American History Hit: "America's Worst General"

Host: Don Wildman
Guest: Professor Cecily Zander, University of Wyoming
Release Date: January 26, 2026

Episode Overview

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.

What Makes a Bad General?

[05:02 – 06:04]

• Don sets the stage: "So what qualifies a bad general in general?"
• Cecily outlines two main failings:
  • Ego: "Inability to put ego aside... didn't feel the need to consult anyone else or to get along with anyone else." (Cecily Zander, 05:24)
  • Relational skills: A great general must get along with superiors and subordinates; many on the list failed at this, sometimes sabotaging their own side.
• Other critical flaws mentioned: lacking tactical ability, avoiding responsibility, and sometimes cowardice.

Key Discussion Points and Generals

1. Braxton Bragg – Confederate General, Civil War

[06:04 – 14:29]

• Personality and reputation:
  • "Possibly the most hated general on our list." (Don, 06:04)
  • Bragg's notoriously bad temperament—couldn’t get along with anyone, often argued even with himself (famous requisition anecdote).
  • "My God, Mr. Bragg, you've quarreled with every man in this army and now you're quarreling with yourself." (Cecily, 07:50)
• Tactical failures:
  • Prone to fixate on imaginary threats, leading to indecision; blamed failures on subordinates.
  • His 1862 Kentucky campaign ended in mass retreat, abandoning Kentucky and deserting thousands of rifles. ("He essentially abandons Kentucky for the remainder of the war." – Cecily, 10:40)
  • Chickamauga: His only win, which was mostly due to Union error; failed to follow up or exploit his rare victory.
• Legacy:
  • He lost defensible positions, demoralized troops, and was widely despised. Even survived an internal assassination attempt.
  • Notorious for harshly punishing his men—executed a 19-year-old deserter, further eroding troop morale.

2. George McClellan – Union General, Civil War

[14:29 – 22:51]

• Strengths and weaknesses:
  • Gifted organizer, renowned for building and training the Army of the Potomac; beloved by soldiers ("Little Mac").
  • Fatal flaw: Chronic over-preparation and hesitation—“a case of the slows.”
• Battle of Antietam:
  • Even with enemy plans in hand, failed to win decisively or pursue Lee—"He simply doesn't understand. He's trying...to push McClellan to move. But even with his enemy's battle plans...he lets the great confederate commander get away." (Cecily, 16:55)
• Psychology and politics:
  • Over-cautious, often imagined threats and "bugbears."
  • Politically and temperamentally conservative; minimized aggression in hopes of postwar reconciliation.
  • Don: "It's almost like he was a victim of his own logistical intelligence...you end up hamstringing yourself and not taking action." (19:41)
• Personality:
  • Grandiose self-image, as revealed in letters to his wife.
  • Could not accept high casualties—"If McClellan had ever been labeled a butcher, it would have crushed him." (Cecily, 21:42)
• Summary:
  • Lacked vision, risk-taking, and pluck despite his organizational talents.

3. Charles Lee – Major General, Continental Army

[26:37 – 33:39]

• Background:
  • Entered the Revolution with more military experience than almost anyone else, but deep resentment at not being chosen to command.
  • "When you think from the very beginning you should have been the guy...they pick somebody named George Washington, you're going to have a problem." (Cecily, 27:04)
• Downfall:
  • Captured by the British early; possibly divulged American strategies while a prisoner.
  • At the Battle of Monmouth, ignored direct orders, executed a disastrous retreat, and publicly argued with Washington.
  • Was court-martialed for disobedience. "Shouted at George Washington...it's not a good look." (Don, 32:18)
• End:
  • Retired in disgrace, died in debt and obscurity. "One Lee that is among the great names and then one Lee among the worst." (Cecily, 33:05)

4. Horatio Gates – Continental General, Revolutionary War

[33:39 – 35:26]

• Strengths:
  • Excellent administrator.
• Weaknesses:
  • Overstated his achievements (notably at Saratoga).
  • Suffered catastrophic defeat at Camden by tactically mismanaging troop placement against the British. "He forgot basic information...just a disaster." (Cecily, 34:10)

5. William Hull – War of 1812

[37:56 – 39:32]

