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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 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.
Major Jonathan Bratton
Love y'.
Don Wildman
All.
Walton Goggins
So you want to start a business? You might think you need a team of people and fancy tech skills, but you don't. You just need GoDaddy arrow. I'm Walton Goggins, and as an actor, I'm an expert in looking like I know what I'm doing even when I don't. And I like the sound of starting my own business. Walton Goggins Goggle glasses. But I'm an actor. I don't know what I'm doing. I needed help. GoDaddy Arrow uses AI to create everything you need to grow a business. It'll make you a unique logo, it'll create a custom website, it'll write social posts for you, and even set you up with a social media calendar. I didn't even realize I needed a social media calendar. GoDaddy Arrow will take your idea. That sounds good. And make a business that looks like you know what you're doing. GoDaddy Arrow can get your business up and running in minutes. You know what that sounds like? It sounds like a plan. Get started@godaddy.com aero that's godaddy.com airo Lunch.
Raj
Was great, but this traffic is awful.
Major Jonathan Bratton
Um, can we stop at a bathroom? Are you alright? 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 ep. 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.
Don Wildman
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 800-639-110 or visit creoninfo.com to learn more. That's creoninfo.com I'm asking my doctor about.
Raj
Epi and if Creon could help.
Don Wildman
Army, Marines, Air Force, Navy the room is a tapestry of dress blue and white uniforms. Rows and rows of high ranking members from every branch of the US Military stand at attention, shifting subtly on their feet in disciplined silence, eagerly awaiting a ceremony few ever witness. All eyes drift towards the velvet covered podium at the front of the room and more specifically to the small blue box positioned at its center. Inside of it lies a five pointed gold star on a field of blue. It is the Medal of Honor, the highest military decoration for valor, and since its creation in 1862, it has been awarded to 3,536 service members. But here's a question. Throughout our history, who of the greatest generals in our military has earned the Medal of Honor? And how did so many others not? Good day listeners. Don Wildman here. Thanks for tuning us in. From time to time on this series, we'll take a look at history from another angle. Not concentrate so much on a singular moment or pivotal event, but rather back up for a broader view. Make comparisons between different ages and iconic figures who commanded them, in this case, quite literally. Today on this episode, we're looking at who were the greatest generals of American history. We've shortlisted this to four the four greatest generals of U.S. american history. Understanding this is a slim number considering over 250 years, we've produced something like 4,000 generals across all the branches of the US military. So we've narrowed things down and such a conversation requires an expert. And once more, we're calling on our friend and frequent guest, Major Jonathan Bratton of the Maine National Guard, who. Who has served actively as an engineer officer, a sapper in the parlance, as well as command historian. Major Bratton is the author of to the Last Man, A National Guard Regiment in The Great War, 1917-1919, which chronicles the Guards 103rd Infantry Regiment in World War I. Cool stuff. Welcome, Jonathan. Welcome back to American history.
Major Jonathan Bratton
Thanks so much, Don. It's great to be here. Thanks for having me.
Don Wildman
So, Jonathan, we got four generals to explain today, but first I gotta ask a more general question. I'm curious. How do members of the military, such as your, think of generals? I mean, generally speaking, is it a stratospheric achievement? And explain what's with the stars?
Major Jonathan Bratton
Well, first of all, props for cramming in as many general puns as possible there. Well done. I raised my coffee cup to you, sir. Yeah, that's a great question. Because we sort of approach this militarily, right from the soldier background. We're usually. US Soldiers are pretty great. We tend to view everything through a very jaded and cynical perspective. So there's not a lot of sort of looking at the, oh, well, the stars fell down on their shoulders, so we obey them no matter what. There's always this healthy level of, you know, it's that leveling spirit of the American spirit. Right. That's just a little bit like, hey, well, you know, aspirational. I could be that someday. So I think over time it's changed. Absolutely. From the American Revolution, through the Civil War, world wars, to today, you have changing attitudes and norms and what's with the stars? Well, we. I don't think we have a long enough conversation to go back and look at our uniform and hero that we inherited from the British, stole from the French and Germans and Spanish and literally anyone else would give us pretty much anything. If you remember in the Revolution, it all started with a sash. So I think we should go back to that. I believe that. I think our general officer should wear sashes again. And this is my new move for general officer originalism, if you will.
Don Wildman
That might knock them down a few pegs. Right. But we do think of these guys as luminaries. I mean, of course, the five star general, it's just an untouchable position to be in. What makes a great general, in your opinion?
