It’s easy to say this now with the year behind us, but looking back at 2025, some betting decisions were, perhaps … miscalculated.
A few examples:
This past offseason, DraftKings reported taking a $25,000 bet on the Las Vegas Raiders at 100-1 to win the Super Bowl. The Raiders would fall very short of winning the Super Bowl.
102 entries in Circa Survivor, a high-stakes NFL survivor contest operated by a Las Vegas casino, failed to submit their picks by the weekly deadline this season and were eliminated. The contest had a $1,000 buy-in and an $18.7 million prize pool.
Prediction market Kalshi noted that one of its customers invested $183,954 in social-media-influencer-turned-boxer Jake Paul to beat active, two-time heavyweight champion Anthony Joshua. Paul ended up in the hospital with a broken jaw, courtesy of a devastating right hand from Joshua in his knockout victory. Live and learn, right?
The year wasn’t all bad for gamblers. There were some betting success stories that left sportsbook executives lamenting to shareholders about “customer-friendly results” or pleading to gambling regulators to allow them to void angle-shooting parlays altogether. Despite these setbacks, the bookmaking business is expected to survive in the new year.
As we reflect on the year in betting, we wish you fewer miscalculations in 2026.
2025’s wildest bets
Jan. 9: A bettor with DraftKings placed a 50-cent, 19-leg college basketball parlay at +43,473,946 odds. All 19 teams covered the spread; 17 of them were from small conferences, including Stetson, Jacksonville and IU Indianapolis.
The 50-cent parlay won $217,370.23.
Jan. 28: A bettor with DraftKings placed a $1,000 bet on Indiana Hoosiers quarterback Fernando Mendoza to win the Heisman Trophy at 100-1 odds. Eleven months later in December, Mendoza was awarded the Heisman, resulting in a net $100,000 win.
Feb. 9: The Philadelphia Eagles blew out the Kansas City Chiefs in Super Bowl LIX 40-22. BetMGM customers lost more money on the Super Bowl than on any other game in any sport in 2025, the sportsbook reported.
April 21: Sportsbooks began noticing an unusual spike in home run bets on a Wednesday morning, early in the MLB season. The bets weren’t on Aaron Judge or Shohei Ohtani. They were on Nick Castellanos, a journeyman outfielder for the Philadelphia Phillies and the subject of an internet meme that left him with a reputation for homering on days with big news.
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“We started looking around to see what was going on, and saw that the Pope had died,” BetMGM’s Halvor Egeland recalled.
Egeland said BetMGM rarely accrues enough liability on a home run prop to adjust the odds, but they did so that day, shortening Castellanos’ price from +775 to +550. It didn’t slow the action. By the end of the day, more bets had been placed on Castellanos to homer than there were on any other team or any player in all sports.
Castellanos went 0-for-4 with two strikeouts in a 5-4 Phillies’ loss to the New York Mets.
June 5: A bettor in Ohio with BetMGM placed an $8 million bet on the heavily favored Oklahoma City Thunder to beat the Indiana Pacers in the NBA Finals at -700 odds.
The Thunder outlasted the Pacers in seven games, and the bettor won a net $1.42 million.
June 15: J.J. Spaun, a 150-1 long shot, won the U.S. Open. Spaun had the longest odds of any player to win since Phil Mickelson (200-1) won the PGA Championship in 2021.
June 24: A bettor in Arizona with BetMGM placed three large bets on the winner of the College Football Playoff:
$300,000 on Texas at 5-1$200,000 on Penn State at +750$115,000 on Clemson at 13-1
All three teams missed the CFP.
June 25: The Dallas Mavericks selected Cooper Flagg with the No. 1 pick in the NBA draft. The Mavericks were 500-1 to pick Flagg, the longest odds of any single futures wager offered by DraftKings in 2026.
Aug. 23: Entering the college football season, North Carolina, with first-year coach Bill Belichick, had attracted the same amount of money and bets to win the national championship as Indiana at BetMGM sportsbooks. The Hoosiers finished the season undefeated and entered the CFP as the top seed, while the Tar Heels went 4-8.
Aug. 30: A bettor with DraftKings picked the winner of all 15 MLB games that Saturday to win $125,088.36 off a $5, 15-leg parlay.
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Aug. 31: A bettor with FanDuel tailed beloved college football personality Lee Corso’s final picks on College Gameday and won $1,317.18 off a $10 six-leg parlay that included Florida State over Alabama straight-up. Corso retired from the show this year.
Sept. 7: The Buffalo Bills mounted a remarkable comeback to beat the Baltimore Ravens 41-40 in the Sunday prime-time game in Week 1 of the NFL season. The high-scoring affair resulted in the biggest win on any game for customers at BetMGM on the year, the sportsbook reported. In an earnings call, DraftKings said Bills-Ravens produced the biggest loss ever for the sportsbook.
Sept. 11: A bettor with Caesars Sportsbook risked $715,000 on +140 underdog Terence Crawford to beat Canelo Alvarez and won a net $985,000 when Crawford won by unanimous decision.
Oct. 15: A bettor in Massachusetts with DraftKings placed 27 parlay bets centered on the number of hits Toronto Blue Jays outfielder Nathan Lukes would have in the American League Championship Series against the Seattle Mariners. The bettor risked $12,950 for a chance to win $934,147.83.
DraftKings told the Massachusetts Gaming Commission (MGC) that a technical error allowed the bettor to include Lukes five-plus, six-plus, seven-plus and eight-plus hits during the ALCS in parlays to escalate the odds. Lukes recorded nine hits in the ALCS.
DraftKings told the MGC that it believed a relative of the bettor was among six customers in New Jersey who also placed similar parlays on Lukes, resulting in a $1.8 million win. Gaming regulators in Massachusetts and New Jersey denied DraftKings’ request to void the wagers.
Nov. 2: One week after National Tight Ends Day, a bettor with Caesars Sportsbook put five tight ends to score the first touchdown in their respective games in a series of parlays. Four of the five — the New York Giants’ Theo Johnson, the Los Angeles Rams’ Tyler Higbee, the Bills’ Dalton Kincaid and the Detroit Lions’ Sam LaPorta — delivered for the bettor, resulting in an approximately $111,000 win.
“The customer bet every permutation of these five selections and bet $2.50 a leg with a potential win of just under $2 million,” Joey Feazel of Caesars Sportsbook said. “While the bettor did not hit all five, hitting four of the five netted over $111,000 in winnings. A fantastic investment for the bettor.”
Dec. 7: A bettor with Hard Rock BET hit a $1, 20-leg parlay featuring all college basketball unders that resulted in a $344,902.81 payout. At +34,490,181, it’s the longest odds on a successful parlay ever at Hard Rock BET, the company said.
Dec. 8: A bettor with Fanatics wagered $1.47 million on a four-leg NFL parlay in Week 14 that paid a net $1.86 million, the largest winning wager of the year at the sportsbook. The four legs: Rams money line over the Arizona Cardinals; Green Bay Packers money line over the Chicago Bears; and Denver Broncos over the Raiders and under in Pittsburgh Steelers-Ravens (alternate line).
Dec. 14: A bettor successfully predicted the player to score the first touchdown in five NFL games, turning a 10-cent parlay into a $7,356.80 payday.
ESPN’s Doug Greenberg contributed to this story.
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