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Chicago White Sox defy the odds as worst baseball bet ever

The Chicago White Sox (Andrew Benintendi pictured) drew plenty of interest from sharp and casual bettors alike despite a historically bad season. Photo by Katelyn Mulcahy/Getty Images

Only one baseball team has lost more games in a season than the 2024 Chicago White Sox: the 1899 Cleveland Spiders. The Spiders lost a record 134 games that season, with a minus-732 run differential, and were disbanded the following year.

The White Sox aren't quite in the Spiders' class of futility -- they entered the final week of the regular season at 36-120 with a minus-320 run differential and are expected to field a team again next season -- but to bettors and bookmakers, the ChiSox are in a class of their own and will go down as either the worst team to bet on or the best team to bet against over a season in recent memory.

Mathematically eliminated from the postseason in mid-August and realistically long before then, fans gave up on the White Sox a while ago. Players and coaches are trying to laugh their way through the end of a dismal campaign. Bookmakers are ready for it to be over, too, because attracting a bet on the White Sox has been challenging. There's been plenty of action on their opponents, though.

"It's impossible," veteran bookmaker Craig Mucklow of Caesars Sportsbook laments. "People look to oppose the White Sox every day."

It's been a good strategy.

Fading the White Sox

Betting on baseball traditionally is based on the money line, the odds to win a game straight up. Websites like Covers.com track how much a bettor would be up or down if they bet $100 on a team in every game. If an unlucky bettor put $100 on the White Sox in every game this season, they'd be down approximately $6,100. A 60-unit loss is extraordinary and easily the worst season on the money line in over two decades. According to Covers, the 2018 Baltimore Orioles are the only other team to finish a season down more than $5,000 in the past 20 years.

Consistently betting on the White Sox has not been a popular approach this season, but some bettors have been repeatedly betting against them. Brad Bartel, an avid bettor from Chicago, began betting against the White Sox every game during their record-tying 21-game losing streak in July.

"Once they got on that streak, it seemed like there was no end in sight for them losing," Bartel told ESPN. "So, at that point, I decided it would be a fun and funny thing to do, especially being located here in Chicago."

Bartel's daily fade of the White Sox led to the creation of a group chat with betting buddies titled "White Sox L's." He's been betting against the White Sox in every game for over a month, often risking $200 or $300 on the favored opponents to win $100. He sees no reason to stop fading the White Sox now and plans to continue to do so throughout the remainder of the season.

"In total, I think I'm up about $1,500," Bartel said.

Are the White Sox the sharp side?

On July 22, a customer with BetMGM placed a $1 bet on the White Sox to win the World Series. It was the last World Series bet on the White Sox the sportsbook took before the team's odds were taken off the board in mid-August. The largest World Series bet on the White Sox all season at BetMGM was $150 at 500-1 odds. Those World Series wagers will be staying with the sportsbooks, but bookmakers have taken their lumps trying to deal with White Sox games this season.

"On a day-to-day basis, we're going to be cheering for the White Sox," Halvor Egeland, senior trader for BetMGM, told ESPN. "They certainly haven't been great to us this year."

Attracting any consistent betting action on the White Sox has been difficult for months, bookmakers say, while their opponents draw plenty of interest from bettors, despite having to lay hefty odds. For example, to win $100 on the Baltimore Orioles in their Sept. 2 game against the White Sox, you would have needed to risk upward of $440.

"We try to price them up appropriately," Egeland said, "but it is kind of a challenge. We're not going to put up -700 on a baseball game."

Bookmakers have used the run-line -- baseball's equivalent of the point spread -- to try to drum up more action on the White Sox, giving them plus-2.5 or 3.5 runs in a game. The bulk of the action, though, is on White Sox opponents, who are regularly tacked onto parlays as a perceived free bingo spot.

Occasionally, the plus-money price on the White Sox will reach a point where sharp bettors can't resist.

"When we do see some money coming in on the White Sox, Egeland said, "it's usually going to be the sharper money."

Mucklow, Caesars' bookmaker and a seasoned bettor himself, said he bet on the White Sox nine times this year, because the odds were simply too attractive. "I lost all nine games," he said.

White Sox bettors 'deserved a better fate'

Expectations certainly weren't high entering the season, but no one -- not oddsmakers nor bettors -- expected the White Sox to be this bad. The team had better opening odds to win the World Series (150-1) than the Oakland A's (500-1), Colorado Rockies (250-1) and Kansas City Royals (200-1) at some sportsbooks, and the over/under on the White Sox season-win total was set around 62, higher than at least two teams.

"I was considering betting them over until they unloaded their ace Dylan Cease before the season opened," Michael "Roxy" Roxborough, an iconic Las Vegas oddsmaker and longtime respected baseball bettor, said.

Roxborough wasn't alone. The bulk of the money bet on the White Sox season-win total was on the over, and while that action may look square now, the odds of them winning only around 40 games were long. They shouldn't be this bad, oddsmakers say.

The statistical metrics Roxborough uses to handicap baseball, even sophisticated ones such as Pythagenpat and Base runs, indicate the White Sox should've won at least 8 to 11 more games than they have.

"Even a simple metric like run differential indicates that the White Sox should have won many more games," Roxborough said. "You cannot go to the cashier's window with stats, but if you were betting on them each game, you deserved a better fate."