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.
Deontay Wilder appears to be in talks for his next appearance, which may include negotiations with Matchroom Boxing promoter Eddie Hearn.
The former WBC heavyweight champion scored a split decision victory over Derek Chisora in April, scoring two knockouts in a mostly close 12-round fight.
Chisora’s triumph therefore came at a critical moment, although many remain convinced that the 40-year-old should implement his retirement plan.
An imminent departure from the sport, however, seems increasingly unlikely as the ‘Bronze Bomber’ is currently considering a possible rematch with fellow veteran Chisora.
Unlike Wilder, Chisora promised that their first meeting would be his last fight, believing that his 50th professional fight would be a suitable event from which he would retire.
However, the way their clash ended inspired the 42-year-old to demand an immediate rematch, hoping for a more favorable outcome next time.
I’m talking to Daily mail boxChisora managed to get a response from Wilder via FaceTime, and the American expressed interest in withdrawing him.
“Hell yes. We’ll make it happen.”
Chisora added that he intended to speak to Hearn, suggesting he was a free agent with the promotion and wanted to strike a deal with the Matchroom boss.
However, although he verbally agreed to a rematch, there is of course no guarantee that Wilder will ultimately put pen to paper.
Elijah Holyfield, son of former undisputed heavyweight champion Evander Holyfield, won his first WWE Evolve match on June 3, defeating Kai Kavari in the company’s developmental program.
According to material published by Bleacher ReportHolyfield ended the fight with a right hand and pinned Kavari. WWE calls the finisher “The Uppercut”, a move modeled after his father’s boxing. Pro Wrestling Dot Net reported that the fight lasted 1 minute and 14 seconds.
According to SEScoops, Holyfield went through a series of Stinger Splashes and Spinebusters before delivering the final blow.
His father, a former cruiserweight and heavyweight world champion and member of the International Boxing Hall of Fame, built much of his ring identity on body striking and combination work during a career spanning the 1980s, 1990s and 2000s.
From the NFL to the ring
Holyfield’s path to WWE didn’t go through boxing. He played running back at the University of Georgia and signed with the Carolina Panthers as an undrafted free agent in 2019 and later spent time with the Philadelphia Eagles and Cincinnati Bengals. He appeared in one regular-season NFL game during the 2020 season.
A 2022 knee injury he suffered while on the Bengals’ roster ended his football career and redirected him toward wrestling.
WWE path
Holyfield signed a WWE developmental contract in November 2024. He competed in the first season of the WWE reality show LFG (Legends and Future Greats), where he mentored The Undertaker and earned a contract that placed him on the Evolve brand.
His ring debut was delayed due to injury. According to multiple wrestling outlets, he suffered a torn bicep in delayed 2025 and required surgery. He is 27 years ancient.
The June 3 episode of Evolve was taped at the WWE Performance Center in Orlando, Florida and streamed on Tubi in the United States.
On Thursday, Matchroom Boxing announced that Taylor will return to Dublin’s Croke Park on September 5 to defend her WBO, WBA, IBF and Ring Magazine titles against undefeated French challenger Flora Pili. The vacant WBC title is also at stake, giving Taylor a chance to become a three-time undisputed champion.
The event will be broadcast live worldwide on DAZN and is expected to attract over 80,000 fans to Ireland’s national stadium.
“It seems like the perfect way to end – to become Undisputed Champion once again on our national stadium that holds such a special place in Irish hearts. I’m grateful that this is happening and I can’t thank the people of this country enough for the support I’ve received over the years.
“People have traveled all over the world following my career and I hope I can return the favor with a confident performance on September 5. I have no illusions that Flora will pose a very arduous challenge; she is undefeated as a professional and has a good amateur pedigree, so I have the utmost respect for her.
“I have been blessed to have achieved more in this sport than I could have ever dreamed of, but fighting in Croke Park is truly the icing on the cake. I hope this event inspires a whole recent generation to take up sport and follow their passions.”
Taylor enters the fight with a 25-1 record. The event, which will take place on September 5, will be the first professional boxing event held in Croke Park since Muhammad Ali fought Alvin Lewis there in 1972.
Pili brings an undefeated record of 12-0 to the fight and will be looking for the biggest victory of his career. Tickets go on sale June 12 via Ticketmaster, with pre-sales starting earlier this week.
If successful, Taylor will retire as a three-time undisputed champion.
Olly Campbell is a boxing journalist covering this sport since 2014, providing reports from the ring and technical analyzes of the most critical fights. His work focuses on fighter tendencies, tactical adjustments and the details that shape high-level competition.
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