There have been many famous cigar smokers in history, and many of them are national leaders like Churchill, JFK, and Castro. But before you kick back and enjoy a victory cigar, you first need a victory. This got us wondering, out of all the tough, cigar-smoking bastards who ever held the nation’s highest office, who were the toughest? After all, there’s a pretty broad spectrum of types who become president, whether they shopped cigars online in the digital age or could only dream of such luxury.
While we’ve seen war heroes and generals, we’ve also seen lawyers, businessmen, and other cigar smokers who didn’t have a life anywhere near as hard as some of our Founding Fathers. When you light up a premium cigar and enjoy your favorite tobacco products, you join their ranks!
So here, in no particular order, is a list of some of the toughest cigar-smoking U.S. Presidents to ever walk their giant balls through the front door of the White House (George Washington would have, but it wasn’t built in time). Let’s start with him.
A disclaimer, though: we just don’t have time to detail the exploits of every President or even hit on all the crazy stuff the cigar smokers on this list have done. If you spot an egregious omission, please drop it in the comments below. We’re fortunate to live in a country with such a rich history of badassitude that we can’t squeeze it all into one article!
The dude was 6’2”, 200. He was built. And the Lord blessed him with a body that was strong enough to persevere through ridiculously difficult conditions and help forge a nation. He led America’s forces through eight years of the Revolutionary War, holding a ragtag bunch of barely-trained and barely-equipped patriots through the mouth of hell and out the other side to victory. He was known for leading charges, like in the 1775 Battle of Monongahela, where two horses were shot out from under him and his coat showed four bullet holes at the end of the day.
(George Bush the First would later echo this performance and one-up it by having a plane shot out from under him and being the only survivor of a disastrous mission over Chichijima island in Japan during World War 2. We’d order cigars online to share with HW and GW alike.).
Other famous smoke lovers on this list were shot and lived to tell the tale, so we’ll have to wait to hear more about that.
On top of Washington’s valor, there are many mythical (or not) feats of strength ascribed to Washington, like throwing a stone on top of Virginia’s Natural Bridge. It’s 215 feet high from the riverbed! It’s a hell of a toss if he did it. If anyone deserves to have a cigar lit up to them, it‘s a man like that.
Lincoln is naturally remembered for his role as a leader during the Civil War, but we wanted to highlight something a bit different that you might not know about. The guy is in the National Wrestling Hall of Fame! The 6’4” Railsplitter had a ridiculous record, with only one recorded loss in a dozen years of competition. And plenty of this was catch wrestling, which is a far broader ruleset than modern wrestlers would be familiar with—including the use of various submission holds.
The dude was a problem! You seriously didn’t want him to lay hands on you. The Wrestling Hall of Fame description also reports that “at age 19, [Lincoln] defended his stepbrother's river barge from Natchez thugs by throwing the hijackers overboard.”
Challenge him if you want to get embarrassed.
Like Washington, he also came complete with his own stories of strength and endurance. One such story is that Lincoln may have chopped a cord of wood (it’s a ton if you’re an urbanite and haven’t seen anyone’s winter supply recently) and could still hold his axe out steady after.
Next, let’s cover a man’s man you probably had in your mind as soon as you saw the title of this post—of course Theodore Roosevelt would have shopped cigars online to celebrate all his most incredible wins.
Asthmatic and still may have smoked cigars.
Served as a famously anti-corruption head of the New York Police Department.
Led the “Rough Riders” volunteer cavalry unit during the Spanish-American War.
Loved combat sports and was a judo brown belt who threw people around in the White House.
Was shot and still gave a speech.
Let’s delve into that one to get the insane facts.
The bullet lodged in his chest after going through his glasses case and a copy of a speech. Roosevelt noticed that he wasn’t coughing up blood, and so wasn’t lung-shot. He decided to delay the hospital trip and instead gave a 90-minute speech! There are a lot of guys who couldn’t do a friggin Zoom call in that condition, but, as history records, “It takes more than that to kill a Bull Moose.”
The bullet was left in place and Roosevelt simply carried it for the rest of his life.
He also had a great heart. He won a Nobel Peace Prize and set aside National Parks and other lands for the perpetual enjoyment of future generations.
What a titan.
His exploits were nothing compared to some of the men on this list, but as a member of two National Championship football teams at the University of Michigan, he was undoubtedly tough. He played friggin center, and linebacker, and was also the team’s long snapper. In fact, before deciding to go to Yale Law, he was courted by both the Lions and Packers.
If you ever get a time machine, see if you can organize a wrestling match between him and Lincoln. Could be amazing! Hell, make it a round-robin with Roosevelt (a little undersized to go with these 6+ footers, though). Take the time to order cigars online for the champ, or split those stogies four ways and sit down for a smoke with these legends.
Ok. We’re back to legends of manliness with “Old Hickory,” Andrew Jackson. Not only was he a famous general with numerous battle exploits to his name, but he was also a prolific duelist. History records him as participating in something like a hundred? Hard to believe, but in all that dueling, he only killed one man. The man was Charles Dickinson, and he had insulted Jackson’s wife. Jackson missed his first shot and then breached the code duello by re-cocking and firing again, killing Dickinson.
He joined the army at age 12. That's right; 12! When a modern child would be playing Call of Duty online and talking shit while eating Hot Cheetos, Andrew Jackson was marching in the real thing and 360 no-scoping the British redcoats while eating hardtack rations.
Jackson survived an assassination attempt (two misfires!) at age 67 and busted out his hickory cane to give the would-be assassin a thrashing.
This was not a man to be trifled with, at all.
The man they called “Old Rough and Ready” helped win America’s first victory of the War of 1812 by repelling an attack on Fort Harrison. He went on to have three decades of military service and ascended to the Nation’s highest office in 1849 when North and South were on the brink of deadly conflict. He had a reputation for being the type of commander who would have his boots in the mud right alongside his men.
Perhaps his greatest victory is the taking of Monterrey in the Mexican-American War, and then holding out in the town of Saltillo against a massive force commanded by Mexican General Santa Anna at the Battle of Buena Vista. He forced the Mexican retreat, which heralded a victory for America in the broader conflict.
Undoubtedly, there are more profiles in courage that we don’t have time for here, but this list gives you a feel for just how brutal some of our national leaders have been. These were men who absolutely would not back down from a fight of any kind, even with their lives on the line. It’s no secret why they commanded such respect from the men of their time.
When you order your next batch of cigars online, dedicate a puff from your premium cigar to one of these legends of manliness. You’ll be smoking cigars in great company!