Top 10 presidential betting stories

11 February 2016

By Clare Fitzgerald

Last Sunday after Super Bowl 50, on The Late Show with Stephen Colbert, President Obama shocked the nation when he admitted to illegally betting on the game. Or at least, I pretended to be shocked; I don't know about you. And to be fair to Obama, we don't know that he didn't pop out to Nevada on Air Force One to place a perfectly legal wager at a proper sportsbook. Although I also don't know if that would be a proper use of Air Force One.

Either way, Obama's sports wagering habits put him in good company. Other U.S. presidents have also enjoyed betting on a variety of games and events, going all the way back to the founding of our nation — and that's only because we didn't have presidents before then, not because we didn't have gambling.

So if you have this Monday off, feel free to spend it at your closest casino. Those dead presidents in your wallet would want you to. Don't believe me? Here are 10 of the best presidential betting stories from U.S. history:

10. The billiards room at Monticello

The Dome Room at the top of Thomas Jefferson's house is the subject of some historical controversy. It's most commonly known as the Billiards Room, for the simple enough reason that, for most of the 18th century, it had a bunch of pool tables in it, but historians disagree on if it was originally built to conceal illegal billiards tables or if it was initially just an observatory or ballroom. The folks at the official Monticello museum seem pretty adamant that the concealed billiards table legend is just a legend, citing Jefferson's Thoughts on Lotteries, where he disapproves of billiards in strong terms. But in Win or Lose: A Social History of Gambling in America<" rel="nofollow" the devil's game," Jefferson kept accounts of both his and Mrs. Jefferson's gambling wins and losses. This was typical T. Jeff — he was never one to let his own beautifully stated principles get in the way of doing whatever he wanted.

9. Warren G. Harding's — er, the White House's china

It's tough to find too many details about the card game where Harding gambled away this china set, probably because nobody wants to spend too much time writing about Warren G. Harding, one of our least effective presidents. Harding knew he was a useless president and preferred to spend his time playing poker and drinking bootleg liquor with his friends and other high-ranking officials. In addition to his other incompetencies, Harding seemed to have a fuzzy idea about what was actually his to gamble away: The china set in question had been at the White House since the second Harrison administration.

8. Obama's home poker game

Before he was the president and making appearances on all the hip comedy shows, Barack Obama was a freshman Illinois state senator and "kind of an egghead," lacking the political and business contacts needed to get things done in the notoriously cronyist world of Chicago politics. The solution? A poker game in the basement of freshman Senator Terry Link, where lobbyists, constituents and politicians of both parties could all get to know each other.

The game was referred to as "the Committee Meeting," which is a great name if you're deliberately trying to sound as much like a bunch of sketchy pinstripe-wearing Tammany Hall types as humanly possible.

7. Ulysses S. Grant's gambling problems

A fair amount of ink has been spilled about the connections between poker and politics, and how the skills required for the former are transferable to the latter. Writers and historians invariably point to the number of shrewd, effective 20th-century presidents who were also known to be excellent poker players, such as Roosevelt and Eisenhower, to support the idea.

The argument can also be made in the other direction. Case in point: Ulysses S. Grant.

Grant had never held elected office when he became President on the strength of his reputation as a fearsome battlefield commander during the Civil War. He went on to have a fairly disastrous administration and eventually died destitute after barely clawing his way out of significant debt. Much of this debt was from bad business deals, including a major investment in his son's financial firm that ended up going bankrupt when the other business partner, Ferdinand Ward, committed fraud and went to jail. But noted poker historians James McManus, author of Cowboys Full, and Vin Narayanan, Casino City's own former editor-in-chief, point out that Grant also lost a lot of money being terrible at poker.

One contemporary source insists that Grant was actually great at poker: Ferdinand Ward, Grant's son's fraud-committing business partner. In one account of a home game, Ward praises Grant's "firmness, tenacity of purpose and courage":

An incident occurred during one of our games which greatly impressed me at the time and which I never forgot. It gave me another flash at the General's secret of military success. Five of us were playing poker one night, and the party included General Grant and General "Phil" Sheridan, who were fast friends. General Sheridan was also inordinately fond of poker.

After the cards were dealt we all came in with the regular ante and we all stood for the raise. When cards were drawn General Grant took three and General Sheridan stood pat. He bet the limit. We all dropped out with the exception of General Grant. With his usual black stub of a cigar in his mouth he was a very formidable opponent for any one as he quietly looked Sheridan over, saw his bet and raised the limit. Sheridan promptly came back with another boost, and General Grant saw that and raised again. Then General Sheridan with his pat hand called. General Grant showed a pair of nines and won the pot, as Sheridan had nothing. General Grant laughed and said:--

"I knew you were bluffing, 'Phil,' and I would have kept it up until I had staked my pile."

And I firmly believe that General Grant, armed though he was with nothing more substantial than that measly little pair of nines, never had any doubt from the moment that he looked General Sheridan over that he would win the pot. He seemed to be possessed of a sort of sixth sense which enabled him to size up situations in a flash of intuition.

Grant may have won the hand and Ward's admiration, but this style of play doesn't seem to have netted him much profit in the long run. I'm inclined to trust McManus and Vin on this one and say Grant was probably as bad at poker as he was at investing and presidenting.

6. Eisenhower's deliberate poker loss

President Dwight D. Eisenhower was one of the real poker sharks among the presidents who have played, using his winnings to buy his first new military uniform and to buy gifts to court his wife. As he climbed the ranks, however, his sense of duty toward his subordinates eventually conflicted with his habit of taking all their money.

