'All in' showdown: How an SF amateur nearly beat 1,781 players in a $900K poker tournament He went to Vegas for a bachelor's party, entered a hold 'em tournament on a lark

Doug Gladstone makes a bet at a Deep Stack Texas Hold 'Em tournament at the Venetian Resort in Las Vegas. Doug Gladstone makes a bet at a Deep Stack Texas Hold 'Em tournament at the Venetian Resort in Las Vegas. Photo: Courtesy Of Doug Gladstone Photo: Courtesy Of Doug Gladstone Image 1 of / 12 Caption Close 'All in' showdown: How an SF amateur nearly beat 1,781 players in a $900K poker tournament 1 / 12 Back to Gallery

Venetian Resort casino, 4:30 a.m. July 4, 2019:

Doug Gladstone peels up the edges of the two "hole" cards he has been dealt and takes a peek.

Ace and king of diamonds.

A total of 1,781 people, most of them professional poker players, had entered the three-day Deep Stack Texas Hold 'Em tournament at Las Vegas' Venetian Resort. Now just four remain, including Gladstone, a 49-year-old San Francisco tech executive recruiter.

Gladstone is no pro, but he does know Texas Hold 'Em. He normally only plays cash games with friends and at local Bay Area casinos. But here he is at the final table of a major Vegas tournament with a $500,000 minimum guaranteed payout. And he has the biggest chip stack.

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Ace-king suited is a very strong hand, especially at the end stage of a tournament. Gladstone bets 4 million of his 23 million chips.

His main rival, a 30-ish bearded Canadian wearing a Toronto Blue Jays cap, pushes all of his 21 million chips in.

What Gladstone does next is critical. If he wins the hand, he takes a commanding lead in the tourney, making him the odds-on favorite of taking home $146,000 in first-place prize money. A loss would cripple him, virtually ending his tournament. A fold means he stays alive, albeit with 4 million fewer chips.

He calls.

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With the rise in online poker in recent years, Texas Hold 'Em has skyrocketed in popularity. Major tournaments are televised on ESPN and other sports networks.

In the game, two "hole" cards are dealt face down to each player, and then five community cards are dealt face up in three stages — three cards (the "flop"), a single card (the "turn") and one final card (the "river"). After each stage, players make bets on their hands. When a player bets "all-in," he is committing all his chips.

Hold 'Em is the only game Doug Gladstone plays and one he has enjoyed since college — "mostly small games, win 50 bucks, lose 50 bucks." He says he does not play tournaments.

"I just really like the game," says Gladstone, who places C-level executives in technology jobs for Odgers Berndtson in San Francisco. "I have a financial background, multiple degrees in finance. I have a statistical mind. And so I was drawn to beating the game from missed bets and when I saw arbitrage opportunities. And when people made mathematical betting mistakes, I felt that with my statistical mathematical background I had an edge."

But at first, mathematics prowess went only so far.

"I really didn't understand the strategy of poker and the game," he said. "I used the math and it helped me, but I wasn't applying all the other elements of poker correctly."

After years of playing, he says he now wins at small-stakes games about seven out of 10 times.

In Vegas for a bachelor's party, not poker

The last weekend in June, Gladstone joined friends for a bachelor's party in Las Vegas. On the following Monday morning, before he was scheduled to fly back, he happened by the Venetian Resort, which was advertising a Deep Stack tournament with a $500,000 minimum payout and a $600 entry fee.

The risk-reward ratio was favorable.

"You know what, I'm just going to enter this tournament," Gladstone told himself.

One thing that makes playing poker tournaments much different from cash games is the ante, or "blind," structure.

In tournaments, antes go up every 30 minutes, effectively forcing the player to compete. If you're not getting cards, you're going to be "blinded" out by the rising ante structure. In cash games, you have all the time in the world. If you're losing, you can simply pull out more cash to replenish your chip stack.

In a tournament, once you're out of chips, you're done.

After the first day of play against the roughly 900 players in his heat, Gladstone had 285,000 chips, more than 10 times his buy-in of 25,000, good enough to advance to the next round.



He blew off his flight back to San Francisco.

On Tuesday, he had the day off as the second heat — the other 900 players — competed.

About 380 to 390 players survived the two-day gauntlet. Gladstone showed up for the noon Wednesday start in his usual poker regalia — t-shirt, sweat pants, hoodie, baseball cap and sunglasses. He carried a backpack stuffed with music, headphones, candy, bars, nuts, bananas, Power Bars and water.

Tournament poker is an endurance sport. Play can go on for 17 or 18 hours straight with only occasional breaks, including about an hour for dinner. Keeping yourself fed and hydrated is important.

