Thomas McPeek didn’t just stumble into a lucky streak — he studied for it.

The 24-year-old from Chicago spent last year diving into the world of sports betting, placing dozens of complex, high-risk wagers on football — called parlays — based on odds he believed he could beat.

“It was a calculated attack where I thought I had an edge,” McPeek told CBS News Chicago.

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In August, he visited the sportsbook at the Horseshoe Casino in Hammond, Indiana, owned by Caesars Entertainment. To ensure his bets wouldn’t be rejected, he remained anonymous, making multiple small bets at kiosks instead of with a clerk at a counter.

He even went so far as to disguise himself with sunglasses or hiding his hair.

Over the course of a single week, McPeek says he bet around $30,000 and won $350,000.

A month later, he traveled across state lines to employ the same strategies at another Caesars property — the Isle Casino in Bettendorf, Iowa. This time, he says his tickets totaled about $450,000 in winnings.

But McPeek says when he tried to cash in, both casinos voided his tickets, citing house rules and anti-money-laundering policies. He says he’s willing to sue to get his winnings.

Where’s the money?

McPeek maintains that he played by the rules but Caesars says he tried to circumvent them, particularly by crossing state lines — something that can violate betting regulations.

Scott Morrow, a former casino executive who now teaches gaming at the University of Nevada—Las Vegas, says Caesars was justified in voiding his tickets on those grounds.

“I have a tough time finding sympathy for his case,” Morrow said.

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But Eli Feustel, a seasoned betting expert and author, sides with McPeek — not because of how the bets were made, but because of Caesars’ timing in voiding his wins. He argues that the casinos only acted after realizing McPeek might actually win.

“The clear answer is Caesars owes this,” he told CBS News.

The Indiana Gaming Commission says Caesars followed the rules. Now, regulators in Iowa are reviewing McPeek’s complaint.

Against the odds

Caesars has banned McPeek from playing at their casinos but is willing to pay back the money McPeek used to place the bets.

Blue Chip Casino in Michigan City, Indiana, also banned McPeek from playing at their casino after he won $127,000, but at least Blue Chip paid him out first.

With Americans spending more than $60.4 billion on commercial casino gaming and sports betting in 2022 — up 14% from 2021 — some wonder if the house plays fair when the odds shift in the bettor’s favor.

For gamblers navigating the high-stakes world of sports betting, McPeek’s case is a cautionary tale.

Here are three ways to ensure you can cash in on your sports bets.

  1. Read the fine print before you place any bets. Sportsbooks include detailed rules in their terms and conditions — including the right to void wagers. Knowing those rules ahead of time can keep you from betting into a gray area.
  2. Keep your bets to one jurisdiction to avoid raising red flags and accusations of gaming the system.
  3. Document everything as you game, from screenshots to transaction receipts. Keeping a trail could make or break your case if things get contested.

Even if the odds are in your favor, the rulebook — and how it’s enforced — might not be.

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This article provides information only and should not be construed as advice. It is provided without warranty of any kind.