without even a fight after the initial invasion of Canada, August 1812. We don't hear enough about the War of 1812. That's why I want to mention this. The British had deceived him that they had larger forces. He feared for his own family inside the fort. The result of this is the loss of a Michigan territory which is magnificently huge. As a result, court martialed, sentenced to death, and then finally pardoned by President James Madison due to his service in the Revolutionary War. Was all this his fault? I mean, I just want to remember he fought bravely in those early years. Saratoga.
Professor Cecily Zander
I think he just sort of. For me, the story of William Hull is a guy who really understood what was going on. And he had urged the American government to do more to protect the Great Lakes and especially Michigan territory prior to the War of 1812. And he had written about how important these places were going to be, how they needed to be fortified and defended, and nobody listened to him. And I think when he wasn't heard, that's when he kind of gave up. And I think that was his failure. He had the right ideas, but he realized that was that all of his sort of commentary was falling on deaf ears. And he was unwilling to fight for a government that he didn't feel was going to back him up. I don't mean he was a coward. I don't mean he was a traitor. But I think it just ruined his enthusiasm, his willingness to fight. When he had all these really good ideas, and they simply weren't supported.
Don Wildman
All right, I want to know this guy. Just because the facial hair. Ambrose Burnside, Civil War general for the Union army, Known for his infamous failures and lack of tactical skill. Fought at the battle of Fredericksburg. Tell me about what was unique about his role in that battle.
Professor Cecily Zander
So he sort of demonstrates a stunning inability to learn from the failure of a tactical choice about seven times over. So the Battle of Fredericksburg is infamous in the American civil War. Fredericksburg, an interesting sort of town on the Rappahannock river in Virginia. Very quickly, from the bottom of the river, the town sort of scales these heights hills around the town. Robert E. Lee and the army of northern Virginia occupy the heights in and around Fredericksburg. They occupy most of the town. Ambrose Burnside has planned a rare winter campaign. This is a battle that happens in December. That's very rare for the American civil War. He needs to get his men across the river. The idea is to attack Lee, dislodge him from Fredericksburg off of these heights. The most famous ridge is called Marie's Heights. That's spelled M a r y e S because, of course. And so Burnside fails to get the pontoon bridges he needs to cross the river. His attack is delayed. When he finally gets them, he kind of rushes his men into battle because he's so excited. He finally gets to kind of carry out this campaign that he has planned. And the first wave of men cross the river, they begin to scale the heights, and they're just mowed down because, of course, the Confederates have the capacity sitting atop these heights, to absolutely kind of destroy the Union ranks. And when this first attack fails, Burnside says, we'll just send another wave. And that second wave experiences the same fate. And a third wave and a fourth wave. And by the end of it, Burnside is so fixated on this idea that simply sending another Wave of troops, another wave of men will dislodge the Confederates that he ends up sort of accounting for this massive amount of casualties. I mean, the ratio of casualties is more lopsided in this battle than in any battle in the Civil War. The Confederates barely lose a single soldier, and the Union army is scarred by this. I mean, they remember Fredericksburg for eons. And. And it's the fighting at Fredericksburg as Robert E. Lee kind of rides the heights and observes what is happening to the Union forces, to his enemy, that prompts Lee to observe, you know, his famous aphorism. It is well that war is so terrible, else we should grow too fond of it. That's in response to what his men are doing to Burnside's sort of tactical decisions. Burnside's effort to send just waves of men against this impenetrable position.
Don Wildman
His resume is amazing. Just as you're talking, I'm scrolling along the battles that he was involved with. It's extensive, to say the least. And it does go back to the Mexican American War as well. This man was involved from beginning to end of the preliminaries to the Civil War, and then all the way through to the Battle of the crater, 1864, in the siege of Petersburg, where he does okay.
Professor Cecily Zander
I mean, he does okay when he's not the guy at the top.
Don Wildman
Yeah.
Professor Cecily Zander
And I think this is an example, too, of military organizations needing to know the strengths and weaknesses of their soldiers. Not every general needs to be a commanding general, and Burnside is one of those cases. He was great as a subordinate. He should never have been put in the position to command an army.
Don Wildman
But his lasting legacy is the flip of his name. Okay. He had these amazing, you know, facial hair. And so they took Burnside and they switched it around, and it's now a sideburn.
Professor Cecily Zander
You.
