LAS VEGAS — The curious kid sidled up to the table on which her dad and his pals were playing poker, captivated by the cards and the money and the action—especially the action.
Born and raised in Manhattan, Kansas, Kelly Stewart clutched a purple-felt Crown Royal bag containing her life savings, about 70 bucks, all change. John Stewart told his 11-year-old daughter to sit still, they’d finish and some would remain to teach her Texas Hold’em.
“Of course, we clipped her,” says John, 74, now a rancher in Montana.
Today, Kelly is a one-woman gang, a petite dark-blonde dynamo, the most-renowned female in Las Vegas sports betting whose signature parlay — The Hottie Three-Way, she’d dub it — would alter her life.
Twenty-five years ago, though, she begged for her money back. John shook his head. No, he said, now you’re broke. You’re not getting it back because that’s the way the game is played. He kept the purple bag, too.
“Wanted to teach her a lesson,” he said. “I tried explaining it to her, but it didn’t stick. ‘Kell’ was a different child. I think it just made her want to play harder.”
On a recent visit to Montana, his friends and her wound up gambling, as usual, in a bar. The game was Ship, Captain and Crew, involving five dice. Six is the ship, five the captain, four the crew. Three rolls. Obtain those first three, the other two dice constitute the cargo.
Largest cargo figure of the round wins.
Kelly clipped them for 700 bucks.
“She worked them over,” John says laughing. “I was sitting there drinking a beer, watching her with the rest of the bunch. They’re waiting for her to come back. They all think it’s funny, and it kinda was.
“They were writing a lot of checks.”
CAN’T DO EYEBALLS
To comprehend how a Kansas tomboy has soared in such a male-dominated environment, it helps to tap her rancher father and mother, who works in human resources, for insight. A Kansas State-crazed aunt also had a major assist.
John Stewart’s one tour in Vietnam started with Operation Starlite, the first major offensive by a purely U.S. military unit, on the Van Tuong Peninsula in August 1965.
He and the rest of the 7th Marine Regiment, plus elements from other battalions, drove the enemy into Nho Na Bay. Two destroyers and a cruiser opened fire, shaking the earth. “The navy killed everything that tried to swim away,” says John.
He won’t discuss his nine other missions within that 12 months. Kelly has been a bulldog in battling Veterans Administration bureaucracy on John’s behalf as he deals with Agent Orange side effects.
Upon landing in San Francisco, where he’d finish his hitch working security at Naval Station Treasure Island, protestors spit in John’s face and called him a baby killer, igniting a melee.
“It got way out of hand,” he said. Instead of taking him downtown, police who were former Marines instead delivered him to the island gate.
“When I was younger I didn’t let nobody bother me. I was 5-foot-8, 185, zero tolerance. If you did something to me there’s a good chance that I’d whoop the hell outta you.”
As a civilian, he worked for a high-ranking friend in Quantico, Virginia, doing undercover reconnaissance at army bases throughout the Midwest.
“There’s a lot of fraud, waste and abuse in the government,” says John, without elaborating. It kept him near home, enabling him to teach Kelly how to bait a hook, gut a fish, fire shotguns and field-dress deer. Pheasant and rabbits also entered her crosshairs.
“She’s a good shot,” he said. “That kid’s a shooter.”
Kelly was 5 when she caught her first walleye in Milford Lake, 20 miles west of Manhattan, Kansas. At a bar, over a hamburger and Coke, she dangled the fish on a stringer before his friends.
Her prized catch is the 98-pound halibut that took an hour to wrestle into the boat in the Gulf of Alaska.
“Reeled it in in three hundred feet of water,” she said. “So crazy, my arm was about to fall off. It was huge, floppin’ around. I hit it over the head with a baton and an eyeball pops out. I can’t do eyeballs. Wow.”
When John and Susan divorced in 1992, Susan’s sister Helen Hayes and her husband Billy Graham (no relation to the evangelist) had already been taking Kelly to Kansas State basketball and football games, and spirited tailgates.
“They and their friends just inundated her with sports and camaraderie and adult conversation,” Susan said. “Kelly was their adopted child.”
Kelly would ponder attending the University of Arizona or San Diego State, but Susan — unable to fund out-of-state tuition — hoped Kansas State’s pull on her would decide that issue.
It did. Kelly majored in business, minored in fun. She had attended Manhattan High School, but she and her friends left the 2000 Class 6A title game in Lawrence at halftime — Darren Sproles and Olathe North, who would win 42-7, were having their way with Manhattan.
When Sproles selected Kansas State, she rejoiced, knowing the Wildcats were getting a spitfire. They didn’t cross paths, since he was serious about football and studies.
Her mother makes a corollary between Sproles, a versatile 5-6 back who would amass more than 20,000 all-purpose yards and 71 touchdowns in 14 NFL seasons, and Kelly.
“In heels, I’m literally taller than he is,” Kelly said. “When I found out he was going to Kansas State I was super happy, but I think Darren has overcome a lot more obstacles in life than I did. I’ve been pretty lucky.”