Major Jonathan Bratton
Oh, that's a tough one. I think as a soldier, you have to answer it as, are they looking out for me? Do they have my interests in mind as well as the mission? I think from the nation's perspective, you're Asking something similar, but with a little bit more focus on is this person going to get the job done? So many of those people that we talk about as quote, unquote, great generals are really very much personality based. Some of our best and most accomplished generals, we actually hear very, very little about simply because they kept their mouth shut and they did a great job. They were generally liked by their soldiers. Usually when we talk about a great general, they are a personality. People talked about them, they generated spots in the newspaper, they were part of the national dialogue. People are aware of them, that those Pattons, you know, come to mind, MacArthur's, etc. But they've got problems innate to them. So if you're a national leader, you're going to say, hey, is this general going to accomplish the mission while also not getting us in trouble more than, you know, assuming more risk than they need to. Whereas for a soldier, I think they're going to say, all right, do you give me victory, but also do you feed me, clothe me, pay me and allow me a sense of pride in myself?
Don Wildman
Interesting. It is a huge position. I mean, you're not only a leader of men, you're also a diplomat in many cases. You have to strategize for politicians as well as military, you know, the Department of Defense, you have to, you know, check all the boxes of all these different things. And I suppose back to my stars question, I was kind of confused about this. Each one of these stars marks a great moment of their career, an achievement of sorts. Or is this kind of more decorative?
Major Jonathan Bratton
So yes and no. I mean, and today, remember, a general officer in the US Military has to be confirmed by the Senate. So when you say that these are political positions, you are absolutely right. As soon as you go from the eagle to the star, you become a politician. And inherent to that there's a lot. Right. And so, yes, they are milestones we do tend to. We've changed things over time. Right. A brigadier general was so named because they commanded a brigade. Well, we have colonels command brigades now. So what does a brigadier general do? Well, most of the time it's almost a administrative position. So you're a general officer who's an administrator or you are a aide to a three star general. The two star, the major general, that's her point of real command a division, you know, that's a really critical moment. And then the three and four star positions are very pivotal. But there's only select spots for command for three and four star positions. And so much of that comes about by being an able administrator. This is not something that you know, we're going to cover sort of in talking about best generals, except to say the best generals have been the ones who have been able to, to be able administrators and logisticians. That is has been a key to the success as well as a charismatic attitude that can help people understand their vision and carry that forward.
Don Wildman
Cool. Well, let's start in the 20th century with the American general who is credited with winning the biggest and bloodiest war in the history of human civilization. Not bad for the resume. Dwight D. Eisenhower, coalition commander of the Allied forces in World War II. What sets this man apart? As you say, as much a political leader as a military commander. Right. Especially in this situation.
Major Jonathan Bratton
I think what makes Eisenhower so fascinating is prior to World War II he has not commanded any troops in combat. He hasn't. He spends World War I running a tank school at Gettysburg, Pennsylvania, Camp Colt. He will not over go overseas. So he's not, he hasn't had this formative piece of schooling and combat tutelage that all, almost all of his peers have. He is a guy though who is smart. He gets picked up repeatedly when MacArthur, when Douglas MacArthur is the army Chief of Staff, he taps Eisenhower to be one of his aides. He is consistently recognized by the big wigs in the army in this era. This is MacArthur and then George C. Marshall, who's someone who we should probably give at least a mention, probably the smartest guy to ever worthy in cloth of the nation honestly and serving it through multiple roles. But Marshall sees Eisenhower from 1940, 41, sees his skills and jumps him. I think it's over 300 people to push him up to the level of command for operations in North Africa in 1942, sort of this trial run. So why, why Eisenhower, incredible administrator, incredibly non controversial, accomplished person. And I think we really need to. When we look at the non controversial piece of this, what Marshall is asking Eisenhower to do is not hey, go lead American troops and American operations somewhere, it's go be an Allied commander amongst a bunch of allies. The historian Samuel Elliott Morrison, who's a naval officer, writes that in World War II, probably the greatest achievement, second only to beating the Axis the Allies had, was not going to war with each other. We're talking about massive personalities. You know, the British, Americans facing off constantly, let alone bringing in the French, the Italians once they switch side and you've got all the commonwealth countries and of course then there's Russia and you know, the Soviet Union. Not such all and not an easy guy to get along with. So you're asking Eisenhower to go be a diplomat, a general, a personal. You would almost call him like a therapist. You know, listen to these woes of these field commanders who are all, you know, he's got not just Patton, he's got Montgomery. He's got guys who are going to get kicked back to the American theater because they fail in North Africa. But yeah, so it's, he, he's, he's looking for someone who's not going to make a bunch of enemies. And Dwight David Eisenhower is exactly the right guy.
Don Wildman
This is the unusual era that we're in, which is America moving from, you know, this isolationist place over here to this massive leader of this massive new coalition, this Allied coalition. We play down the role World War I played in this. For a lot of these guys, this was the first time they were over there. Including, you know, Dwight Eisenhower, who wasn't. But the awareness of the fact that this was a new role for this nation to play, let alone an army to fight with, it was an incredibly different responsibility for anybody like an Eisenhower. He, as you say, excelled at the highest levels of logistical command. I mean, this would be, I think, going for any one of these guys we're going to talk about it was an incredibly sweeping thing. You know, it's just, it takes one's breath away when you consider what had to happen in World War II and the leaders that had to envision this and run it. I mean, it's extraordinary. It can't ever be said enough.
