Antonio Esfandiari on that $18m win and going back-to-back this summer: ‘Nothing will ever come close to that’

In 2012 Antonio Esfandiari won poker’s biggest prize at the Big One for One Drop. As the second $1 million tournament approaches, Howard Swains speaks to Esfandiari about how the $18m win changed his life

Antonio Esfandiari pads across a convention centre corridor and comes to rest in an ostentatious, oversized chair, the kind of ridiculous furniture that is scattered across the Atlantis Resort on Paradise Island in the Bahamas, home of the annual PokerStars Caribbean Adventure. He hoists his legs up on to a waist-high table, revealing a pair of white, towelling, hotel-room slippers. He then rocks back to settle the rest of his frame into the kind of comfort he has secured for his feet. 

All of a sudden, Esfandiari checks himself. ‘Are you okay if I put my feet there?’ he asks, genuinely fearful of having transgressed. In a vignette lasting all of ten seconds, Esfandiari exhibits the kind of devil-may-care confidence that made him one of the poker boom’s first clown princes, and then the new-found self-awareness that has, he goes on to explain, transformed him into a mature, content adult—and one of the best poker players in the world.

Esfandiari is 35-years-old and is, on paper at least, the highest money earner of all time in tournament poker. Although he readily admits the obvious – that the seven-figure buy-in to the 2012 Big One for One Drop was not all his own investment – he did the crushing of the event all by himself. It means that Esfandiari will be forever listed as the winner of poker’s first million dollar tourney and it was in his name alone that the $18.3 million winner’s cheque was made out.  

Party over 

Esfandiari is always an engaging and entertaining presence at the table

Esfandiari is always an engaging and entertaining presence at the table

Such a spectacular success would be the defining moment in any player’s career, but it goes double for someone whose previous major scores had tended to be overshadowed by time spent goofing around on television poker sets, or drowned in champagne in Las Vegas nightclubs. Esfandiari has enjoyed his recent vindication. He worked for it.

‘Pre One Drop, if you said, “Name the five most notable poker players,” it would not be me,’ Esfandiari says now, his slipper-clad feet given permission to remain. ‘It’s not that I was even mentioned. I’d been lurking around for a long time and I won a couple of tournaments early on in my career, and I got a lot of air time because I’m kind of talkative. But for a long time, people kind of wrote me off, and rightfully so, because all I did was party and hang out and I didn’t care about poker at all. I never focused and I just kind of lost my confidence a little bit.

‘When you don’t put yourself in the right mind-frame and physical condition to play poker and give yourself a chance to win, you’re not going to win. I was out partying every night and that’s not going to be a success story waiting to happen. So I got motivated about two years ago to start playing good again and to really focus. And as soon as I did that, I had some incredible results. I didn’t like being written off.’

Chief among those results, of course, was the jamboree in Vegas in the summer of 2012 for which he will always be remembered. Esfandiari was the last man standing from a field of 48 top pros and extravagant businessmen who flicked a collective middle finger to the post-Black Friday blues by stumping up a million bucks each to play cards. The tournament had the biggest buy-in of all time and the biggest first prize, but although it played out in an atmosphere of carefree, philanthropic friendliness (it made more than $6m for the One Drop charity,) Esfandiari was focused on the win. 

Watching the television broadcast back, it is never more obvious than when Esfandiari and Guy Laliberté, the billionaire founder of the Cirque du Soleil empire and the tournament’s organiser, got all their chips in on a coin-flip during the final table, Laliberté’s Queens against Esfandiari’s Ace-King. The players may have donned clown’s noses and embraced with genuine goodwill, but Esfandiari’s, ‘I need it more than you, Guy,’ has a distinctly beseeching tone. 

He now admits that had he lost heads-up to the British player Sam Trickett, the course of his life would have changed dramatically. ‘I’ve thought about that a lot,’ Esfandiari says. ‘I love Trickett, but I think that if you get so close to something so glorious and come in second, it’s going to hurt for the rest of your life. I don’t know if I would have truly ever gotten over it. I’m so glad I won that tournament because had I not, I would have been truly heartbroken.’ 

‘It’s like a presidential election,’ he adds. ‘It’s just you versus the other person, for super glory. You’re either the guy that almost did it, or did it. That’s a once in a lifetime opportunity. In presidential elections, the winner is the man. And the guy that almost won, was almost president, nobody cares.’