LOOK OUT VEGAS
Stewart had a post-graduate interview, through her aunt, with an insurance firm. She informed her dad of its lowball fifty-grand salary offer, which stumped him because, in his world, that’s damn good money.
Not hers. A fruitless internship with the Denver Broncos made her pivot, joining a friend who was moving to Vegas. She eyeballed making six figures, working bottle service in the ritziest clubs on the Strip.
One NFL player embarrassed himself when he berated her for having not listened to his instructions — in fact, another server had requested Kelly’s assistance, and something got lost in an exchange.
“The rudest ever,” Stewart said. “He backhanded a drink out of my hand and was screaming at my face. I’m like, ‘You dumb shit, I’m the waitress at the next table. Your waitress asked me to help. So, no you [bleeping] didn’t tell me.’ It was bad.”
Several friends bet sports, again sparking her curiosity. To learn the lingo, she would stroll to the window to make their bets for them. She’d digest point-spread movements, sucker lines, half-point hooks that can crush or reward.
The three-team money-line parlay she hit on Sept. 22, 2012 drew the attention of Matt Youmans, then writing about sports wagering for the Las Vegas Review-Journal and talking about the business on the radio.
Oregon State, Rutgers and Kansas State were all road underdogs. She had eschewed taking the points, in each case, for a sweeter combined payday if all won outright. The Beavers beat UCLA 27-20, and the Scarlet Knights (35-26 over Arkansas) and Wildcats (24-19 over Oklahoma) completed the hat trick.
A hundred bucks became eight grand. In two months, she’d turn 29. To Susan Stewart, that was prophetic.
“I had asked her, ‘Please be gone from Vegas by the time you’re 30.’ She started having success. She has found her niche, but it did involve a certain amount of luck.”
Kelly christening her wheelhouse action, The Hottie Three-Way, shows she knows the arena, what sells, allure. Her avatar on Twitter, where she promoted her picks, was a photo of her in a skimpy purple K-State uniform wearing eyeblack.
Youmans profiled her in his column, had her guest on his radio show.
The legend and lore of Kelly in Vegas had taken off.
RIDING A WAVE
Kenny White, then COO of the Don Best odds service, hired her when she excelled — in delivery, manner, and sports and sports-betting terminology — in a video tryout. For two years, she helped produce exceptional content.
“Her eagerness to learn more about power ratings, injuries and trends was amazing,” White said. “She soaked it all up and continues to climb to the top of the sports-betting mountain.”
Stewart also participated in Review-Journal videos with Youmans and Todd Dewey. This season, for the sixth time, she is part of an elite panel for that paper’s weekly college football pick’em contest.
“She’s street-smart and book-smart, fun and tough,” Dewey said. “And Kelly Stewart doesn’t take anything from anyone.”
Showtime featured her in its four-part “Action” sports-betting documentary in early 2019. She is a media liaison/producer/host for WagerTalk and a betting insider for Bleacher Report.
Via Time Warner, BR’s parent company which also owns Turner Sports, she calls NBA games in a live stream with two others from a betting perspective, an idea hatched by NBA commissioner Adam Silver.
“The NBA is the best example for live betting,” she says, “because the runs are so incredible.”
She partners with Brett Siedlecki, her boyfriend of five years who is well-versed in sports wagering, in operating the popular Kelly in Vegas proxy service. Non-Nevada residents hire them to submit weekly picks to high-dollar Circa and Westgate SuperBook football contests.
WagerTalk veteran Ralph Michaels says her work ethic is nonpareil, that she has succeeded by knowing football, making strong statements and backing them up against anyone. He admits — as does Stewart — that she capitalizes on certain assets.
“But it also must be pointed out that she spends tremendous time in the gym with a trainer, and dieting,” says Michaels, “to ensure she looks and feels her best, performing at peak level.”
Twice a week, she partakes in a podcast with John Murray, the director of race and sports operations at the Westgate SuperBook. While juggling those responsibilities, she crunches numbers and taps a bottomless reservoir of resources to earmark wagers.
“Her popularity is very high right now,” Murray said. She’s taking advantage of it, and I say good for her.”
Someone stopped her in the SuperBook recently and applauded her consistency on every platform in stressing the importance of money management. Go broke a couple of times, she responded, and you’ll be better about it, too.
He grinned, but she meant it. She discusses that golden rule often with Gianni “The Greek Gambler” and Marco D’Angelo on WagerTalk’s “Bet On It” videos.
The mid 20-year-old males with whom she works at Bleacher Report tend to roll their eyes when she shifts into that spiel, but that’s the precise audience that requires such discipline.
“You lose ten grand in a week and you’ve only got fifty-six hundred [in the bank]?” she said. “That’s not good. ‘How did I get there?’ Well, you went from a nickel [$500] player to all of a sudden you’re betting two dimes [$2,000] on the second half of a game? You’ll go broke quickly.
“I had to learn the hard way.”
THE IRISH IN HER
In February 1976, Georgie Fairbanks became the first female to “sit box” at a craps table, managing its operations on the Strip at the original MGM Grand. She took static from players and colleagues alike but it didn’t affect her.