Major Jonathan Bratton
Cross continental logistics is just not something that you wave your hands and it happens. Especially when you consider the North Africa operations in 1942. So many of those troops actually embarked on. Not from England, not from the UK because we didn't have enough troops there. They embarked from the United States. They did a cross ocean landing in North Africa. So Eisenhower learned so much from the Tunisian North African campaign in 1942, rolling into 1943 invasion of Sicily. Again, learning really to understanding not just Allied but also joint operations. Now you've got to roll in the Navy and you, boy, you thought things were bad between the United States and the uk Bring in the, bring in the US Navy and the Royal Navy and the US army and the British army and oh my God, no one's talking the same languages. And there's the Air Force and you've got to think it's not just 3D chess. You understand why he smokes like five packs a day the entire war? Because he's trying to think on Multiple planes and dealing with just problems such as, you know, Vichy France, for example. He's got to go negotiate a way to try to get the French to quit fighting on the side of the Nazis, come over to the Allies, do it, allowing them to save face very similarly with the Italians. And this is all getting him prepared for that 1944 cross channel. Exactly. Invasion, D Day, you know, his most famous operation that most people know him for.
Don Wildman
Right. Well, I mean, let's just go. The list is extraordinary. Operation Torch, North Africa, you said Operation Husky. Sicily in Italy, Operation Overlord, which is what we're going to talk about. Normandy invasion, largest amphibious assault in history. I mean, unbelievable. And yet, you know, we have to remember we're talking about the headline stuff. There's all this stuff that happens in between, much of which is handled by assistants and people who are, you know, brigadier generals and the like. But there are these days of work that are constant and a lot of that has to do with managing personalities. So let's talk about D Day. How much was Eisenhower responsible for the look of this thing, the feeling of it, it was supposed to happen a year before, all kinds of logistics to manage. Was he really in charge of this thing as much as we think he is?
Major Jonathan Bratton
I mean, when it comes to, I think when you start looking at the responsibility, right, you know, he prepares a very famous letter on June 6 essentially to say in the event that we fail, it is all entirely my fault. Not the fault of any of my subordinates, any of my soldiers, airmen, Marine soldiers. Yeah, that's it. The buck stops there. That is the prime responsibility when it comes to shaping this thing. The time, not as much. That is the combined chiefs between the US and the UK are debating this. The US really wants to go soon. UK is saying, hold on, hold on, hold on. We tried this at Dapp, it did not go well. You guys need some more reps in. But then you've also got the Soviet Union that's saying, hey, we need this now, as you said, you know, they wanted this in 1943. The combined chiefs push it to 44. Once it becomes his responsibility, however, he is running everything from the troop build up the phony army, the rehearsal landings on the British coast and then that. Just like mind numbing, pulling your nails out, anxiety of will we get the best weather for this Cross Channel operation. He's the one who's making the call, hey, we got to push it and you know, from the end of May into June and then makes that decision on June 6th to go so the shape of it, how it looks, how it is prepared and then down to the very last details which I think are why, to me it's a mark of why I think Eisenhower is up here on this list of greats. Yes. He's not leading soldiers out in the field. He's not going to share these, the dangers. But he does go down prior to the invasion and goes down and starts talking to the airborne troops and he talks to any soldiers he can find prior to this invasion to just, you know, give him that idea that hey, I am there with you in spirit. I think it is one of Eisenhower's greatest regrets is that he never really did get to command troops in combat. He always had so many people looking down on him saying, oh well, you were just a, you were just a figurehead. You were just a sort of diplomatic commander. What he did is just so much more rigorous and it's hard because you can't, it doesn't have that. Everyone can sort of understand oh the dangers of combat, life or death. You know, it's sort of binary there. What he sort of goes through is this, you know, three and a half years of just sort of soul ringing tension and anxiety that is all bearing on him. And also the feeling of if he screws up, it is lives lost.
Don Wildman
Yeah, I mean I, he's top of my list. I'll just give it away. I just can't believe that this guy could live through this, let alone become victorious through it. I think what's fascinating about Eisenhower final note for me is that his effect is on the other end as well. You know, becoming president, he actually shapes so much of the 20th century for America's. The, the role of America in the world is due to Eisenhower, both as a general and a politician. It's outrageous what this guy pulls off and he does not get the credit where it's due. So for the next general, let's step back in time to the American Revolution. But no, not the obvious general you think I'm going to talk about, but rather I'd say the fighting Quaker Nathaniel Greene from Rhode Island. Okay. This is surprising to me that he landed on my list of four. Anyway, what sets Nathaniel Greene apart?
