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The wildest sports bets of 2025, from the Pope to Jake Paul to the CFP

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It’s basic to say now that we have a year behind us, but looking back at 2025, some betting decisions may have been… miscalculated.

Some examples:

  • Last season, DraftKings said it placed a $25,000 bet on the Las Vegas Raiders to win the Super Bowl at 100-1. The Raiders would not win the Super Bowl.

  • 102 entries to Circa Survivor, a high-stakes NFL survivor competition run by a Las Vegas casino, did not submit their picks by the weekly deadline this season and were eliminated. The tournament buy-in was $1,000 and the prize pool was $18.7 million.

  • Kalshi Prediction Market noted that one of its clients invested $183,954 in social media influencer-turned-boxer Jake Paul to defeat vigorous two-time heavyweight champion Anthony Joshua. Paul was hospitalized with a broken jaw thanks to Joshua’s devastating right hand during the knockout victory. Live and learn, right?

This year hasn’t been a bad one for gamblers at all. There have been several betting success stories that have had bookmaking executives lamenting to shareholders about “customer-friendly results” or begging gambling regulators to allow them to void angle shooting contracts altogether. Despite these setbacks, the betting industry is expected to survive the up-to-date year.

As we reflect on the year in betting, we wish you fewer miscalculations in 2026.

The craziest bets of 2025

January 9: A DraftKings bettor placed a 50-cent 19-game college basketball bet at odds of +43,473,946. All 19 teams covered the spread; 17 of them came from compact conferences, including Stetson, Jacksonville and IU Indianapolis.

The 50-cent jackpot won $217,370.23.

January 28: A DraftKings bettor placed a $1,000 bet on Indiana Hoosiers quarterback Fernando Mendoza to win the Heisman Trophy at odds of 100-1. Eleven months later, in December, Mendoza received the Heisman Award, which resulted in a net winning of $100,000.

February 9: The Philadelphia Eagles defeated 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, according to the bookmaker.

April 21: Sportsbooks began noticing an unusual spike in home run bets on Wednesday morning at the start of the MLB season. The bets were not on Aaron Judge or Shohei Ohtani. They involved Nick Castellanos, a journeyman outfielder for the Philadelphia Phillies and the subject of an Internet meme that has earned him a reputation for returning home on gigantic news days.

“We started looking around to see what was going on and we saw that the Pope had died,” recalled BetMGM’s Halvor Egeland.

Egeland said BetMGM rarely charges enough on a home run bet to adjust the odds, but it did that day, dropping Castellanos from +775 to +550. This didn’t leisurely down the action. By the end of the day, more bets had been placed on Castellanos’ homer than on any other team or player in all sports.

Castellanos went 0-for-4 with two strikeouts in the Phillies’ 5-4 loss to the Novel York Mets.

June 5: A bettor from Ohio with BetMGM placed a bet An $8 million bet on the heavily favored Oklahoma City Thunder, who defeated the Indiana Pacers in the NBA Finals at -700 odds.

The Thunder defeated the Pacers in seven games, with bettors net winning $1.42 million.

June 15: JJ Spaun shot 150-1 to win the US Open. Spaun had the best chance to win of any player since Phil Mickelson (200-1) won the 2021 PGA Championship.

June 24: An Arizona bettor using BetMGM placed three gigantic bets on the winner of the College Football Playoff:

$300,000 to Texas at 5-1
$200,000 at Penn State at +750
$115,000 for Clemson at 13-1

All three teams missed the CFP.

June 25: The Dallas Mavericks selected Cooper Flagg with the No. 1 overall pick in the NBA Draft. The Mavericks were 500-1 to select Flagg, the highest odds of any futures bet offered by DraftKings in 2026.

August 23: Heading into the college football season, North Carolina, under first-year coach Bill Belichick, attracted the same amount of money and wagering to win the national championship as Indiana on BetMGM Sportsbook. The Hoosiers finished the season undefeated and entered the CFP with the top seed, while the Tar Heels finished 4-8.

