Drake Revealed $8 Million In Sports Betting Losses
“I love losers,” Steve Cyr, the flamboyant Las Vegas casino host, once told me.
This statement was not made in confidence. In fact, he was hoping that I would quote him in a story. Never mind that such candor runs counter to common thinking.
Most hosts push out the theory that casinos don’t care if their players win. They just want them to put in the time and play – maybe Cyr was onto something.
These days, it seems as if we embrace our losers. As was recently written in Card Player, the superstar rapper Drake went out of his way to reveal some $8 million in sports-betting deficits.
“Gotta share the other side of gambling … Losses are so fried right now,” he posted to Instagram.
Maybe people love to know that even the world’s sharpest, most adored among us are capable of being hosed by casinos – just like we all are.
While reporting my book Advantage Players, I had a steak dinner at Peter Luger with the uber advantage player James Grosjean. He was integral in the multi-million-dollar rampage that Don Johnson (the high-stakes gambler, not the actor) ran through casino blackjack games.
Vegas Matt Goes Viral For Big Bets
Though Grosjean hates losing, one of the things he admired about Johnson was the way he handled the downside.
“Don Johnson has a stomach of steel,” Grosjean told me. “He can lose a million-dollars and get up from the table with just one question: ‘Where are we eating tonight?’”
Pros Hate Talking About Losing
World class gamblers were not always so forthcoming. In preparing for an interview on a podcast about gambling writers and their favorite books, I have been re-reading the fantastic Fast Company by Jon Bradshaw.
It was reported in the 1970s, at a time when serious journalists (and Bradshaw was one for sure) did not flock to the World Series of Poker. He did, however, and he got great stuff about winning.
In reading profiles of people like Puggy Pearson, Johnny Moss, and the famous pool hustler Minnesota Fats, one walked away with the realization that losing (which is a fact of life for even the most successful gamblers) was the last thing they wanted to acknowledge.
Moss pretty much summed it up when he told Bradshaw, “Losin’s not very interesting. And, besides, I know a lot more about winnin’, playin’ and winnin’. It’s what I do best. It’s all I want to do.”
But I’m glad that people who gamble publicly are more willing to show the ups and downs of their worlds.
Big Views For Big Losses
The greatest example of this is Matt “Vegas Matt” Morrow. He started out as a wealthy guy who retired to Las Vegas with a decent nest egg. He loved gambling, enjoyed being in casinos, relished the comps. He allowed himself a certain amount to lose each month.
Like most recreational gamblers, Vegas Matt was not disappointed by the negative outcomes (he was budgeted for losing). However, after he hit an elusive royal flush on a video poker machine, his son posted the big win to a freshly launched TikTok account. They were shocked that it got a load of views.
The next night, they tried to replicate the big-win result and failed. Not letting it get them down, Vegas Matt and his son posted that outcome to TikTok.
The loser got more hits than the winner. People preferred to see his losses. A lightbulb went off, and, as Vegas Matt told me, “We said, ‘Why don’t we keep doing this?’”
From there, a brilliant idea was born. Right now, Vegas Matt gambles daily. His son captures it all on iPhone video and he has a crew of fellow gamblers with him. Loaded with commentary and enthusiasm for high-stakes risk, the videos drop onto YouTube where the Vegas Matt channel has some 1.2-million subscribers. They ride along with him as he wins and loses.
Vegas Matt can blow a bundle each year and way more than make up for it with revenues from YouTube.
By showing the beatings – a couple weeks ago, I was with him and his crew, in the Venetian and Resorts World.
I watched them speedily drop some $60,000. As he bit into a free chocolate chip cookie and dryly commented on the tastiness of his $60,000 confection, it became clear why Vegas Matt is so relatable and compelling.
“I get bummed about the losses,” Matt told me. “My emotions are always on my sleeve and the people love it.”
Michael Kaplan is a journalist based in New York City. He is the author of six books including The Advantage Players, and has worked for publications that include Wired, GQ and the New York Post. He has written extensively on technology, gambling, and business — with a particular interest in spots where all three intersect. His article on Kelly “Baccarat Machine” Sun and Phil Ivey is currently in development as a feature film.
*Photos – Twitter/Vegas Matt