Major Jonathan Bratton
Nathaniel Greene is the everyman's soldier. He's not high profile. He's not the Benedict Arnold. He's not out there grabbing headlines either by, you know, crazy great things or crazy really bad things. He's not the Charles Lee who is also very, one of Washington subordinates is very loudmouth. He's also, he's also one of Washington's few generals who does not believe that he can do Washington's job better than Washington. Green is your pinch hitter. He's your go to guy. If things are messed up. He's the one that you turn to, to un mess it up. He's got a Quaker background coming out of Rhode Island. He sort of excused his family's Quakerism, ruins it by joining the, the Rhode island militia as a young man, the Kentish Guards. He doesn't have a crazy military background by the time of the Revolution, but he is a able organizer and administrator. And so he, when he brings in Rhode island troops during the siege of Boston and then when Washington takes over the army In July of 1775, this new weird formation called the Continental army, he recognizes very quickly, you know, who works and who doesn't, who's got the knowledge and who doesn't. And Greene is one who stands out almost immediately. And Washington, you know, recognizes that with a brigade command. And then he's going to continue recognizing, you know, what, what do we say is the reward for competency? More work. Right? That is Nathaniel Green all the way.
Don Wildman
Through Washington is credited with being, we're not going to win this as much as we're going to hold our own in this battle. I wonder how much of that comes from Nathaniel Greene, who until recently I really didn't understand played such a role in that vision.
Major Jonathan Bratton
So I think we really need to look for both of them at the New York, Manhattan, Long island Campaign of 1776, that summer and fall. That is so formative for both of them. Both of them go into that campaign with certain preconceived notions. One of them is, hey, we can hold positions through fortifications. We can basically strong point this war and force the British to maneuver in other directions. That is absolute failure. Forts Washington and Lee. Fort Washington is seized. Fort Lee is abandoned, nearly, almost taken. And both of those, both Washington and Greene play a role in these losses. Washington saying, hey, I'm not sure we can do this. Greene saying, no, no, we can definitely hold these fortifications. This is going to cost almost 4,000 continentals to be lost to prisoner of war ships in the Hudson and off Long island, where many of them will die of starvation and mistreatment, etc. And this is the key to, for both of them, the light goes on of, okay, no, we can't do this. If we want to win, we need to be mobile. We need to not rely on fixed positions and we need to be mobile. We have to have a Quartermaster and supply system that allows us to match the mobility that the Royal Navy gives the British army. And so to do that, Washington turns to poor Green and says, hey, man, hey, you're going to be my quartermaster. Not a glamorous role, but it's incredibly important. You know, the quartermaster provides all your food, all your equipment, your ammunition, etc. And as Green will famously say, no one ever heard of a quartermaster in history. So he got this great wry sense of humor as well as he then takes over Washington's logistics system, sets up an entire network of depots and arsenals to be able to allow Washington freedom of movement for his army between the Hudson Highlands down to Philadelphia. That is incredibly impressive. And so when we look at operations around Valley Forge, which to us, you know, our mind is like, oh, no, bad Valley Forge. Horrific starvation. It would have been a whole hell of a lot worse had Greene not been in charge of providing forage and sustenance to that army, as well as he conducts a grand forage, 1777-1778, I believe, which is essentially a combined arms operation to go out and seize food and fight the British for it if they find them. So he's given this independent command, and that's going to serve him very well when Washington taps him again and says, hey, so here's another part of the war that screwed up that I need you to take over in the South.
Don Wildman
Yeah, it's kind of a two part story for Greene in the Revolution. He's in the beginning quartermaster. He is fighting at the beginning, but he becomes more a logistics guy for Washington. But later he takes over more of a southern command. Right. And he applies everything that he's learned about sort of hit and run kind of tactics. You know, his phrase was, we fight. We get beat, rise and fight again. And that was the general strategy for this whole war, really. But winning by losing. His most famous battle, Guilford Courthouse, 1781. Late in the war, tactical defeats where American forces had to retreat after inflicting disproportionately high casualties on the British, harkens back to the Bunker Hill lessons. You know, that kind of way that they started to realize, oh, we could beat these guys just by, you know, making them bleed, but still, you know, holding our troops at bay. This leads to Cornwallis basically forced to retreat to the coast.
Major Jonathan Bratton
We don't give Green. Well, I think modern historians do give Green sort of enjoying a comeback moment. But really, when Greene moves further and further away from the cities, what he's doing is. And he's deliberately doing river crossings and seizing all boats, everything around him. So this. He understands that rivers in the south are key to mobility. And all he has to do is not lose his army. He can lose battles. He can't lose his army. By drawing Cornwallis away from his base of supplies and continuously pushing him, pushing his army to the point where it's nearing collapse, where it's in the middle of the backcountry, nowhere in North Carolina. And Cornwallis goes, you know what? Screw this. I can't. I have been fighting here for too long. I'm not making a difference. I have to go to Virginia. That's where the true source of the Continental army is also. I can't march anywhere else. And Greene does that to him. He wears out Cornwallis's army. He also wears out the British occupying force. Greene is going to continue in command in the south until 1783. He's going to continue fighting sort of a no win war in the south where this high level of brutality, it's very much almost a civil war. There's. And he's trying to sort of balance all this as well. So Greene, yes, his last three years of the war spent in the south with a very. A really rough situation, doesn't never have enough troops, never has enough manpower, never has enough supplies, but manages to pull a victory out of that. And that, I think, is. To me, that's almost like the stock image of American generalship.