"You need to be drinking water," Gladstone said. "The players that drink alcohol, so be it. That can induce poor decisions. For myself, I only drink water."

Despite the headphones, he says he almost never listens to music while playing. He's too busy watching the other players. But there are occasions he'll get tired and put on some tunes to revive himself.

'Amazing cards' on Day 3

When Day 3 started, Gladstone ranked roughly number 175 of 380 — roughly average. His luck was about to change drastically.

"I just got dealt amazing cards right out of the gate," he said. "My first six hands were pocket aces, pocket aces, pocket jacks, pocket queens, pocket kings, pocket nines. Super strong, but it doesn't mean you're going to win."

He converted the first pair of aces into 60,000 or 70,000 chips. Not enough to make him the chip leader at his table, but close.

On the next hand, pocket aces again, Gladstone looked at his cards really quickly, put them down and announced to the table that he was feeling good and going to play the hand blind.

"Now if people want to buy that information that's their choice, but at the table it's war. You can say anything you want," he says, laughing. "And people do this all the time. And some people fall for it, some people don't fall for it. You're playing for money. This is poker. All is fair in love and war, right?

"What I'm trying to demonstrate is that I'm a crazy player. Some people think I'm a sucker in this situation and they want to take advantage of it."

At least one person at the table didn't fall for it, Gladstone remembers.

Gladstone opened with an outrageous amount, 100,000 chips, more than three times the normal opening bet for that situation. And one of his opponents bit, calling with a king and a jack suited.

Not a bad hand, generally, but considering the opening bet amount and the size of a man's chip stack, it was a foolish call. The shared cards didn't bail him out against the bullets.

Gladstone, now his table's chip leader, didn't play "goofy ball" after that. By 2 p.m., he was the chip leader for the entire tournament. By 4 p.m., he had a pile of roughly 1.4 million chips. Midnight passed and he was still raking chips into his ever-growing stack.

"All in all, I played a really solid game, I was dealt some good cards, I had to make some tough decisions, some tough lay-downs."

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Venetian Resort casino, 4:30 a.m. July 4, 2019 (cont.):

Final table of the Deep Stack tournament, four players left. Gladstone, the chip leader with 23 million in chips, is dealt an ace and king of diamonds. He's on the gun, meaning he's first to open, and he bets 4 million.

The two players to his left, one with about 9 million and the other 10 million, fold. His main challenger, the bearded Toronto fan with 21 million chips, shoves all-in. Is it a bluff? The Canadian has bluffed several times in the last couple of hours.

With the tournament on the line, Gladstone calls.

Blue Jays guy turns over his cards — ace of clubs and queen of hearts. Gladstone is elated.

"I am dominating this guy!" he says later. "The only way he beats me is (getting one or more of) three queens out of 52 cards. If nobody hits, I win. If a king comes up, I really win. Our aces cancel each other out. So he needs a queen — or by sheer luck a flush or a straight."

The dealer turns over the "flop," the three community cards in the second stage of betting, and Gladstone's elation instantly turns to despair.

Queen of clubs, queen of diamonds, four of diamonds — a terrible flop for Gladstone, but there still is hope. He needs a diamond in one of the two remaining community cards to make a flush, or else two kings.

He gets neither. The last two cards are a six and a deuce. He doesn't recall the suits, other than they weren't diamonds.

Down to this last million, Gladstone is dealt a 10 and an eight and busts out. He takes fourth place in the tournament, a $50,000 payout. Not shabby at all, but still, he was so close to winning it all.

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Did he make the right play?

Gladstone says he's asked professional players if he played "the hand that crushed me" correctly and most say he did.

But there is an argument that he shouldn't have played the hand.

After Gladstone busted out, the remaining players agreed to a "chip chop" — instead of playing out the remaining hands, they split the prize money, with the player in third place at the time taking home the lowest share of $102,000. Chip chops on the final table of high-stakes poker tournaments are common.

"So here's the argument why I shouldn't have played — that the payoff of implied odds effectively (made) that one hand a $50,000 play," he says. "Now I didn't know there was going to be a chip chop at that stage, but the value of what was distributed was the difference, by me just holding on instead of playing my hand, of $50,000."

That's what bothers him: He could have waited for one of the small-stack guys to bust the other out.

On the other hand, he was playing to win, not come in second or third.

"I was never folding my ace-king in this situation," he says.

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Mike Moffitt is an SFGATE Digital Reporter. Email: moffitt@sfgate.com. Twitter: @Mike_at_SFGate