AFFotD Presents: Dunking on Old Timey Pictures of Civil War Generals

“Lol this is the dumbest thing we’ve ever written that’ll randomly make very uninteresting people very mad.”

~Our Lawyers

Image of Civil War battle

The Civil War is, apparently, a very complex and complicated subject, which is weird because it kind of seems that the two sides were “America” and “a group of people who wanted to not be part of America and lost, and wanted slaves” but maybe that’s just our silly American tendency to root for winners.

Anyway, if you’re here to examine the nuance of the Civil War’s socioeconomic impact on this country, or even hear a semi-coherent history of the war, we have terrible news. This article isn’t that.

But if you are here to see us post pictures of a bunch of Union and Confederate Generals and just roast them mercilessly because every Civil War General looked like a fucking Muppet, well, you’re in luck. Because we are here to prove that…

Every Picture of Every Civil War General Is Low-Key Hilarious

ulysses s grant

Union General and future-President Ulysses S. Grant, pictured shortly after soiling himself

The Civil War was truly a unique time for wartime photography. It was the first major war in American history that occurred after the invention of photography, but at the time photographic technology basically consisted of “you sit on a stool for thirty minutes while a technician shouts ‘TURN INTO A PICTURE’ at a piece of paper.” 

As a result, every picture of a Civil War general looks like they just spent two hours in line at the DMV. While we sympathize with that annoyance, we really don’t care. We’re still going to dunk on them. The only way our staff can feel anything is by insulting the appearance of old dead white men. It is our duty, and our curse. 

William Sherman

Picture of William Sherman

General William Tecumseh Sherman has been called the first “modern general.” He’s also well-known for his “total war” campaign that famously left Atlanta and much of the Western Theater burnt to the ground. He insisted on staying apolitical, and served as Commanding General of the U.S. Army under four different Presidents, holding the title for 13 years. 

But how does he look in this picture?

General Sherman looks like your alcoholic father who broke down crying after he missed the championship game because he was passed out at the bar. His pickup truck was made in 1996 and it’s rusted through.

He looks like he’s in debt to DraftKings, keeps a pint of Zackariah Harris in his glove compartment that opens when he drives over a bump, and last had carnal relations three weeks ago with a diner waitress named Jessica, or wait, was it Rebecca?

Dude looks like a homeless person about to bomb a job interview (just like how he bombed Atlanta amirite?). Ugh. We’re sorry for that one. Yeah let’s move on.

Braxton Bragg

Braxton Bragg

A weirdly large minority of America is vocally against renaming Fort Bragg, which was named after a fucking traitor and a loser, but we’re optimists here at AFFotD. We’d like to think that many of those who want the name to remain feel that way because, if it wasn’t for Bragg’s actively gross incompetence, we might not have won the Civil War

Dude straight up sucked—as the infallible source Wikipedia would put it, “Bragg was extremely unpopular with both the men and the officers of his command, who criticized him for numerous perceived faults, including poor battlefield strategy, a quick temper, and overzealous discipline.

Aside from sucking at his job, Bragg looked like Herman Munster had a kid with one of those Geico Cavemen. If that reference sounds old and out of touch, sorry, we must have been taking our cues from the kind of people who want Fort Bragg to keep its name.

We can do better. Dude looks like the World’s Most Interesting Man had a cousin who dropped out of high school to sell Meth and made it to the age of 45 without any interesting stories to tell about it. 

Dude looks like a half-shaved werewolf. Dude looks like he just shouted the R-word at a waiter. Dude looks like a racist PEZ dispenser. 

Braxton Bragg is washed, is what we’re trying to say.

Ambrose Burnside


Burnside is known for, well, sideburns, because, yes, the term comes from his last name, and holy shit, look at that work of Frank Gehry architecture on his constantly judging face. During the war, he had successful campaigns in Tennessee and North Carolina, but also suffered disastrous losses at Fredericksburg and The Battle of the Crater.

After the war, he was governor of Rhode Island for three years, Rhode Island’s Senator for six years, and was the first president of the National Rifle Association. So let’s say he has a slightly mixed track record. 