Don Wildman
Wouldn't have won the revolution without this guy. From beginning to end, it was an incredible thing. All right, Jonathan, we're going to take a break. I want your opinion on the first two. Pick your best general out of these two.
Major Jonathan Bratton
Oh, man, they're so different. You've got. You got one who's commanding. It's got to be Eisenhower. The matter of scale is immense.
Don Wildman
It's Eisenhower. Not even a question in my mind. Okay, we'll come back after this break and we'll continue with our rankings.
Walton Goggins
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Noah
It'S Raj and Noah.
Raj
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 is it? 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, too.
Major Jonathan Bratton
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Don Wildman
Okay, we're back with Major Jonathan Bratton and our list of four greatest generals of American history. Jonathan. Two generals we're about to discuss are American icons. But still we're leaving out so many of the military minds, you know, that we ought to be talking about off this list. Patton, Bradley, Sherman, to name but a few American generals. American military expertise increases over our hundreds of years. Is this attributable to war, to war training, or did they just get better at figuring out what generals did? What an impossible question. I was just asking.
Major Jonathan Bratton
Conflict. The scale of conflict increases and the level of American military professionalism increases. Remember, basic, we didn't really have a war college or professional type of education system for anything beyond really lieutenants and captains until the 1870s, 1880s, really getting into the 1890s and the turn of the century. And the professionalism of Secretary of Defense Eli Haroot, who really creates the, what we consider the modern military establishment in the early 1900s, prior to that, remember, Revolutionary generation doesn't have West Point. We sort of go through phases as the military grows up, so to speak, and then the scale and complexity of warfare, which continues to this day. There's so many, many who say that, well, you know, we don't know how America would fare in the type of warfare that is going on in Ukraine, for example, which is different from what we have experienced ourselves. But that is the nature of war. It always changes. Yeah, that is the nature of all these people that we've been talking about. You know, the Mexican War was not the same thing as the Civil War for that generation. World War I was not World War II for that generation, etc. Etc.
Don Wildman
Yeah, the phrase is the times make the man. I mean, to paraphrase, in a way, the wars make the generals, don't they? I mean, the challenges they must meet create these guys. Okay, we're in the pantheon here, the last two generals. So obviously we're going to talk about George Washington, but his effectiveness as a military leader has been called into question over the years. Very surprisingly to me. He certainly had some ignominious episodes early in his career, before he was a general working for the British. Why was his legacy questioned? Why is it? And what in your mind redeems him?
Major Jonathan Bratton
So Washington's legacy has been questioned from the very moment that he first started his military career to the present day. I mean, he was questioned throughout the entire American Revolution by all of his subordinates, and justly so, I would say Washington's Record as a commander is mixed at best. If you were to look at sort of his ledger of wins and losses, it's pretty close to 50, 50, and it might even be a little bit more on the loss side. Begins his career pretty ingloriously with the Virginia Militia, you know, inadvertently doing his best, I would say. But presented with a situation that ends up with him starting a war with France, which is a rough thing to do when you're a lieutenant colonel of Virginia Militia in the back country of Pennsylvania in 1754, you will then have to surrender a force at for necessity. He's present at Braddock's defeat. He is present at a lot of failed British military operations. He does lead a brigade command in the Seven Years War, sort of the highest field command of an American, which sets him up for the Revolution. But what does set Washington aside, what sets Washington aside is that he can see beyond the small picture, he can see beyond the immediate loss and he can see mostly who can help him get to that next step, that next level. Well, he also doesn't know when he's beaten. That's a huge thing. I mean, you don't get a Trenton in Princeton from someone who only takes prudent risks. I mean that one is to attack in the winter with diminished forces. Just having been driven across two states, sorry, three states really is a hell of a lot. The other thing that makes Washington probably one of the most incredible generals is that he does have this strange knowledge of when to take risks. In 1777, he sends a big chunk of his army away to the north where he knows he's going to have to fight around Philadelphia against Howe's force in the South. But he sends a big chunk of his army and some of his best leaders north to Saratoga where he sees an opportunity. And what he sees in that strategic opportunity is the ability to capture an entire British army, which then changes the entire war. So one of his subordinates is going to get credit for it. But who shapes that campaign? It's Washington. That is an example of Washington's ability to think strategically, think beyond his own immediate needs, and then also to do the thing that Eisenhower did, which is to fight alongside allies and most importantly to keep Congress engaged in the war. I don't think people realize just how disengaged Congress was from the Revolutionary War. So he's dealing with politicians he's dealing with, so most of his soldiers are not paid the duration of a war. How do you keep that army in the field? That's almost mind boggling. And those are just day to day concerns.