A bold prediction 

The Magician now has the kudos to go with his star status

The Magician now has the kudos to go with his star status

This summer, Esfandiari will have the chance to stand for a second term as poker’s president when the One Drop returns to the World Series schedule. (He came fourth in the scaled down renewal in 2013, won by Tony Gregg, which required ‘only’ $111,111 to play.) Esfandiari will, of course, be in a field he predicts will have swelled to about 56 players and be hyped even more intensely than before. However only he has the chance for a unique double. ‘This will be the true back-to-back,’ he says. ‘When I win this tournament, how is anyone ever going to compete with that? I don’t mean to sound egotistical, but that would be my legacy. For sure. Nothing will ever come close to that, and I’m the only person that can do it. I’m about as motivated as it gets.’

Esfandiari’s insistence that he ‘will’ win the tournament is not uttered accidentally. In his ESPN interview ahead of the One Drop final table, Esfandiari responded to Kara Scott’s question of what he would do if he won the event with, ‘First of all I have to correct you, there’s no “if”, there’s “when”.’ It’s a line I heard amid our attempts to schedule a meeting during the whirlwind that is the PCA. Esfandiari could guarantee his availability for PokerPlayer only in principal, with this habit of winning poker tournaments usually getting in the way. ‘As soon as I win this tournament I am all yours,’ he wrote in an email at the end of the first day of the $100,000 Super High Roller event. ‘IF they HAPPEN to bust me…(not happening) then I’m all yours.’ The capitalisation is his.

He ended up finishing fourth in the Super High Roller, his first event of 2014, playing long into the night for two days before losing a flip to Vanessa Selbst and banking close to $600,000. He then immediately started the $10,000 main event, lasting again until Day 3 and ensuring he kicked off the new year with a two-for-two cashing average. We finally got together after the $25,000 ‘regular’ High Roller event didn’t pan out as expected, freeing Esfandiari for a day, to watch the
San Francisco 49ers in the NFL play-offs and record another round of interviews for the PCA shows to be aired sometime this year. ‘I haven’t been outside, by the pool
or in the ocean one time, which is super tilting,’ he says of his trip. ‘I want to go check out the ocean.’

Leading the pack 

Positive thinking, and ‘checking out the ocean’, is a significant part of Esfandiari’s recent reinvention. Although he does not reference any organisation by name during our conversation, Esfandiari is well known as one of a number of high-profile poker professionals to enrol in a so-called leadership university in Las Vegas that offers intensive, and sometimes controversial, personal development programs. (Daniel Negreanu is another vocal advocate.) 

Esfandiari said he resisted signing up at first, but now describes an ‘incredibly rewarding and refreshing’ experience that helped him address some personal issues that had lain unresolved since his childhood. He says he learned to confront emotions, he learned to cry and he learned to accept ‘I am who I am.’ It moved him into a more responsible phase of his life. ‘I think we can all grow no matter who you are,’ he says. ‘It hit me like a massive force. All of a sudden I got to deal with so many different things I didn’t even know were an issue for me.’

Esfandiari’s young life cultivated both sides of his character: the showman and the focused individual with a point to prove. Born in Iran in 1978, his family relocated to San Jose, California when he was 9-years-old. However his mother returned to Tehran soon after, apparently abandoning her two sons, and leaving Esfandiari with some deep scars that took more than 15 years to heal. ‘I thought that my mom had left me,’ he says. ‘I was a kid, it hurt me and I cried lot… I had all these insecurities that I’d built up. I hated being alone. I was very insecure. Even though I was a very confident person, deep, deep down there were certain things that I was very insecure about.’ Esfandiari and his mother, who now lives in Paris, have since been reunited and are very close.

Originally, it was magic that offered the young Esfandiari the opportunity not only to become the centre of attention, but also to display his card skills. Poker followed when he was 19, and he soon found himself perfectly positioned to make the most of the boom of the mid-2000s, when the producers of television poker shows were seeking young, good-looking folk with a natural table-manner to become the superstars of the new era of the game.

It helped, of course, if they could play a bit and Esfandiari ticked all the boxes. He won the WPT LA Poker Classic in February 2004, a matter of months after Chris Moneymaker won the World Series, and then his first bracelet back in Vegas that summer. Esfandiari was a regular booking on all of the most prominent shows on both sides of the Atlantic, and he rolled along with the momentum. He wrote magazine columns describing a hedonistic lifestyle, jetted across the world in search of a party and was romantically linked to numerous women.