We know you’re expecting us to go after his facial hair choice. Hell no. Sure, does the male-pattern baldness and continuous facial hair have a bit of a Wooly Willy vibe to it? Absolutely. But the man cultivated a look and it was intentional and we’re here for it.

That said, he also looks like a cop who’s been on the same dull beat for the last 17 years, and is just waiting for an excuse to kick your ass. He looks like David Harbour’s disappointed uncle. He looks like he’s about to go viral for not wearing a mask in a Piggly Wiggly. 

His stache is sweet, though.

George Custer

George Custer

Listen…we all know why we all know who Custer is

Fun fact—he graduated at the bottom of his class from West Point, and that definitely tracks. Custer looks like the 23-year-old convenience store clerk that your parents are trying to get fired because he’s dating your 17-year-old sister. 

More than anyone else who served in the Civil War, he looks exactly like the kind of person who would skip their niece’s baptism to participate in a Civil War reenactment. 

This is the look of a man who has a list of his five favorite Swisher Sweet flavors aggressively committed to memory. Guy up here looks like he got fired from a carnival and stole a hat from the prize rack on the way out. If a man starting a tweet “well actually” gained human form, he’d look like General Custer. RIP we guess?

Robert E. Lee


Robert E. Lee of course led the Confederate Army and we’ll probably get in more trouble dunking on this guy than for anyone else on this list, for reasons that are likely dumb.

But dude’s cosplaying as a shitty Mark Twain, and we say that with all apologies to the Twain family. He looks like your 50-year-old bachelor uncle who always overdresses for family gatherings. If he were alive today, he’d be that guy who’s never watched Friends because “I don’t know, it seems too ethnic.” 

Robert E. Lee would 100% yell at a valet for taking too long to come back with his car, and probably doesn’t like black pepper because it’s “too spicy.” He looks like he was the kind of guy who’d post on Facebook about how he thinks libraries are a waste of money, followed by a shared post from an account called “Fun Adult Humor 🙃.”

George McClellan


McClellan is best known among our staff by being absolutely dragged through the mud in Ken Burns’ Civil War documentary, but he also is mostly known as a kind of shitty battlefield commander who was the fourth Commanding General of the U.S. Army, a position he held for…all of four months. 

He eventually unsuccessfully ran against Abraham Lincoln in the 1864 Presidential election, and ended up serving a single term as the governor of New Jersey in the late 1870s. 

Meanwhile, he is pictured above telling your non-conventional frat house full of free spirits that they are on double-secret probation. He’s VERY disappointed that you broke curfew.

We know he was a Union General who died in 1885 but he looks like Colonel Sanders’ son who pushed his dad out of the family business in a heartless hostile takeover. 

This man is wearing a uniform with an odd number of buttons, and he’s clearly upset that the picture was taken after his decision to stuff his hand in there led to the single stray button popping off.

Stonewall Jackson

stonewall jackson

Thomas “Stonewall” Jackson is widely considered one of the finest tacticians of the Civil War, if not of all of American history, his legend amplified by his tragic accidental and premature death. But he also fought against America, so fuck him, he looks like the ghost of a Russian Tsar in this picture. And not even one of the sympathetic ones. One of the mean ones who was pissed off he only had daughters. 

We’re not here to besmirch his ability as an officer, we’re just here to point out that, um, doesn’t he look exactly like Old Man Marley from Home Alone

Stonewall Jackson looks like someone who has a tire swing outside his house, but doesn’t have any kids, so why is it there?

Homeboy here looks like a character actor who almost always plays a farmer. He looks like the manager at a Casey’s disappointingly ringing up your purchase of condoms. 

Honestly, we could go with any picture of any Civil War General, and very easily dunk on them, but we decided to go with the most well-known names. You know, to make you mad! It’s honestly better for our traffic when you get mad! The internet is wild!

All we ask is, if you’re someone who finds the phrase “Robert E. Lee looks like he aggressively under-tips at a Denny’s after church” offensive…fucking why? Otherwise, if you know of goofy looking Civil War Generals that deserve some dunking, let us know! We’re sure there are dozens of them. 

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