August 30: A DraftKings bettor picked the winner of all 15 MLB games this Saturday, who won $125,088.36 in a $5 15-game bet deal.

August 31: A FanDuel player followed beloved college football personality Lee Corso College Gameday final picks and won $1,317.18 in a six-game $10 giveaway that included outright wins over Florida State and Alabama. Corso retired from the series this year.

September 7: The Buffalo Bills staged a remarkable comeback by beating the Baltimore Ravens 41-40 on Sunday in the first week of the NFL season. According to the bookmaker, this transaction resulted in the largest winnings in any game for BetMGM customers this year. In an earnings call, DraftKings said the Bills-Ravens partnership had the biggest loss in the sportsbook’s history.

September 11: A bettor at Caesars Sportsbook risked $715,000 on +140 underdog Terence Crawford to defeat Canelo Alvarez and netted $985,000 as Crawford won by unanimous decision.

October 15: A Massachusetts bettor operating DraftKings placed 27 parlay bets centered on how many hits Toronto Blue Jays outfielder Nathan Lukes would have in the American League Championship Series game against the Seattle Mariners. The player risked $12,950 for a chance to win $934,147.83.

DraftKings has informed the Massachusetts Gaming Commission (MGC) that a technical error allowed a bettor to include Luke’s five-plus, six-plus, seven-plus and eight-plus hits during the ALCS in sports betting to boost the odds. Lukes had nine hits in the ALCS.

DraftKings told MGC it believes the player’s relative is among six customers in Novel Jersey who also placed a similar bet on Lukes, resulting in a $1.8 million winnings. Gaming regulators in Massachusetts and Novel Jersey rejected DraftKings’ request to void the bets.

November 2: A week after National Tight End Day, a bettor at Caesars Sportsbook bet on five tight ends and scored the first touchdown of his parlay series. Four of the five players – Theo Johnson of the Novel York Giants, Tyler Higbee of the Los Angeles Rams, Dalton Kincaid of the Bills and Sam LaPorta of the Detroit Lions – returned the win to the bettor, resulting in winnings of approximately $111,000.

“The customer bet on each combination of these five selections and bet $2.50 per leg, and the potential winnings were just under $2 million,” said Joey Feazel of Caesars Sportsbook. “Although the bettor missed all five, he hit four of five, allowing him to win over $111,000. A fantastic investment for the bettor.”

December 7: A Demanding Rock BET bettor placed a $1.20 bet involving all college basketball players, resulting in a payout of $344,902.81. According to the company, at +34,490,181, this is the highest ever odds for a successful deal at Demanding Rock BET.

December 8: A Fanatics bettor placed $1.47 million on a four-game NFL bet in Week 14, netting him $1.86 million, the sportsbook’s biggest winning bet of the year. Four legs: Rams money line over Arizona Cardinals; Green Bay Packers Moneyline over Chicago Bears; and Denver Broncos over Raiders and under at Pittsburgh Steelers-Ravens (alternate line).

December 14: The player successfully predicted that a player would score the first touchdown in five NFL games, turning a 10-cent winnings into a payout of $7,356.80.

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Boxing

Bill Haney commented on the Keyshawn Davis situation, says Shakur Stevenson’s fight is the most significant

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Image: Bill Haney Addresses Keyshawn Davis Situation, Says Shakur Stevenson Fight Comes First

“This man said he wanted the number 144,” Bill told Fight Hub TV. “He said, ‘We’ve got to sit down like businessmen and make this happen,’ right? Well, we’ve already sat down like businessmen. We’re ready to make it happen.”

Elder Haney also rejected suggestions that the catchweight proposal would represent a sudden change of plans.

“It’s not so sudden. 144 is a welterweight. Are you crazy or what?” Haney said. “At welterweight, we range from 140 to 147.”

As the conversation turned to Keyshawn Davis and his position as a top contender for the WBO title, Haney repeatedly pointed to what he believed to be a better opportunity.

“What is the most significant boxing fight going on right now?” Haney asked. “Shakur Stevenson and Devin Haney.”