The Ultimate choice 

Esfandiari has signed a deal with Ultimate Poker in the States

Esfandiari has signed a deal with Ultimate Poker in the States

His obvious marketability also ensured a steady stream of sponsorship opportunities, however his newfound financial freedom has recently afforded him the luxury of picking and choosing endorsement deals based on factors other than the bottom line. In April last year Esfandiari signed a deal with the Nevada-based Ultimate Poker to be its first global ambassador.

‘I could have gone with different sites to make probably more money on a regular basis, but I’m not about that,’ he says. ‘I told them I want to be part of the process and I want to watch the company grow. And some day when the company is worth a ton of money, then I’ll really cash out. I’m going for the long-term play.’ Esfandiari says that his friendship with Tom Breitling, the 44-year-old founder of the site, was decisive. ‘I look up to him in an entrepreneurial sense. He’s a very, very sharp guy. When he says, “Look, I’m starting up a poker site with the Fertitta brothers, who also own UFC,” it’s kind of hard to say no.’ 

Esfandiari is a UFC fan, likening its showpiece bouts to heads-up duels in poker, with everything on the line. ’It’s mano-a-mano and I just love that,’ he says. However, his deal with Ultimate is mutually beneficial, allowing him to play when he is at home (Ultimate is one of the first sites to launch post-Black Friday in the United States) and to fulfil his own modest entrepreneurial ideals. ’They bring me up to speed with a lot of things and if there’s a big marketing decision – a ‘should we do this, or should we do that?’ – they run it by me,’ he says. ‘They take my opinion into account. But I don’t know the first thing about running a company. I’m a one-man operation. These guys are great at what they do and I trust them, obviously, to do whatever they need to do.’

Living the dream 

Despite the success poker has brought Esfandiari, and the impression he can often emit of being one of the game’s secret scholarly nerds (perhaps it is the glasses), his work-life balance these days is still deliberately skewed towards ‘life’. ‘If you knew how much poker I played or studied or spent time on in the last ten years, you would be absolutely shocked,’ he says. ‘I almost never play poker. I go to these big tournaments, but all the downtime in the middle I don’t even play poker. I’m just hanging out, enjoying my life, travelling, you know. Wine tasting…’

He says he plays perhaps one or two hours a day at the low-stakes tables on Ultimate Poker when he is home in Las Vegas, but is only an infrequent visitor to the Aria card room, whose name he also wears on his chest. ‘I really don’t play live that much,’ he says. ‘The Aria game is a game with more businessmen than pros, and I respect that. I’m not the kind of guy who’s just going to show up and sit down if I’m not invited…Anybody can play in those games and a lot of pros go and put their name on the list and jump in. But sometimes they want to play just the business guys and when that’s the case I think it’s rude for the professional to go in when they’re not really wanted.’

Esfandiari’s current tournament diet consists almost entirely of the high buy-in events, the High Rollers and Super High Rollers that have created a kind of poker premier league for the elite. It took Esfandiari ten and a half years to accumulate his $4.9m lifetime cashes before the One Drop but only 18 months since then to record another $3m, the clear result of playing much bigger. 

But the sharpness and motivation remain both on and off the tables and he reels off a never-ending list of titles that still elude him, summarised with: ‘I just want to win more stuff.’ Yet for all the magazine covers, appearances on Howard Stern, multi-million dollar pay-days and potential re-election as poker’s unofficial president, there also now exists a more profound, more grounded version of Antonio Esfandiari. ‘It’s not that I don’t want to be a superstar,’ he says. ‘But would I want Daniel’s role, as far as being an ambassador, the face of poker, someone that’s so involved with the way things are, tournament rules and all this other stuff? No. I would not want that. I just want to get in, do my thing, play poker and go live my life. I play poker to live my life, I don’t live my life to play poker.’

The magician’s greatest moments

Esfandiari out-bluffs Einhorn

Esfandiari played solid poker and won flips on his way to winning the first Big One for One Drop and $18.3 million, but The Magician also knew how to pounce on the weaknesses of the amateurs in the field. 

Chip secrets with Antonio Esfandiari

Okay, maybe not his finest moment, but certainly one of the funniest. The young Esfandiari gives a startlingly earnest tutorial into how to riffle chips, cut cards and, er, look kind of awkward in front of a camera. 

Politics gives me wood

One of Esfandiari’s greatest calls: to a sex hotline, where he turns the tables on the operator and quizzes her on politics, geography and current affairs. Warning: also features Howard Lederer.

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