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.
Top trainer and former world champion Robert Garcia has considered the outcome of a fantasy showdown between Terence Crawford and Manny Pacquiao.
The two generational greats reportedly came close to squaring off in 2021, back when Crawford was the WBO welterweight champion and ‘Pac Man’ held the WBA title.
Their unification match never materialised, though, as Pacquiao was scheduled to face Errol Spence Jr before ‘The Truth’ pulled out with a torn retina.
Instead, the Filipino legend ended up losing his WBA title to Yordenis Ugas at a stage when, while still serviceable, he was quite clearly past his best.
Crawford, meanwhile, was hitting top form around this time, just a few fights away from producing arguably a career-best performance against Spence.
He did, of course, manage to stop his welterweight rival in nine rounds, before moving up to 168lbs and becoming a three-division undisputed champion by dethroning Canelo Alvarez last September.
Based on those two performances, coach Garcia has told ESNEWS that he would favour ‘Bud’ to defeat even a prime version of Pacquiao.
“The Crawford that beat Spence – and the Crawford that beat Canelo – would probably beat Manny.”
While Crawford’s prime almost certainly came during his run of eight stoppages at welterweight, it is harder to pinpoint when Pacquiao ultimately reached his peak.
In terms of his most destructive performance at world level, however, many will point towards his second-round finish over Ricky Hatton in 2009.
While facing the ‘Hitman’ at 140lbs, Pacquiao would cement himself as a formidable welterweight champion soon after, dethroning Miguel Cotto with a 12th-round stoppage for the WBO title.
Former world champion Oleksandr Gvozdyk has been left between a rock and a hard place afterhis promotional contract with Zuffa Boxing has been terminated.
The Ukrainian dethroned long-reigning light-heavyweight champion Adonis Stevenson in 2018, scoring an 11th-round stoppage that left his opponent with a brain injury.
Gvozdyk then made a WBC title defence before losing to Artur Beterbievwho extended his ruthless surge with a 10th-round finish in their 2019 encounter.
Since that defeat, ‘The Nail’ suffered a unanimous decision loss to David Benavidez in 2024, before entering a perceived 50/50 contest against Radivoje ‘Hot Rod’ Kalajdzic in February.
With both making their Zuffa debut, the two veterans delivered a thrilling battle in which Gvozdyk scored two knockdowns and had built a sizable lead.
In round seven, though, the 39-year-old found himself on the canvas and was ultimately stopped on his feet after getting dropped a second time.
Given his overall performance, one would suspect he had done enough to justify another meaningful opportunity, yet Gvozdyk has since told vRINGe that he will no longer be fighting under the Zuffa banner.
“They terminated the contract in February after a loss. That is, every promoter has the option that if a boxer loses, they have the right to terminate the contract. That’s exactly what they did. After the fight, everyone was saying how great it was. That everything was great. I rested. I started preparing as planned – somewhere around May. And then, around April, they told me I’d received an email terminating the contract.”
This is because his contract has been terminated, while Kalajdzic’s next outing with Dana White’s promotional outfit is confirmed for September 26 against Craig Richards.
As for Gvozdyk, it is difficult to predict what will come next but, at the age of 39, one would suspect that he is close to hanging up the gloves.
Still, he could hardly have been happy to part ways with Zuffa, which also terminated its contract with Robert Meriwether following his defeat to Tony Hirsch Jr in April.
Former British champion and Olympic bronze medallist David Price has assessed whether his countryman, Conor Bennpossesses the necessary hand speed to defeat Ryan Garcia.
The two welterweights will square off at Las Vegas’ T-Mobile Arena on September 12, with Garcia making a first defence of his WBC world title.
It was arguably a career-best performance that saw him dethrone Mario Barrios in February, scoring a first-round knockdown before winning a wide unanimous decision.
But despite coming off this dominant display, Garcia was far less impressive when he returned from a year-long doping ban and lost on points to Rolando Romero in May 2025.
Still, many would argue that the 28-year-old has shown signs of world-class quality, while Benn remains glaringly unproven at the top level.
The 29-year-old has also not fought at 147lbs since 2022, with his last two outings resulting in unanimous decision victories over faded versions of Chris Eubank Jr and Regis Prograis.
Against Eubank, in particular, Benn’s speed seemed a key factor in their two middleweight encounters last year, despite him suffering a points defeat the first time around.
As he approaches this welterweight contest against Garcia, though, former heavyweight contender Price has told The Smith Brothers that he sees Benn contending with an unfamiliar disadvantage.
“I think I [favour Garcia]. Conor Benn’s got great hand speed, but I think [Garcia’s] hand speed could make the difference in the fight.”
Like Garcia, Benn tested positive for a banned substance – clomifene – and was eventually removed from his cancelled 2022 encounter with Eubank.
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