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    Parlays are one of the most popular and exciting forms of sports betting around. It combines various bets into one, giving the bettor a chance at a lucrative payday. They are, however, very difficult to hit – but not impossible. 

    There are various stories of bettors turning anything less than $5 into six-figure digits. It’s nearly impossible, but still possible to hit a big parlay. Let’s go through the biggest and craziest parlays to ever hit and some interesting information behind them.

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    Has Anyone Hit a 25 Leg Parlay?

    Common parlays can range anywhere from two to 10 legs, but what about a 25-leg parlay? Kevin LaRose from New Jersey nailed a 25-leg college basketball parlay in which he turned $25 into $237K. LaRose is only the most recent 25-leg parlay winner, as the book he bet with (Caesars) has seen 112 different 25-leg parlay winners in its history. 

    He did, however, smash the payout record for a 25-leg parlay by winning $237K. The previous highest payout from a 25-leg parlay was only $3.4K. On LaRose’s parlay ticket, his longest moneyline odds were Wake Forest ML over USC Upstate at -4500 and his shortest was UIC over Central Michigan at -250.

    LaRose had 15 moneyline wagers and 10 spread wagers in his parlay. All his spreads were -110 moneylines, with only two underdogs to cover. Those underdogs were Minnesota at +13.5 vs. Michigan and UTSA at +6.5 against Sam Houston State. The largest favorite taken was Kansas at -23 over Missouri.

    Craziest Parlay Wins

    Besides LaRose’s 25-leg parlay, there are plenty of other crazy parlays to hit over the sports betting years. 

    New York Bettor Turns $6.90 into $219K

    In 2022 a New York bettor at Caesars hit a 16-leg parlay that turned just over $5 into nearly $220K. The bettor went through multiple sports to hit it, going with 10 MLB games and two pairs of NBA and NHL Playoff games. 

    Three of the 10 MLB games actually went into extra innings, if the parlay was nerving as is. Of the 10 MLB bets made, nine were moneyline bets. Milwaukee at -1.5 was the only run line wager, as five of the nine moneyline bets were actually for the underdogs. 

    Both NHL Playoff bets were moneyline wagers for favored teams, while the pair of NBA Playoff games were ATS wagers for favorites as well. The Oilers at -210 were the largest moneyline odds for a favored team on his ticket, as Edmonton beat the Kings 6-0. 

    Marco Piemonte Turns $30K Into $1.2 Million

    In 2022, Marco Piemonte threw $30K on a five-leg parlay with the chance to win $1.2 million dollars. Four of the five legs hit as Piemonte just needed the Georgia Bulldogs to beat the Alabama Crimson Tide, something that hadn’t occurred in 15 years until that point. 

    Piemonte hit an NFL spread and three NFL moneylines prior, two of which were underdog plays. The payout odds with PointsBet showed a +3923, as Piemonte was also able to cash out at $624K prior to the Georgia-Alabama game. It’s a good thing he decided to keep playing.

    50 Cents Turns Into $130K

    This parlay was the combined effort of three bettors from Pennsylvania. The three bettors threw together an incredibly rare market parlay, the first basket scorer market. In it, a bettor wagers on which player will score the first basket in a game. Getting one right is very difficult, but getting six right in a parlay is incredibly rare. 

    50 cents saw $130K with the six different first basket scorer plays. LeBron James of the Los Angeles Lakers saw the shortest odds of the six at +370. Lauri Markkanen of the Cleveland Cavaliers (at the time) had the longest odds on the ticket at +1100.

    Las Vegas Bettor Turns $5 Into $305K

    In 2016, a Las Vegas bettor won $305K off a $5 parlay with a William Hill sportsbook. The bettor hit a ridiculous 15-leg parlay by picking straight up basketball winners on a progressive parlay card that had been offered by William Hill. 

    Of the 15 games, the bettor selected 12 college hoop contests and two NBA games. The final game came down to Kansas vs. Texas, in which the Jayhawks won by 30 points. The bettor hedged the game, however. 

    NHL Bettor Turns $5 Into $89K

    In 2022, a FanDuel bettor turned $5 into a near $100K by betting on… wait for it… hockey goal scorers. Yes, an extremely niche market made even more difficult in the form of a parlay hit in January of last year. The bettor hit 10 different goal scorers across 10 different NHL games. 

    $1.10 Parlay Wins $532K

    A 23-leg parlay netted half a million dollars for a bet that cost $1. Not every bet landed on the 23-leg parlay though, as some bets were a push. This means the payout would’ve actually been more should a few legs actually won and not be pushed. The parlay was a nice mix of spreads and moneylines but all on college basketball games. 


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