American History Hit – "America's Greatest General"

Host: Don Wildman
Guest: Major Jonathan Bratton (Maine National Guard, author, historian)
Date: January 19, 2026

Episode Overview

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.

Key Discussion Points & Insights

1. What Makes a Great General?

[05:06–09:49]

• Admiration and Skepticism: Soldiers are generally skeptical but aspirational about generals, seeing them both as luminaries and as human (“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.” – Bratton, 05:22)
• Beyond the Battlefield: Great generals must balance the interests of soldiers with the nation, master administration/logistics, radiate charisma, and be able to carry a vision forward.
  • “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.” – Bratton (06:46)
• Political Savvy: After a certain rank, a general is as much a politician as a soldier—Senate confirmation is required.

2. Dwight D. Eisenhower – Coalition Commander (WWII)

[09:49–18:35]

• Unorthodox Rise: Eisenhower was chosen to lead not due to combat experience but his exceptional administrative skill and ability to handle complex personalities (“What Marshall is asking Eisenhower to do is not hey, go lead American troops…it's go be an Allied commander amongst a bunch of allies.” – Bratton, 10:10)
• Logistics & Diplomacy: Eisenhower’s ability to coordinate Allied efforts (US, British, French, Soviets, etc.) was nearly as significant as winning the war itself.
• Personal Presence: Eisenhower felt regret about not commanding troops directly in combat, but he compensated by connecting with soldiers before D-Day and shouldering ultimate responsibility.
  • “He prepares a very famous letter on June 6…in the event that we fail, it is all entirely my fault.” – Bratton (16:04)
• Impact as President: Eisenhower’s influence extended beyond war, shaping mid-20th-century American policy and global standings.

3. Nathanael Greene – The Everyman's General (American Revolution)

[18:35–26:22]

• Unsung Hero: Unlike headline-grabbers or flamboyant generals, Greene played a crucial, often overlooked role (“Nathaniel Greene is the everyman's soldier. He's not high profile…he's your go to guy. If things are messed up.” – Bratton, 19:27)
• Logistical Genius: As quartermaster, Greene drastically improved Continental Army mobility and supply, especially vital during the hardship at Valley Forge.
• Southern Campaign: Greene’s hit-and-run tactics exhausted Cornwallis, leading to British retreat and eventual American victory.
  • “We fight. We get beat, rise and fight again.” – Wildman (24:22)

4. The Evolution of American Military Leadership

[29:56–31:43]

• Professionalization: The late 19th and early 20th centuries saw a major leap in military professionalism, with institutions like West Point and the War College becoming standard.
• Changing Contexts: Successive wars required very different types of generals, proving that “wars make the generals”—the demands of each era shaped the leaders who rose to prominence.

5. George Washington – Founding General and Strategic Visionary

[31:43–39:42]

• Contested Legacy: Washington's military record was mixed, with almost as many defeats as victories. Even during the Revolution, his leadership was questioned.
  • “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.” – Bratton (32:16)
• Strategic Patience: Washington’s genius was seeing the big picture—knowing when to fight, when to withdraw, and how to keep the Army and Congress together.
• Fabian Strategy: Rather than win every battle, Washington aimed to outlast the British, trading territory for time and wearing down the enemy.
  • “He does a few times articulate this idea of…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.” – Bratton (36:54)
• Setting Precedents: Washington established civilian control over the military, a cornerstone of American democracy.

6. Ulysses S. Grant – Relentless in Pursuit of Union Victory

[43:38–49:46]

• Dogged Determination: Grant’s refusal to be defeated—exemplified at the Battle of Shiloh—is legendary.
  • “Sherman says, well, we've had the devil's own day, Grant, haven't we? And Grant says, sure have. Lick 'em tomorrow, though.” – Bratton (44:03)
• Holistic Strategy: Grant not only applied logistical wisdom (a la Greene) and relentless pressure but also engineered campaigns across multiple theaters (Vicksburg, Overland Campaign).
• Misunderstood as ‘Butcher’: The high casualties under Grant were a result of the nature of Civil War battles and his resolve to see the war to a close, rather than his disregard for life.
  • “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.” – Bratton (49:46)
• Postwar Legacy: As president, Grant tried to fulfill Lincoln’s legacy, fought the KKK, and defined Reconstruction-era justice.

7. The Final Ranking: Who Was America's Greatest General?

[50:20–52:28]

• Bratton chooses Grant: "It's one thing to sort of make a nation, it's another to keep it from absolutely collapsing…Grant is the guy who pulls this out." – Bratton (50:54)
  • Grant as the enabler of America's "second founding," upholding constitutional ideals even after war.
• Wildman chooses Eisenhower: "I believe that we live in a world that is demanding many of the values that he represents to me…" – Wildman (52:28)
  • Eisenhower as model of modern leadership, both in defeating fascism and shaping mid-20th-century American democracy.
• Acknowledgement: Any of the four could claim the crown; different eras require different kinds of greatness.

Notable Quotes & Memorable Moments

• On Eisenhower:
  • “He is a guy who is smart…picked up repeatedly…incredible administrator, incredibly non controversial, accomplished person.”
    — Bratton (10:10)
• On Greene:
  • “He’s not the Benedict Arnold…he's 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.”
    — Bratton (19:27)
• On Washington:
  • “What does set 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.”
    — Bratton (32:51)
• On Grant's Mentality:
  • “‘Well, we've had the devil's own day, Grant, haven't we?’ And Grant says, ‘Sure have. Look them tomorrow, though.’”
    — Bratton (44:03)
• On Legacy:
  • “It's one thing to sort of make a nation, it's another to keep it from absolutely collapsing…Grant is the guy who pulls this out.”
    — Bratton (50:54)

Timestamps for Key Segments

• [05:03] – Bratton on how military views generals & what makes them great
• [09:49]-[18:35] – Analysis of Eisenhower’s WWII leadership and administration
• [19:27]-[26:22] – Greene’s overlooked contributions, quartermaster role, and Southern campaign
• [31:43]-[39:42] – Washington’s strategic approach, contested legacy, and the "Fabian Strategy"
• [43:38]-[49:46] – Grant’s Civil War leadership, strategy, and reputation
• [50:20]-[52:28] – Final ranking and personal picks by Bratton and Wildman

Tone and Style

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.

Summary

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.