Don Wildman
You grow your sideburns just because. In honor of Burnside. Kind of weird. All right, the last on our list, Major General Lloyd Friedenhall, who many people may have never heard of, World War II North Africa, is his, you know, staying on his character. Let's discuss where this guy comes from and why does he belong on this list?
Professor Cecily Zander
Well, he comes from Wyoming, of all places. So he was. He was born at a place called Fort D.A. russell, which is, you know, now the. The major sort of army fort outside of Cheyenne still today. His dad was in the US army, so he's the son of a soldier. He grows up at the very end of the frontier era of American history, sort of on one of the last true Frontiers of the American nation. He grew up with his dad having served in the Spanish American War and he pursues a West Point education. He fails out of West Point twice. Wyoming's senator was willing to appoint him to a third try at West Point, but he said, you know, maybe that's not for me. He goes to mit, he's finally commissioned a second lieutenant in the infantry. He, he goes to the Philippines and then he's in the first World War briefly though, makes no name for himself. And then he spends the interwar period on this amazing campaign of convincing everyone important in the United States army that he was the next great general, the kind of next great up and coming guy. I mean his self promotion campaign was quite remarkable. He had people like George Marshall convinced that he was going to lead the United States to victory in the next great war the nation faced.
Don Wildman
He had a disregard for military procedure. He gave weird orders. You know, he gave really weird, kind of convoluted things he would do almost like they were coded but it was just sort of badly done. Right?
Professor Cecily Zander
Yeah, he just would tell people sort of vaguely where to go. He referred to like shooty boys and walkie boys. He would never actually say like infantry and cavalry. And there seemed to be no reason for this other than, you know, kind of his own absurdity. The soldiers didn't care for it. Soldiers like to be told where to go and what to do to feel confident that their general knows what's going on. I don't think this guy ever gave an impression that he actually understood what was going on.
Don Wildman
Interesting. I mean I have a quote here. This is one of his orders that he wrote, have your boss report to the French gentleman whose name begins with a J at the place which begins with the D, which is five grid squares to the left of M. I don't even know how that works. But clearly a symptom of a larger problem. He never visited the front lines. He had a bunker built for him that was called, you know, in among troops, Lloyd's very last resort and Shangri La, a million miles from nowhere by his men. He demanded a bulletproof car like Dwight D. Eisenhower had. He wanted a, it was a bulletproof Cadillac. But his worst sin is the battle of Kasserine Pass against Erwin Rommel. This was one of those battles that you can watch movies about this. It's, it's a legendary, shameful moment when a general sets his troops up for the worst possible outcome.
Professor Cecily Zander
Yeah, yeah. You know we, we talk about generals who understand sort of combined assault the way to use multiple sort of important pieces to. To bring everything you have to bear on the enemy. This is not what happens at Kasserine Pass. This is just an absolute sort of disaster. And we should take a step back to say that the United States was operating in this battle under the command of the British First Army, Kenneth Anderson. And Anderson was a very good soldier and he could not for the life of him get Farindaal to listen to him, to follow his orders and to actually operate in concert. So that's the first problem. There is a sort of a joint operation that's supposed to be happening between two national armies that's not working out. And then the American commander doesn't tell his air support where they're supposed to be. He doesn't tell the troops where they're supposed to go with any kind of accuracy. And they're facing Erwin Rommel. That's not going to work.
Don Wildman
As a result, 7,000 men dead, wounded or taken. Soldier Crindall gives up, makes plans to destroy his own bunker before being finally reinforced by those accomplice. It's Vridenhall's incapacity for fighting that actually brings Patton into the war. Yeah. Patton is sent in to fix the problem and they are couldn't, you know, opposing characters completely. For all the good reasons for Patton but all the worst ones for Freedinal. Where does Freednall end up landing in this war?
Professor Cecily Zander
He's sent back stateside.
Don Wildman
Yeah.
Professor Cecily Zander
Sort of told, maybe trained some people. They're basically trying to make him feel important without giving him any real authority. It's remarkable. He's sort of disappeared.
Don Wildman
All right, I'm going to read off this list just to review. We covered a lot of territory. We started with Braxton Bragg of the Civil war, Confederate George McClellan, Union Army, Horatio Gates, Continental General. Then we went to William Hull, Charles Lee, Ambrose Burnside, and finally Major General Lloyd Predenhall, worst general. Cecily, who do you think?