Don Wildman
Leader of men is, you know, to say the least with this. But those men are not just the ones who are marching with them and fighting for them. It's the men who are making up a brand new government who are just figuring it out on their own. He's like an Eisenhower in that regard where he's, you know, shaping the vision of this country as it's in the works, let alone then becoming, you know, it's an insane achievement as a human being what he does.
Major Jonathan Bratton
He set standards that we hold today still. I mean the, the idea of a civilian control of the military, this is something that he set almost right off the bat saying, nope, I am a representative of the American government, which is a representative of the American people, therefore I serve the people. That is a thing that today we just take for granted that he sets that precedent. So there's so many things that he does that he sets his stamp on that are so important that we often just take for granted.
Don Wildman
Today I get emotional when I talk about Washington. An amazing human as your founding father in the Ken Burns New American Revolution. Starts out in that first episode saying there was never a more important revolution fought. And I was like, wow, that's true. The values that were created out of this revolution were completely, you know, new, or at least in the modern age, incredibly important. And therefore George Washington is at the head of that, you know, like that human enlightened movement he's doing as both a fighter and a politician. Incredible. There's a term that I'm curious about called Fabian strategy. What does that mean and how does it apply to George Washington?
Major Jonathan Bratton
That's a hand grenade to throw into a room of Revolutionary War historians if you ever want them to all start screaming at each other and maybe even fist fighting and clawing at each other. The idea of a Fabian strategy going back to a Roman general who lost campaigns but caused his enemy to take so many casualties that it was basically a strategy of victory by defeat, for lack of a better term, big argument about. All right, did Washington know what a Fabian strategy was? Did he even have a strategy? He does a few times articulate this idea of we are going to. Essentially we're going to fight them in a war of posts, AKA you know, we are not going to fight for position. We'll fight with maneuver. We will not fight. You know, one of his go to following New York is we're not fighting unless we've got a good chance of winning. I will trade ground happily all day long and you know, he trades Philadelphia, the nation's capital, in. In 1777, and says, hey, you can have it. You know, enjoy this place. Everyone here is arguing with each other. And here try to govern them. And after like six months, or, sorry, four months, how is like, like British General Howe is pulling his hair out and actually retires and goes back to the UK and leaves Henry Clinton in charge because he's like, can't stand these people.
Don Wildman
Philadelphia has that effect on people.
Major Jonathan Bratton
Exactly. Ungovernable. But in that time, you know, we see the loss of Philadelphia, you know, in our minds. Oh, what a defeat, A loss of a capital. Washington sees it as great. I can keep the British here all winter. They will sit here, and I can control the countryside, which is what he does from Valley Forge. You know, his raid at Germantown following Battle of Bandiran and the seizure of Philadelphia by the British. The Battle of Germantown is essentially a way of showing the British, hey, yeah, you can push outposts outside the city. I'm going to attack them every time you do. And Howe goes, I don't have enough troops for this. So he pulls all of his outposts back. And this is again, an example of how Washington sees the war, not as a series of wins and losses, but as a who can do this the longest? Because he knows if Congress is screaming at each other about how long this is going on, Parliament's no better. And Parliament is, as the war expands and as France gets involved in Spain and this turns into a global conflict, now Parliament has a lot larger things on its mind. And then as public opinion turns against the war. So this is what Washington is doing, the strategic thinking and doing it in a very adept way when literally everyone around him, not literally, but most of his subordinates all believe that they can do a better job than he. And some of them are sort of plotting to try to take him down. So highly, highly stressful situation all around.
Don Wildman
An amazing chess player on the battlefield and off without many pieces. I mean, it says a lot about the man. His success, you know, in the end, of course, results in the creation of the nation itself. And what more to say. They named the capital for him and a very big monument. Okay, we'll come back after this break and we'll continue with our rankings.
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Noah
It'S Raj and Noah.
Raj
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 and. And we're going to be right here to help you do them better.
Major Jonathan Bratton
Love y'.
Don Wildman
All. Jonathan, about the greatness of military leadership, I wonder, do you think the greatness of military leadership and vision only comes out of wartime experience? I mean, we're in an era when we're trying not to fight wars. Are we still going to produce excellent generals?
Major Jonathan Bratton
That's a great question. So, you know, we talked about how Eisenhower had no prior real wartime experience. George Marshall never commanded troops beyond the platoon level, didn't command troops in combat in World War I, was a staff officer throughout. My voting out of sequence for greatest would probably be George Marshall. He shaped half the world as we know it today. The Marshall Plan Reinvigorated Western Europe and huge chunks of Asia following World War II, let alone everything that he did in uniform, creating an army for war, prepared for World War II, and then everything he did anyway, World War I. But I would hazard to say, Don, I would go back. I would go one step further back in the question and say, is there such a thing as a great general, or do you have a. Can you have a great general with bad subordinates and bad troops? Troops? I don't think you can. I think you have to have a combination of a bunch of circumstances I'm not one for. I don't love the great man theory of history. I think able subordinates and the valor and courage of so many service members are what sort of these great generals are built on. And so I'm always. I always view them sort of with a little bit of a jaundiced eye of all right, you know, what are you taking credit for that some poor kid from Iowa did when the whole plan broke down, and then they got a medal of honor out of it, but then lost their own life. But that's my cynical approach.
