The 1961 Philadelphia Phillies lost 23 games in a row. The 1988 Baltimore Orioles started 0-21. The 2024 Chicago White Sox dropped 21 straight in July on their way to a record of 121 losses. Every few years, one team manages to make history in the wrong direction.
So, who gets that dubious honor in 2026?
Kalshi is running a market on exactly that question: "Longest 2026 regular season losing streak?" and one team is sitting at the top by a wide margin.
New York Mets Losing Streak: Why They Are the Market Favorites
New York entered 2026 carrying one of the most expensive rosters in baseball, a payroll north of $375 million. The season started reasonably well… until it didn't.
Beginning April 9, the Mets dropped 12 straight games. Francisco Lindor acknowledged the weight of it: "We're all very aware of it," he said during the skid. By the time it ended, New York was 7-16, the worst record in the majors.
The slide had a clear culprit. Juan Soto missed 15 games with a quad strain, and the offense cratered. During the streak, the Mets scored fewer than two runs per game. Without Soto, they ranked last in MLB in runs scored. They also lost six games they had led at some point, a pattern that pointed to deeper problems in the bullpen. Closer Devin Williams, who had been sharp through April 7, gave up seven runs over his next 1⅓ innings.
Kalshi has the Mets as the top pick at 69% to end up with the season's longest losing streak. It's a significant gap from the next candidate.
Colorado Is the Other Team Worth Watching
While the Mets bring the high-profile drama, the Colorado Rockies are mounting a very real challenge of their own, sitting in second place with a 48% probability on Kalshi. Denver's campaign has been a relentless uphill battle.
Following a June loss to New York, the Rockies fell to a staggering 9-50, marking the longest any team in baseball history has ever taken to secure their 10th victory. That historic slump wasn't the result of just one isolated cold streak; within the first two months alone, Colorado endured four separate eight-game slides, doubling the number of such streaks they had recorded over the previous five seasons combined.
The franchise's all-time low-water mark for consecutive losses stands at 13, a record set back in 1993. At this current pace, however, that benchmark looks highly vulnerable long before September arrives.
Longest Losing Streaks in MLB History: Can Anyone Break the Record?
The modern-era record is 23 games, set by those same 1961 Phillies. Reaching that number would require a truly historic level of dysfunction. That said, the 2024 White Sox, who set the current record for losses in a season, did put together a 21-game skid, so it's not impossible for a bad team to get there.
Whether it's the Mets running out of roster depth, the Rockies extending their already-ugly losing sequences, or some other team collapsing quietly in the background, Kalshi's market suggests the answer will come from one of two zip codes. Given New York's recent history and the pressure of carrying a massive payroll through a brutal slump, the Mets are the ones with the most to prove… and the most ways to keep losing.