While at Ft. Meade in Maryland, Eisenhower's twice-weekly poker game with General (then Colonel) George Patton was supposed to be open only to "unmarried men who could afford to lose." Nevertheless, a married fellow soldier managed to lose quite a substantial amount of money to Eisenhower, and paid the debt with war bonds that his wife had painstakingly saved up.

Eisenhower felt bad about this, and conspired with some of his fellow players to lose the money back to the unfortunate soldier. The plot was "not achieved easily," according to Eisenhower. "One of the hardest things known to man is to make a fellow win in poker who plays as if bent on losing every nickel."

Eventually, they did get the soldier his money back, and Eisenhower then went straight to Colonel Patton and requested that the troops be banned from playing poker so the hapless man wouldn't be able to lose it again.

So fancy. (photo by the Harry S. Truman Library)

5. Harry Truman's Presidential poker chips

Perhaps no U.S. president is more identified with poker than Harry S. Truman, not because he was especially good but just because he played a lot. It was his main form of relaxation, and while he usually played for low stakes, he was not above splurging on the very finest equipment — including a custom seven-handed table for his yacht and a set of chips inlaid with the Presidential seal.

The chip set is currently in the possession of the Harry S. Truman Library. The fact that all the chips are accounted for has not stopped people from trying to run scams claiming to have more, of course.

If anybody is producing a straight-up replica set, however, I haven't been able to find it for sale online. Which is disappointing. Truman may have played poker to feel like a regular guy, but as a regular person myself, I want to feel fancy at my home games.

4. George Washington's stellar bankroll management

George Washington was a very serious, dignified, organized kind of guy who keenly felt the weight of history on him, so you might figure him as a prime candidate for being one of our rare presidents who didn't engage in gambling. However, the weight of history is a pretty heavy thing to cart around, and a dude has to relax sometimes.

We know George Washington gambled because he went about it in the most meticulous, George Washington way possible. He had a specific section of his budget for "Cards & Other Play," where he recorded the date, location, and amounts won and lost for every single gambling session. His gaming expenditures were modest, never amounting to more than a few dozen pounds per month, and he seems to have won at least as often as he lost. Our strategy writers would approve.

3. The Alexander Hamilton/Gouverneur Morris prop bet

Hamilton would later torpedo his own presidential ambitions by getting embroiled in the first sex scandal of our new nation, thus depriving himself of his rightful legacy as our best prop-betting president.

In addition to placing bets, George Washington was himself once the subject of a humorous proposition bet between Gouverneur Morris, the "Penman of the Constitution," and Alexander Hamilton, the ten-dollar Founding Father and subject of a hit Broadway musical.

At the Constitutional Convention of 1787, Hamilton bet Morris dinner and drinks for himself and a dozen friends that he wouldn't slap the dignified Washington on the back and greet him with familiarity — something that one simply did not do with General Washington. Morris accepted the challenge, clapping Washington jovially on the shoulder and exclaiming "My dear General, how happy I am to see you look so well!" which is more or less the 18th-century equivalent of a fistbump and a "What's up, bro?"

Washington didn't reply — he just stared Morris down until he backed off. Hamilton threw the dinner party, at which Morris is reported to have said, "I have won the bet, but paid dearly for it, and nothing could induce me to repeat it."

2. Andrew Jackson's duel over horse race betting

Andrew Jackson loved horses and horse racing, and is emphatically not known as one of our more even-tempered presidents. In addition to appraising, racing and breeding horses, Jackson also did a lot of betting on horse races, gambling away a good chunk of his fortune and, on at least one occasion, his clothes.

Things got especially serious in 1806 when a rival horse breeder named Charles Dickinson accused Jackson of reneging on a horse racing bet and insulted his wife. After a few more nasty back-and-forths, Jackson challenged Dickinson to a duel, which took place on May 30. Jackson took Dickinson's first bullet in the chest; then he shot, missed — then shot again, killing the other man.

Jackson was not charged with murder for this incident, because apparently it was entirely normal for guys in the early 1800s to have no chill whatsoever and to shoot at each other on a regular basis.

1. Richard Nixon's South Sea poker bar

It's fairly well known that Richard "Tricky Dick" Nixon funded his first election campaign with poker winnings from his time in the Navy, but without further elaboration, I think the picture most people have of this happening is of Nixon quietly socking away a succession of winnings from friendly home games (er, barracks games? bunk games? Where do Navy personnel live?). Apparently, this isn't the half of it.

According to this characteristically wacky article from Cracked, Nixon began his side career as an illegal gambling operator when he was merely in his teens, operating a shady wheel of fortune game at a carnival in Prescott, Arizona — which is most likely also where he learned to play poker. Later, as a Lieutenant Commander stationed in the Melanesian islands during World War II, Nixon built and operated an unlicensed casino bar called Nick's, where other members of the military could drop in for beer and high-stakes poker. It was here that "Iron Butt" — Nixon's real, actual nickname — would patiently fold hand after hand until he was in a position to extract large amounts of money from the other players. Nixon was so committed to his game that he once passed up an opportunity to meet celebrity aviator Charles Lindbergh, who was kind of a big deal at the time, in order to keep playing. Over the course of the war, Nixon may have made about $10,000, which was a lot more money in the '40s than it is now.

And that, friends, is how Nixon set himself on the path to the White House, where he would go on to make a big point of telling everybody that he was not a crook. Happy President's Day!