Red Sox’s historic win streak has caused massive betting market disruption

How can you not be romantic about baseball?

The Red Sox have turned a once forlorn season on its head with a 14-game win streak that has launched them inside the American League wild-card picture.

Boston, which entered July with 125/1 World Series odds, has slashed its outlook to 25/1 at DraftKings Sportsbook entering Tuesday’s game against the Orioles at Fenway Park. 

This is a club that spent the season’s first three months in last place in the AL East and, as recently as June 24, owned the American League’s worst record at 32-46, sat 15 ½ games out of first and were all but destined to sell house at the trade deadline.

The Red Sox were scrutinized for a lack of direction after another cost-conscious offseason that saw Alex Bregman walk to the Cubs. Things only grew more uncertain when they fired player-favorite manager Alex Cora on April 25 following a 10-17 start and promoted Triple-A Worcester skipper Chad Tracy.

They’ve taken 19 of their last 21 games via a never-say-die mentality that’s produced nine comeback wins, including Monday’s 6-5 classic over Baltimore that moved them within one victory of tying the franchise’s 15-game winning-streak record, set by Ted Williams’ 1946 Red Sox.

Red Sox World Series odds

The streak has left sportsbooks exposed, too.

A bettor who started with a $100 moneyline wager on the Red Sox and rolled over the entire payout into each of the club’s last 14 games would have turned it into $572,896, according to Bleacher Report.

Oddsmakers were initially hesitant to overreact to Boston’s surge, given that the streak began against cellar dwellers like the Angels and Mets. After sweeping the division-leading Rays and snapping the Orioles’ seven-game winning streak, the Red Sox have earned the market’s respect. 

Poor defense and inconsistent hitting had stymied the Red Sox through the spring.

But these wins have been fueled by contributions from every corner of the roster, creating a nightly carousel of heroes, whether it’s two-out RBIs from a pinch hitter, a timely defensive play or a clutch bullpen performance.

Caleb Durbin, who entered the year as a controversial replacement at third base, has emerged as one of baseball’s hottest sluggers. On May 25, he was hitting .163 and owned a single home run, but since then, he is mashing .304 with nine home runs. 

Aroldis Chapman #44 of the Boston Red Sox looks on during the ninth inning of the 2026 MLB All-Star Game at Citizens Bank Park on July 14, 2026 in Philadelphia, Pennsylvania. Getty Images

Willson Contreras is enjoying the best season of his 11-year MLB career, conjuring more contact power with 22 home runs — only two away from his career high. Even after a five-game suspension following a June 30 spat against the Nationals, Contreras still leads the team in RBI throughout the winning streak.  

Aroldis Chapman hasn’t yielded as one of the game’s all-time most prolific closing pitchers. He’s picked up eight saves in his 10 appearances since June 25 and is one away from tying Dennis Eckersley for the ninth-most all-time. 

The bullpen has been a full earned run better than every other team in baseball through the streak with a 1.15 ERA. Garrett Whitlock has posted 12 scoreless appearances, while Tayron Guerrero allowed his first earned run in 11 starts Monday.

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All of a sudden, trade chips like Chapman, Sonny Gray and Jarren Duran have all taken steep dips in Kalshi’s Players Traded market. 

With five straight games against division opponents ahead and 15 more within the AL East still slated afterward, Boston has plenty of opportunities to keep reshaping the standings and the odds.

Why Trust New York Post Betting

Sean Treppedi handicaps the NFL, NHL, MLB and college football for the New York Post. He primarily focuses on picks that reflect market value while tracking trends to mitigate risk.