Don Wildman
That's a great segue to our last great man, our last great general on this list, U.S. grant. So much to say, but like a Nathaniel Green in that he comes from that quartermaster mentality early in the war. He is so much a part of the supply chain and so forth, he is able to apply that to his battlefield expertise and then take it to another level in a way that surprised everyone. Right.
Major Jonathan Bratton
Grant's a fascinating guy, man. The hardest part about this, Don, is that we have to spend so little time on each of these guys when they could each be their own episode. This is a new, clever form of torment you've come up for me. But I enjoy, nonetheless the whole thing with Grant. He shares this thing with Washington where they don't know that they're supposed to have been beaten in. The key moment in this comes to the battle of Shiloh. The end of the first day when Grant has absolutely. His army has been pummeled. They're caught out in the open. They're pushed back miles. They're pushed to the bank of a river. Any military tactician would look at this and say, hey, you better dig in and just, you know, fight on the defense for all it's worth. You'll be lucky to escape annihilation. And Sherman comes up to Grant. It's raining at night under a tree. And Sherman says, well, we've had the devil's own day, Grant, haven't we And Grant says, sure have. Look them tomorrow, though. And that statement right there is that indomitable optimism and the belief that you can, either through your own will or ability or the trust in the strength of your own troops, change the equation. You know, for Grant, he knows Buell's army has just arrived. He's been reinforced. He attacks the next day, wins a great victory. It is sort of indicative of Grant that he is never going to accept this idea that, oh, I've been beaten, so I need to pull back and reset. That doesn't exist in his brain. I don't know how you build commanders like that. I don't know if you should build command. This is the whole problem about, like, building leaders for war. Is that a thing that we want to. Because without. Without so many other additional qualities, that could be a very, very dangerous thing. And you could end up losing an entire army. They have a couple other commanders in that war who don't have sort of accompanying personality features of prudency and equanimity and ability to see beyond your immediate surroundings. And they do lose entire armies, John Bell Hood, for example, as well as body parts. But the way that Grant is able to see past the immediate surroundings to the larger spectrum of conflict is truly impressive. And do it in a way that is humble, almost like uniquely American.
Don Wildman
I think, as you say, we could spend an hour and a half on these topics, but the Vicksburg campaign, a classic of military maneuvering, enormous story. The overland campaign, relentless, using forces. At that point, he's got them on his heels. But it's just. It takes a certain kind of personality to do what Grant was able to do to close the deal on the Civil War. And that's where he's blamed for being a sort of meat grinder. Yeah. I mean, many have accused Grant of being too vicious in his ability to spend his troops and others relentlessly. But this is what's always confused me about him, is how much did Grant understand what had gone wrong with the war prior to his taking over the general command? Or was he just going on his own instinct and saying, this is how you fight? Was he seeing himself as a corrective to what was so flawed about the Union strategy prior to his command?
Major Jonathan Bratton
I think, you see, when Grant comes east, you see him accompany the army of the Potomac, the main theater army in the Eastern Theater in 1864. See him accompany the army, not take command. So he's going and immediately starting to listen. You know, he places a lot of value in General George Meade's knowledge and understanding of the situation in the East. He also knows that his job, it is to provide vision and direction for that field army, but also to all the other field armies. When you look at his attempts at grand strategy to not just tie his operations into Virginia, into sort of what's happening in the east, you know, and along the realm of Petersburg, but also the Shenandoah Valley. But he's also looking at how is this tying into the western theater, how is this looking at tying into Sherman's operations into Georgia as well as the Navy's operations. So he's thinking holistically for the army of the Potomac. He fully understands the soldiers belief in themselves, that all they need is a general who will put the same faith in them that they have in themselves. And this is something that you begin to get this feeling From Chancellorsville in 1863, major defeat of the army of the Potomac. But the soldiers don't see it that way. They say, hey, we fought like hell. We did a great job. We just need a general who believes in us as much as we believe in ourselves. And they get that with Grant, yes, he is going to cause a lot of casualties in the. The Overland Campaign. That's mainly because the Overland campaign is simply a series of battles. Almost every three days there's a battle. It's pretty close in numbers to the Seven Days Campaign of George B. McClellan in 1862, who we never talk about as a bloody general, and yet bloodiest day of the Civil War is under his Command in Antietam, 1862. We don't talk about Robert E. Lee as one of the bloodiest generals of the war. And yet, but for him and so many of his attacks and also his decision to not stop fighting, we wouldn't have most of these battles. So war is bloody. And Grant's way of looking at it was the sooner we bring the war to an end, the sooner the dying stops. And any attempt to not fight it is simply going to prolong the death and destruction.