Professor Cecily Zander
You know, George McClellan just stands out again. This was a guy that everybody needed to be good and he just couldn't rise to the occasion. But I think Charles Lee also, you know, constant insubordination trying to undermine your commander. That's really sort of tough to stomach. But in terms of putting their men at risk and unnecessarily exposing them to danger, I think our last candidate is probably up there as well.
Don Wildman
McClellan is humanized by our conversation and the reading I did before this. I didn't realize a lot of his flaw came from some of the good things that he. He felt about war. And, you know, I've never liked the guy, but, I mean, the truth is there were other elements at Braxton Bragg. You know, I just think he's just a vile person. Yeah. Beginning to end, tough character. Not a good general on top of it. So I'm going with him. Worst and most hated general Charles Lee is high on the list. And all these other guys, stinking bad ones, too. But there we go, folks. Thank you so much, Cecily, for joining us on this one. Always. I hope you'll come back again. I want to promote your book that people can read at the end of the summer, I suppose. Abraham Lincoln and the American West. I'm curious about that title. Why. So what's, what's the thesis of this book?
Professor Cecily Zander
So I just want to understand, sort of, you know, we, we always refer to Lincoln as a Westerner. And the, the idea of the book is what do we really mean by that? And then also, what was Lincoln's vision for the west during the Civil War? So this is a region we don't typically associate with this war that plays out in Virginia and Kentucky and Tennessee. But it. I think readers will be amazed about how much thinking Lincoln is thinking about Colorado and California and Oregon and all these places and what they pretend for the future of the country. So that's kind of what the book will do.
Don Wildman
I love that he had photographs of Yosemite that was, you know, he really understood that this was a whole unfolding era ahead, tragically so. All right, thank you so much, Cecily. We will see you again, maybe, about that book.
Professor Cecily Zander
Yeah. Thanks, Don.
Don Wildman
Hey, thanks for listening to American History hit. You know, every week we release new episodes, two new episodes dropping Mondays and Thursdays. All kinds of content from mysterious missing colonies to powerful political movements to some of the biggest battles across the centuries. Don't miss an episode by hitting like and follow. You help us out, which is great. But you'll also be reminded when our shows are on. And while you're at it, share it with a friend. American history hit with me, Don Wildman. So grateful for your support.
Raj
Hey, it's Raj and Noah. And we're back with a new season of Am I Doing It Wrong? The show that explores the all too human anxieties we have about trying to get our lives right.
Noah
Because we're still doing a lot of stuff wrong.
Raj
But who isn't? That's why each week we're talking about the topics that we could all use a little helping hit with, whether it's making new friends as an adult managing our emotions or even dreaming.
Noah
We'll be talking to experts in their fields who are definitely doing things right, so the rest of us can be a bit wiser and a lot better equipped to handle whatever life throws at us.
Raj
Subscribe now and listen to new episodes of Am I Doing It Wrong? Dropping every Thursday starting January 1st, wherever you get your podcasts.
Noah
And for the first time ever, we're going to have full video episodes on YouTube, because as long as there are things to get wrong, we're going to be right here to help you do them better.
Professor Cecily Zander
Love y'. All.
Raj
Lunch was great, but this traffic is awful.
Patient
Um, can we stop at a bathroom?
Professor Cecily Zander
Are you alright?
Patient
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Host: Don Wildman
Guest: Professor Cecily Zander, University of Wyoming
Release Date: January 26, 2026
In this episode, Don Wildman and returning Civil War historian Professor Cecily Zander explore the ignominious ranks of America's worst generals. Rather than celebrating those who led with brilliance, they dive into the spectacular shortcomings, ego-driven blunders, disastrous decisions, and leadership failures that have marred U.S. military history—from the Revolution to World War II. Their discussion brings incisive wit, vivid anecdotes, and thoughtful historical context, highlighting what not to do in command.
[05:02 – 06:04]
[06:04 – 14:29]
[14:29 – 22:51]
[26:37 – 33:39]
[33:39 – 35:26]
[37:56 – 39:32]
[39:32 – 43:01]
[43:12 – 48:05]
[37:03 – 37:56]
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[49:46 – 50:30]
This episode doesn't just roast a notorious collection of military failures—it illustrates the qualities that distinguish effective leadership from destructive command. The stories are often incredulous, sometimes darkly comic, and ultimately serve as cautionary tales from American history.