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Which MLB Team Had The Most Disappointing Offseason In 2020?



This is one of 10 burning questions in our 2020 MLB season preview. To see all of our bold predictions, click here. All answers to the question are from Baseball America’s editorial team.


Ben Badler: Mets. Mets fans thought they were one step closer to escaping the worst ownership in the game, only to get kicked in the teeth yet again.

Carlos Collazo: Astros. Houston essentially wrote the perfect script for how to have the worst offseason in baseball—or any sport. They followed one PR disaster after another before losing the World Series, became the centerpiece of one of the biggest scandals in baseball history and simultaneously turned into the most hated team in baseball and soured a historic 2017 World Series championship. Oh yeah, they also lost Gerrit Cole to their American League rival. Bravo.

JJ Cooper: Red Sox. While Houston’s sign-stealing scandal got most of the attention, Boston faced its own investigation as well, traded away the best player its produced in a generation, brought in no significant reinforcements and moved years away from its next serious playoff run.

Matt Eddy: Astros. Losing Gerrit Cole to the American League rival Yankees wasn’t even the biggest calamity to befall the Astros in the offseason. Houston’s sign-stealing scandal disgraced its players, called into question the club’s accomplishments and cost general manager Jeff Luhnow and manager A.J. Hinch their jobs.

Kyle Glaser: Cubs. The Astros’ and Red Sox’s debacles took the headlines, but the Cubs’ offseason was nothing to be proud of in its own way. The North Siders badly needed to upgrade their outfield, bullpen and back of the rotation, and did none of it. They still have the talent to contend in the National League Central, but they could have done more and willingly chose not to.

Joe Healy: Astros. They started the offseason losing Gerrit Cole, which now seems like it happened roughly a decade ago, and then things went downhill from there. The team might play with a chip on its shoulder in 2020, but this was the type of offseason that’s going to stick with the franchise for years to come.

Josh Norris: Once again, I’m going to cop out and say MLB had the worst offseason. Last offseason, the league shot itself in the foot with its free agency freeze out. Now, a sign-stealing scandal led to the firing of two of the last three World Series-winning managers and a general manager and has raised questions about the integrity of the sport itself. Throw in an assistant general manager fired for misogynistic comments during the postseason, the looming contraction of dozens of minor league teams and a round of contentious Collective Bargaining Agreement negotiations on the horizon, and it all adds up to one of the most toxic offseasons in recent memory.

Chris Trenkle: Astros. Not only did Houston fire its GM and manager for their roles in the sign-stealing scandal, but Gerrit Cole left town for the Bronx and Will Harris, coming off an excellent season as a high-leverage reliever, signed with the Nationals. The only win for the Astros is the offseason is mercifully over.

Luisrobert Eloyjimenez Ronveselygetty

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