Don Wildman
And once again, we have a military leader who ends up being a president, a politician who has a huge role in reshaping the nation after the battle is done, so to speak. Doesn't go so well for Grant. He doesn't see his vision fully executed, but he does try. And it's a lot to be said for the guy. All right, we've done four generals. Let's wrap this up with a caveat. It's not fair what I'm about to do to you, but let's. Let's choose who's your favorite of these four generals in terms of their effect and impact on American history.
Major Jonathan Bratton
You know, if you just stopped at who's your favorite, that would have been one thing, their effect on American history. I'm going to go with Grant. Wow, really go with Grant on this one. I know, I know. I'm skipping over Washington. While Washington is important, I think what Grant does is even more important. It's one thing to sort of make a nation, it's another to keep it from absolutely collapsing, which all signs was pointing to in 1860s to 61. And Grant is the guy who pulls this out.
Don Wildman
Oh, I like this.
Major Jonathan Bratton
The Civil War is often called the second founding. Of course, Lincoln articulates that and Grant is the one who enables that is, and it's his also continuing to fall in line with the idea of this following his, his civil leadership. You know, Grant's not asking, hey, is abolition constitutional? Is any of this, you know, I, I don't know. Did you take my feelings into account about slavery when you did? No, he's just saying, okay, this is the law, I'm going to probably prosecute the law. He also does some stuff under, when he's the general of the army, when President Johnson is in power that we don't talk enough about in regards to preserving a lot of Lincoln's legacies where Johnson had wanted him to use the military to do some not great stuff in setting Johnson up politically and helping out some of his political buddies in the post war era. And then in Reconstruction as President Grant destroys the kkk. We forget about that one. He dismantles southern terrorist organizations while he's in power that are going to really, you know, the KKK doesn't show up again until the early 1900s in a totally new form. So all that to say I put in Grant up here because he enables a new birth of freedom that is the redefinition of the Declaration of Independence. That I think is for most of us closer to our idea of the Declaration's ideals than the Declaration itself in Washington's day. That's my argument and I stand on that Hill.
Don Wildman
I certainly agree with you in so many regards. Certainly the values involved in that reasoning. I'm going to go with Eisenhower myself because I believe that we live in a world that is demanding many of the values that he represents to me, which was a lot of on the American side, domestic side, the bipartisanship that he believed in and the restraint that he believed in. I think that without defeating fascism the way that that was done in World War II. We'd be, oh, boy, where would we be now? You know? And so any one of these four guys can claim the crown, of course. But we're gonna go with our choices for today. Major Jonathan Bratton has been our guest. Please look up the other episodes that he has been with us for. From Lexington and Concord to Bunker Hill and. And the invasion of Canada. There's even one on George Washington's generalship. And if you'd like to dive deeper there, just check our show website available a few clicks in where you get your podcast. Jonathan, I salute you. See you soon again.
Major Jonathan Bratton
Thanks so much.
Don Wildman
Hello folks. Thanks for listening to American History Hit. Each week we release new episodes, two new episodes dropping Mondays and Thursdays. All kinds of great content like, like 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 with a friend. American History hit with me, Don Wildman. So grateful for your support. Bye for now.
Noah
Hey, it's Raj and Noah.
Raj
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.
Major Jonathan Bratton
Love y'.
Don Wildman
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Host: Don Wildman
Guest: Major Jonathan Bratton (Maine National Guard, author, historian)
Date: January 19, 2026
This episode explores the question: Who are the greatest generals in American history? Instead of focusing on a single moment or event, host Don Wildman and guest Major Jonathan Bratton take a broad, comparative approach, choosing and analyzing four generals who represent pivotal moments in American military leadership. They examine what makes a great general, how U.S. military leadership has evolved, and compare the legacies and tactics of Eisenhower, Greene, Washington, and Grant. The discussion addresses not only battlefield triumphs but also logistical genius, political savvy, and lasting impact on the nation.
[05:06–09:49]
[09:49–18:35]
[18:35–26:22]
[29:56–31:43]
[31:43–39:42]
[43:38–49:46]
[50:20–52:28]
The conversation is historically rich but lively, peppered with humor and deep respect for the complexity of leadership. Bratton brings a soldier’s cynicism (“I always view them sort of with a little bit of a jaundiced eye of all right, you know, what are you taking credit for that some poor kid from Iowa did…” – 42:13), while Wildman is openly moved by the human dimension ("I get emotional when I talk about Washington" – 36:15). The episode blends big-picture analysis with memorable anecdotes and candid commentary on both the greatness and fallibility of these iconic leaders.
This episode shines a light on America’s military history through the lens of its most celebrated generals. By examining the personalities, decisions, and legacies of Eisenhower, Greene, Washington, and Grant, listeners gain an appreciation for the different qualities and contexts that produce greatness in military leadership. Major Bratton and Don Wildman bring both humor and insight, urging us to recognize not only the iconic “great men,” but the complexity, supporting cast, and circumstances that make nation-shaping leadership possible.