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.
Oleksandr Usyk has shared his reaction to Anthony Joshua‘s dramatic knockout victory against Kristian Prenga.
Usyk nearly suffered his own shock defeat in May when he was pushed to the limit by kickboxing star Rico Verhoevenand two months on it was nrw teammate Joshua’s turn to come close to a massive upset loss that would have stunned the heavyweight division.
The Brit was dropped twice by massive underdog Prenga in the opening round of their clash in Jeddah, Saudi Arabia on Saturday, but ‘AJ’ managed to recover and record a big knockdown of his own in the second round that resulted in the stoppage victory.
Joshua and Usyk now train together, having famously had two battles for the unified world heavyweight title in 2021 and 2022, and the Ukrainian has had his say on his stablemate’s victory over Prenga.
Speaking to TalkSporttwo-time undisputed champion Usyk praised Joshua, insisting ‘AJ is back’ before predicting that Joshua will now claim a knockout win over long-term rival Tyson Fury in his next bout.
“Anthony Joshua is next undisputed champion. First round it’s a test but AJ is back.
It’s boxing, [the] big upper cut is good, it’s a knockdown. AJ [come] back and win.
“Greedy Belly [Fury] will speak now and say weak chin, Greedy Belly get out. AJ wins [against Fury], [he will] knock him out.”
Fury was victorious on Friday as he earned a seventh round retirement win against Mariusz Wach in Thailand, paving the way for the showdown against Joshua later this year.
Jake Paul was the last man to fight Anthony Joshua and he has now revealed his verdict on AJ’s chaotic victory over Kristian Prenga.
Joshua went up against Prenga in Jeddah, Saudi Arabia on Saturdayin a clash that was expected to be a comfortable win for the former world heavyweight champion in order to set up the long overdue battle against Tyson Fury.
Any hopes of seeing that clash were nearly ended after AJ was dropped twice in the opening round of the bout, though he was able to recover and claim the second round knockout to come out on top and prevent a stunning shock upset from taking place.
Saturday’s outing saw Joshua back in the ring for the first time since his sixth round triumph over YouTuber-turned-boxer Jake Paul back in Decemberand now ‘The Problem Child’ himself has shared his reaction to his former rival’s victory over Prenga.
Posting on social mediaPaul praised AJ for earning the win, after returning to action following the tragic car crash he was involved in at the end of last year which took the lives of his two close friends.
“Happy for Joshua with that win after all he’s been through. Remembering Sina and Latz with this one.”
Happy for Joshua with that win after all he’s been through.
Remembering Sina and Latz with this one.
— Jake Paul (@jakepaul) July 25, 2026
The win for Joshua should now tee up for meeting with Fury later this year, after ‘The Gypsy King’ held up his end of the bargain by also securing a win in his warm-up bout on Friday, securing a seventh round retirement win against Mariusz Wach.
Anthony Joshua may have earned a knockout win over Kristian Prenga but the fight certainly didn’t unfold as most people expected.
Joshua was facing the Albanian in Jeddah, Saudi Arabia on Saturday, and it looked like a massive upset could be on the cards when he was dropped twice in the opening round.
‘AJ’ was able to recover and went on to secure a second round knockout victory to prevent the shock lossseemingly paving the way for the battle against Tyson Fury later this year.
One man who was ringside to witness the battle was former cruiserweight world champion Tony Bellewand he praised Joshua’s ability to turn things around in the fight after describing it as ‘chaos’.
“We predicted round two but I don’t think we foresaw that. That was chaos. He doesn’t see the uppercut coming and finds himself on the floor without knowing how he got there.
“The second one he did see it coming and he was able to clench down on the jaw. He got up and then the experience that he has he used tonight because he tied him up. Against Andy Ruiz he didn’t know what he was doing and didn’t know how to do that, but tonight he did.
“He showed once again there is no quit. To be that hurt in the first round and get up, that’s the recoveries of power. People talk about your chin, but it’s not, it’s the level of fitness that gets you up from the floor.
“When Joshua gets a fighter hurt he’s the best finisher in the division. Whenever he hurts someone they’re gone. I haven’t seen him drop anybody and they survive, only Andy Ruiz. He’s a ruthless finisher.”
The clash between Joshua and Fury is now expected to be announced soon for later this year, after Fury won his own interim fight on Friday by defeating Mariusz Wach.
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