• Incident:
  • Surrendered Fort Detroit and Michigan to the British without a fight, fearing for civilian safety and his family.
• Consequences:
  • Court-martialed and sentenced to death (later pardoned).
• Analysis:
  • Not motivated by cowardice, but by demoralization after being ignored by leadership. "He was unwilling to fight for a government that he didn't feel was going to back him up." (Cecily, 38:47)

6. Ambrose Burnside – Union General, Civil War

[39:32 – 43:01]

• Famous for:
  • The disastrous Battle of Fredericksburg: Repeatedly sent waves of men into a slaughter, ignoring the futility of the attacks.
  • Ratio of casualties lopsided—Union losses catastrophic, Confederates barely harmed.
• Quote:
  • “He sort of demonstrates a stunning inability to learn from the failure of a tactical choice about seven times over.” (Cecily, 39:50)
• Other roles:
  • Served best as a subordinate—not meant for high command.
  • Legacy: Gave his name (accidentally) to "sideburns" due to his distinctive facial hair.

7. Lloyd Fredendall – Major General, WWII (North Africa)

[43:12 – 48:05]

• Background:
  • West Point washout, self-promoter, ended up in high command through relentless networking.
• Command style:
  • Issued obtuse, confusing orders (e.g., “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.” — [45:29])
  • Avoided the front, hid in a heavily fortified bunker nicknamed “Lloyd’s very last resort” by the troops.
• Disaster at Kasserine Pass:
  • Failed to coordinate with British, kept troops and air support in the dark, leading to catastrophic losses against Rommel.
  • "It was just an absolute sort of disaster...they're facing Erwin Rommel. That's not going to work." (Cecily, 46:21)
• Aftermath:
  • Relieved of command, sent home to train recruits—effectively exiled.

Reflections on Leadership and Responsibility

[37:03 – 37:56]

• Cecily: “The ability...to take responsibility for failures that aren't necessarily your fault...Grant, Washington, Eisenhower could do because they were the man at the top...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.” (Cecily, 37:29)

Memorable Quotes & Moments

• On Bragg's Personality:
  • "He truly looks like a Muppet more than a human being." (Cecily, 06:32)
  • "Mr. Bragg, you've quarreled with every man in this army and now you're quarreling with yourself." (Cecily, 07:50)
• On McClellan:
  • "He has a case of the slows." (Don, 15:44)
  • After Antietam: "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." (Cecily, 17:10)
• On Burnside at Fredericksburg:
  • “Burnside fails to get the pontoon bridges he needs...when he finally gets them, he kind of rushes his men into battle...the first wave of men cross...they're just mowed down.” (Cecily, 39:50)
  • "The ratio of casualties is more lopsided in this battle than in any battle in the Civil War." (Cecily, 41:22)
• On Lloyd Fredendall’s orders:
  • “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.” (Don, 45:29)
• On Charles Lee’s insubordination:
  • “You don't fully commit your men. And then the retreat...is absolutely disastrous.” (Cecily, 30:39)
  • "There was a moment when he actually shouts at George Washington...it's not a good look." (Don, 32:18)

Who Was the Worst?

[48:05 – 49:46]

• Cecily: "George McClellan just stands out...everybody needed him to be good and he just couldn't rise to the occasion. But I think Charles Lee also, constant insubordination...putting their men at risk...I think our last candidate [Fredendall] is probably up there as well." (Cecily, 48:31)
• Don’s pick: "Braxton Bragg...he's just a vile person...Worst and most hated general. Charles Lee is high on the list, and all these other guys, stinking bad ones too." (Don, 49:00)

Cecily Zander’s Book Plug

[49:46 – 50:30]

• Abraham Lincoln and the American West (coming summer): Examines what being a “Westerner” meant for Lincoln and his vision for the West during the Civil War, including the importance of future states like California, Oregon, and Colorado.

Notable Timestamps

• 05:24 – Qualities that define a bad general
• 06:30 – Introduction to Braxton Bragg’s personality
• 09:57 – Bragg’s failed Kentucky campaign
• 15:44 – McClellan’s chronic hesitation at Antietam
• 21:03 – Letters to McClellan’s wife reveal his ego
• 27:04 – Charles Lee’s resentment and insubordination
• 30:39 – Lee’s disaster at Monmouth
• 39:50 – Burnside’s repeated failures at Fredericksburg
• 45:29 – Fredendall’s infamous coded orders

Takeaway

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.