Why you should care

Because gambling legalization is creating a new kind of media star.

Against The Spread: This OZY Series Probes Sports Gambling's Future.Against The Spread: This OZY Series Probes Sports Gambling's Future.

Kelly Stewart sits inside her car, moments away from entering the new home that she’s about to purchase in suburban Las Vegas. It’s her first, and she’s thrilled to get inside to sign the papers. First, though, Stewart has to finish telling her story about winning thousands off Pope Francis.

Back in March 2013, Stewart — a professional sports handicapper, WagerTalk’s director of media relations and the new gambling expert at Bleacher Report — was five years away from making betting her full-time career. But when a friend and Notre Dame University graduate with “connections” inside the Catholic Church found out that Stewart’s bookie took bets on the papal conclave, and that then-Cardinal Jorge Bergoglio of Argentina was a 14:1 long shot, he was adamant that they place a bet together. The pair wagered $300 and when white smoke emerged from the Vatican their hefty payout followed.

It was only fair, Stewart concluded, that they give 10 percent back to the church, even though she’s no longer a practicing Catholic. “This past St. Patrick’s Day, I had to ask my mom to break a $100 bill so I could run inside and pay my debt.”

I’m not here to be the pretty host. I want to be the best analyst there is.

Kelly Stewart

That’s the code for Stewart: Gather intel from anywhere, pick the undervalued underdog and repay favors. To the uninformed, it might appear that the former nightclub cocktail waitress is enjoying overnight success, popping up on televisions to make bets with Charles Barkley. But after the better part of a decade, Stewart has turned her hobby into a sustainable, and soon-to-be common, career.

Last May’s Supreme Court decision to overturn a law prohibiting sports betting in states other than Nevada has opened the floodgates. The once-taboo practice becomes trendier by the day and, suddenly, companies like Turner Sports — which owns TNT and Bleacher Report — are hiring gambling analysts who are more palatable than the stereotypical handicapper waving his cigar in the air and screaming inside the sportsbook.

“Kelly’s personality connects with who our audience is and what they respond to,” says Sam Toles, chief content officer at Bleacher Report. “We needed someone fresh to introduce this world to a new audience.”

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Former nightclub cocktail waitress Kelly Stewart is making a name for herself in sports betting.

Source Kelly Stewart

The way Chad Millman, head of media at the gambling-focused Action Network, sees it, mainstream acceptance has reopened the way we think about gamblers. “The average fan has access to enough data to become educated, and we’re seeing demand for more information. That creates opportunities,” he says.

Enter Stewart. Sure, she has been caught screaming in the sportsbook on occasion, but she cuts a far different figure from most in the industry. Finally, the distinction that presented early hurdles in a male-dominated field is seen as a positive. “I feel like I’ve always been able to find an edge,” says Stewart. “But, early on, people tried to discredit me. As long as you’re winning, eventually they’re forced to pay attention.”

Not even the best handicappers are right all the time. The key is being able to prove that your guess is an educated one, ideally supported by unique information. In sports betting, a successful win rate is anything over 52.4 percent, just enough to ensure you’re not losing money. The industry is rife with gamblers who claim absurdly high win rates, with many such characters — known as touts — selling their picks.

“I never wanted to be a tout,” says Stewart, who was making six figures waitressing in nightclubs and had no interest in working more. But fellow handicappers and frequent collaborators Todd Fuhrman and Kenny White persuaded Stewart to give it a try. “I was already putting in all of the work, so why not make extra money selling picks?” she says.

In 2014 and 2015, a scantily clad Stewart sold weekly underdog picks to clients via her “Hottie3Some” videos. Her sex appeal caught eyeballs; her college football success earned credibility on the Strip. “When you’re hot, you’re making money and life is good,” says Stewart. “But then I had a really mediocre college football season, and it pretty much dried up.”

Aside from a few personal clients from the old days, Stewart no longer sells her picks. After being featured in the recent Showtime documentary series Action, she’s had plenty of requests to reconsider. Instead, she’s focused on her own gambling and media ventures.

From contributions at CBS Sports to her new appointment at Bleacher Report, she’s hitting the mainstream after years of work to establish her credibility. That wasn’t always easy. Early on, Stewart often heard other Las Vegas handicappers discrediting her as a fad. Meanwhile, most major television networks shied away prior to federal sports betting legalization. “I’m not here to be the pretty host,” she says. “I want to be the best analyst there is.”

Stewart credits her father for showing her the ropes growing up in Kansas. John Stewart enjoyed making silly bets with his young daughter for whatever was in her piggy bank, and he was known to enjoy social games of cards and keno. Dad’s bets left an impression. “That’s how he quit smoking,” says Stewart. “In 1987, a friend bet him $1,000 he couldn’t, and he was done.”

For his daughter’s 21st birthday, John took Kelly to a casino to learn to play blackjack. But he made one thing clear: Always look for an edge. Table games and the slot machines are where edge goes to die. When Stewart moved to Las Vegas, four days after graduating from Kansas State University in 2007, she soon learned that too much time on the tables would blow through her nightclub earnings. “But a friend of mine noticed that I had a knack for picking games, even though I didn’t know much about the spreads,” she says.

Her breakout came in 2012 when she placed a $100 money line parlay at the Bellagio for three college football underdogs to win. The bet won $8,452 and earned her a weekly spot on ESPN Radio and a gambling column in the Las Vegas Review-Journal. It also showed what Stewart believes is her biggest asset as a handicapper.

“I’m a situational bettor,” says Stewart. “I’m looking for underdogs that can win outright. The algorithm-based handicappers don’t make those bets, because the math says that those teams don’t have a chance to win.” Stewart uses trends and data at her disposal to choose her spots, and the rare money line parlay win is a tasty added bonus. Stewart specializes in college football — where unpredictability is higher and upsets more common than the NFL — with college basketball a close second.

Back in February, Stewart appeared to hit the college hoops jackpot with a three-game parlay with underdogs whom Vegas all had at greater than a 3:1 longshot. After LSU and Penn State won, then Louisville went up 23 points on Duke, Stewart was nine minutes away from a $7,668 payday. “I was already planning my trip to Hawaii,” she says. But Duke pulled off the stunning comeback to win, and Stewart’s ticket was worthless.

There was no white smoke that day, but luckily Stewart had placed large single-game bets on the other winners. It doesn’t hurt that she has a few more checks coming in these days.

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