Haney acknowledged that Davis remains part of the bigger picture, but pointed out that Stevenson’s matchup has been years in the making.

“This case has been brewing for seven, eight, nine, 10 years, whatever it was,” Haney said. “Just rest and we’ll get it done. He’s on the list. He was on the list before he was on the list, and he’ll stay on the list.”

Time will tell if the fight comes to fruition, but Bill Haney’s comments were perhaps the strongest indication yet that Team Haney is sedate about racing Stevenson at the proposed catchweight of 144 pounds.

The situation could become more complicated if the WBO formally orders Haney to fulfill his mandatory obligation to Davis. Until then, it appears the Haneys are turning their attention to what they believe is the biggest fight available.

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Oscar De La Hoya says Gervonta Davis doesn’t deserve to have an undefeated record before her comeback

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Oscar De La Hoya says that Gervonta Davis does not deserve undefeated record ahead of comeback

Oscar De La Hoya believes Gervonta Davis’ professional record should see a loss ahead of his potential comeback fight.

It is said that the 31-year-old is in negotiations for a fight for the WBA lightweight title with Floyd Schofield Jr, offering “Tank” the opportunity to regain his elderly belt.

Davis defended his world title after: controversial draw with Lamont Roach in March 2025, but has since become the sanctioning body’s “halt champion” at 135 pounds.

This is partly due to his passivity, but also to the American’s problems outside the ring, where he faced accusations of domestic violence.

However, it currently appears that Davis could return to action soon, with a potential fight with Schofield set for September or October.

These negotiations involve Schofield’s promoter, Golden Boy boss De La Hoya, who insists that “Tank” should suffer his first professional defeat in the match against Roach.

Their match ended in a draw after referee Steve Willis ruled against a knockdown in round nine when Davis clearly touched the canvas following a shot by Roach.

As a result, De La Hoya said Fighting Hub TV that Roach should have back-to-back victories over “Tank” and Isaac “Pitbull” Cruz, whom he boxed in December to a less controversial draw.

“Roach is a great fighter in his own right. He has some really good wins under his belt. I say he wins because I think he really won against ‘Tank’ Davis and I think he did a great job against ‘Pitbull.’

If Davis and Schofield’s respective teams are unable to reach an agreement by June 22, their mandate quarterback will be sent to a bidding hearing.

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Shakur Stevenson accuses Devin Haney of ‘false public negotiations’ after £144 settlement

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Image: Shakur Stevenson Accuses Devin Haney of "Fake Public Negotiations" After 144-Pound Agreement

Potential negotiations between Devin Haney and Shakur Stevenson have taken another public turn after Stevenson accused his rival of engaging in “false public negotiations” following Haney’s latest comments on social media.

Haney appeared frustrated after previously agreeing to Stevenson’s proposed catchweight of 144 pounds, suggesting that even accepting those terms did not bring the fight any closer to becoming a reality.


“144 is not enough…I still don’t want to fight! Damn…@ShakurStevenson,” Haney wrote X.

Shakur later responded by dismissing this public exchange as a impoverished reflection of how main event fights actually unfold.

“The same thing you all did with Rolly. All those counterfeit public negotiations… The real negotiations take place offline.” I am the truth that you will see when you stand before me!!” Shakur posted.

Shakiur previously considered 144 pounds to be a fair compromise in a potential showdown with Haney, who has competed at welterweight in his most recent outings. Haney then signaled his willingness to accept the catchweight offer, sparking optimism that one of boxing’s most talked-about fights could gain momentum.

The latest exchange came shortly after the WBO confirmed that Haney must either defend his welterweight title against mandatory challenger Keyshawn Davis or risk losing the belt. While neither Haney nor Stevenson directly addressed the situation in their recent posts, the article did add another note to any future negotiations involving the former two-division world champions.

With Haney facing a WBO title decision and Shakur insisting that stern negotiations will take place behind closed doors, the pressure is now on both camps to determine whether the fight can go beyond an online exchange.

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Categories Devin Haney, Keyshawn Davis and Shakur Stevenson

Last update: 2026/06/12 at 21:45

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