Bill Krackomberger not only gives gamblers winners but also some hard-learned lessons

Bet on it: The Vegas fixture isn’t shy about talking about the dangerous side of betting.

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Bill Krackomberger

Bill Krackomberger at South Point Casino

Rob Miech/Sun-Times

LAS VEGAS — Bill Krackomberger got in too deep with a bookie in New Jersey. He chased sports-wagering losses. Kept losing. He owed $10,000 to the guy, who threatened to break his legs.

Krackomberger was 15 years old.

“I was scared,” he says. “He was no one to mess with.”

His father’s boss loaned the money to Bill, who’d return it in installments. Today, the 53-year-old professional bettor known as Krackman is a familiar brand.

He starred in Showtime’s 2019 four-part “Action” documentary and is a regular guest on the Vegas Stats & Information Network (VSiN).

A trademark derby, dark shades and KW mark the gold hexagonal logo on his KrackWins website, where his picks can be purchased. houses his Wise Kracks podcast.

The Bronx-born Krack is sought for insight on an industry that set a record with $1 billion in monthly business in New Jersey in September and whose national monthly handle is expected to clear $5 billion, thanks to Illinois, for the first time.

He unabashedly says what many don’t want to hear.

Betting on sports can be dangerous.

“You won’t get a lot of people in this space to talk about this, either, because they might be a spokesman for a site,” says Krack. “I am, too. I don’t care. It means more to me to have safe, responsible gambling.

“I wish it were pushed even more. I push it and people freak out. ‘Oh, my God. He’s talking anti-gambling, anti-sports betting!’ I’m just talking realism. I know what I went through as a kid. I still fight demons.”


For 50 cents an hour, 9-year-old Krack first cut pies into slices at Pizza Villa, still run by an aunt and uncle on the Jersey Shore in Keansburg, N.J.

He’d oversee the basketball rims, milk-jug stands and dartboards on the boardwalk arcade. At night, patrons turned those games of chance into gambling mechanisms.

His father, lured to Monmouth Park and Meadowlands Racetrack by his wife’s relatives, took Bill to the horses when he was 10. At 11, cousin Anthony taught him blackjack, how to count cards and, most importantly, to note remaining aces.

“A rite of passage in the Bronx, from grade school on . . . all the knock-around guys gambled in after-hours social clubs. My dad, by the way, was a stone-cold sucker. Like everyone else, he didn’t know any better.

“I didn’t realize [horse tracks] held 25 percent. I know now. Guys just wanted action, nothing else. I grew up a sucker.”

At 15, the family moved to Keansburg. His parents couldn’t send him to college. Krack knocks twice on our table in a South Point lounge. Thank God, he says, because he’d learn invaluable street lessons.

He’d peddle cemetery plots and radio ads, wash cars in the winter.

“I’d get my hands dirty. Probably had 40 jobs.”

Frank, a professional bettor in Atlantic City, taught him advantage gambling, on slots and with sports. Says Krack, “It just took off. Man, it worked out big time.”

It’s 9 a.m. He exits VSiN’s glass-walled studio, in the South Point, where he did his weekly stint with “A Numbers Game” host Gill Alexander.

“My hour with Bill is unlike anything else you’ll hear in sports-betting media,” says Alexander, “precisely because we are unscripted, no topic off-limits.”

In eight hours, Green Bay plays a Thursday night game in Arizona.

Money has swamped the 7-0 Cardinals, inflating the line because many Packers receivers are shelved. The bookmaker also knows that, says Krack. Bet on Arizona, he says, and you’re going to pay a tax.

He mostly avoids the NFL, but he knows this game’s advantage play.

“You want to be on the bookmaker side. Think what [the public] is betting. Long term, you want to be on the other side of that.”

Green Bay wins 24-21.


Sharp syndicate contacts, whom he met during Vegas visits, further polished Krack’s acumen. He and wife Kelly, who moved here in 2004, reside high above the fray in Turnberry Towers.

He flies to Colorado to nab a $7,500 sign-up bonus at a new sportsbook. He leaves with five figures. Most weekends, he has six figures in play.

He casually mentions having wagered, the previous night, $5,500 on Vanderbilt. Two days later, 16½-point-underdog Vandy covers in a 37-28 defeat to Missouri.

Demons appeared a while ago. Krack pumped $5,000 into a slot machine. Instead of cutting his losses at $3,000, having hit a promotional minimum to secure certain bonuses, he pressed his luck.

His internal governor, not the money, was the issue.

“With all of my skill sets, I have [occasional] problems. What shot does Joe Public have? None.”

Respecting money, and setting and adhering to limits are vital player attributes. Tapping the grocery or rent budgets to bet? Danger. The industry bears equal responsibility.

He taps his phone. A buxom blonde, wearing a skimpy top and short shorts, flips a coin to determine a game winner. It has had 100,000-plus views.

“I went after her,” he says. “[Bleep] it. Flipping . . . a . . . coin!? Irresponsible. I understand sex sells, but it isn’t cute — there’s blood on the line!”

Krack embraces being an industry watchdog.

“I love that role. I understand how it can happen. Everyone starts out a loser and most stay a loser, as far as betting goes. I’m trying to help people, too.”

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