“I was the only girl in the whole dice pit, and I loved it,” Fairbanks, 70, said. “First, I was a tomboy. Second, a flirt. I was in heaven. I knew I was better than most of them. Had to put up with a lot of [expletive], but they couldn’t intimidate me. I didn’t consider myself tough, it was just easy to laugh.
“That’s probably how Kelly feels, too.”
The two have never met.
“I’m sure Georgie went through a lot more [expletive] than I ever did,” says Stewart, who knows women who were the first females in police departments. That, to her, is breaking a significant barrier.
“For sure, you can laugh about things . . . but I’ve been very quick to put someone in their place if they’re rude. I’ve had to learn to not do so. Does that mean my skin is getting thicker or I’m being more tolerant?”
According to John Stewart, it’s simple with Kelly.
“Treat her with respect and be decent,” he said. “But if you upset her, you bring out the Irish in her right now.”
She once said she knows football better than Fox’s Erin Andrews and is better looking than ESPN’s Rachel Nichols. To be fair, though, that was eight years ago.
Keyboard adversaries who get a “Bro” from her should take it as a warning shot across the bow. She tries practicing discernment, with a little help from Siedlecki, and aims to keep evolving.
“I can be a little brash or abrasive, but I think most men are okay with that,” Stewart said. “The ones who are timid or shy, for sure it’s, ‘Holy hell, who is this broad?’ Nobody wants to be emasculated.
“As crazy as I am, I still need to remind myself, ‘Hey, you’re a 5-foot-3, 110-pound woman . . . you can’t just think you’re this giant pit bull.’ ”
That strong personality first attracted her to Siedlecki. He still laughs at parties when she mingles with the males, discussing coaches, plays and point spreads, picks at the charcuterie boards surrounded by females, then returns to the game on the big screen to banter with the boys.
When she returned home the night of Sept. 7, she had just finished spending four days inking 77 proxy clients, over 30 total hours, to the two Circa football contests at the Golden Gate.
Siedlecki surprised her with a two-hour session with a professional masseuse, custom table and all. Afterward, she found four voicemails and 81 text messages on her cellphone.
Many texts were of the group variety, involving an Over wager they’d made on that night’s Clippers game. It ended 113-107—some had 219, others pushed at 220, a few had 220.5. She worked for a few more hours.
“I’m not sure where she gets her energy,” Siedlecki, 32, said. He’s a morning person, she’s a certified night owl. “I think it’s a blessing and a curse for her.”
He long ago envisioned the industry becoming more and more corporate, so he advised treating social media as office space requiring constant tact.
“Pressing the Block button,” he says, “is much easier than giving some coward the satisfaction of a response and potentially saying something she may regret.”
The Showtime exposure led her to a talent agency, and subsequent interviews with major TV networks. More are on the horizon. She will not be a cutesy emcee, asking questions — she wants to be an expert, fielding those inquiries.
And on Feb. 12, 2019, her lore hit another level when ESPN SportsCenter highlighted a Hottie Three-Way that failed. LSU and Penn State had won as college hoops underdogs, but Louisville frittered away a 23-point lead, in less than 10 minutes, at home to Duke.
Her $100 did not become $7,668.31. Such exposure on a losing ticket was testament to sports betting’s popularity and Stewart’s fame.
“Yeah, that’s awesome. But it was more like, ‘Kiss my a—, SportsCenter. You guys now want to put me on there?’ Poured salt in the wound. I thought, Next time I hit one of those it’ll be 2027.”
She nailed a college football Hottie Three-Way last fall, and two in the NFL.
WELL, DON’T BET HER
Susan Stewart is most proud that Kelly is mentoring other young women, not necessarily to take business away from her daughter but to help them navigate a savage industry.
In the summer of 2019, Kelly declined an invitation to fill a vacant block on a radio show but recommended a new colleague, who visited the studio for the session.
The 27-year-old Minty Bets, her professional alias, had been betting on sports since 2014 and had just joined WagerTalk. She knew of Stewart, believed her strong personality might be intimidating, but instead met a kind soul who has become a dear friend.
Stewart has pressed Bets to become comfortable with the uncomfortable, to create a brand name and ceaselessly expand on it. Just watching Stewart, who is always on the move, inspires the understudy.
“If it wasn’t for Kelly I definitely wouldn’t be in the position I am today in sports-betting media,” Bets said. “Her ability to always stay working, to never have lazy days, is beyond me. She sets goals, then skips over them to achieve even higher goals.”
His daughter hasn’t really surprised John Stewart, who permanently relocated to Montana in 2006.
“Way back in high school, she was betting college football with my friends. So she knew what the hell she was doing.”
Did she win more often than she lost?
“She always had a pocketful of money. Those guys . . . I’d just laugh and say, ‘Well, don’t bet her.’ Everybody here is proud of her. You don’t run across a Kelly Stewart every day. When she rolls into Grass Range, Montana, these cowboys go crazy.”
They inquire, When is Kell comin’? She’ll be here for four days? We’ve got to take her prairie-dog huntin’, and we got to do this and we got to do that, then we gotta play cards.
“Well,” John tells them, “as soon as she gets here.”