Which MLB teams had the worst offseasons? Red Sox, Astros, Cardinals make list of disappointing winters

With pitchers and catchers reporting this week for spring training, it's time to shift into preseason mode. Part of that transition entails recapping what happened over the winter, including identifying which teams had the best offseasons, and which teams had the worst offseasons. For want of a better transition: this piece will concern itself with the worst offseasons. (The best offseasons piece will follow Friday, ending the week on a positive note.)

Before getting down to business, let's be clear about a few things. Determining the worst offseasons is a subjective matter; not everyone is going to agree with who we included or excluded. For example, the Chicago Cubs could be on this list. We didn't put them on here because we think there's justification in not trading a core piece (especially given the less-than-expected return on Willson Contreras and their chances of making the postseason). We take no offense if you think this or that team should be on here instead of someone else.

We did try to provide additional context for our picks by separating the teams into two categories, based on their activity level: you have the movers, or those who participated in a meaningful way this winter, and the non-movers, or those who were dormant. It's possible to have a good offseason either way, depending on the greater circumstances at play.

One last note, to avoid possible confusion: we're not saying these teams will have bad seasons. In some cases, we're saying they're likely to have good seasons, and that a little more oomph this winter would have improved their chances of having a special year.

Movers

Red Sox

Recency bias dictates we have to start with the Red Sox, who remain under investigation by Major League Baseball for their improper use of technology during the 2018 season. Despite winning the World Series that fall, Boston will enter this season with a different pair at general manager (Chaim Bloom) and manager (Ron Roenicke). Dave Dombrowski was fired last September, and Alex Cora in January due to his involvement in the Astros' sign-stealing mess.

That sequence of events on its own would have left the Red Sox and their fans in a dour mood. To make matters worse, the team then traded Mookie Betts, the franchise's homegrown MVP, as well as David Price and cash considerations for an underwhelming package -- all to save money. (We won't even touch on how Boston was behind the trade's lengthy, agonizing delay.) In return, the Red Sox landed Alex Verdugo, Jeter Downs, and Connor Wong

Verdugo could break out and become an All-Star-caliber outfielder, especially if he trades some of his contact for more power, but other teams were (and have been) unwilling to touch him due to significant makeup concerns. Downs is a polarizing prospect. He does a little bit of everything, and could become Boston's starting second baseman as soon as 2021 if all goes well. There is a chance his lack of a carrying tool causes him to fall short of that projection. Wong is a versatile defender with experience behind the plate and at second and third base. There's too much swing-and-miss in his game to envision him becoming more than a reserve.

Each of those players could contribute in some way to future Red Sox teams, but collectively they don't seem to be worth the second-best player in baseball -- let alone an above-average starting pitcher, and half of the money owed to him. Keep in mind, projection systems are high on this Red Sox team, pegging them as a playoff contender. The pitching looked rough on paper, and it's possible they would've fallen well short of expectations, again. Still, it would've been nice to see Bloom try to salvage what he could, not hit reset just because.

In less important news, the Red Sox seem to have miscalculated by tendering a contract to Jackie Bradley Jr. He was expected to be traded, but that hasn't yet happened and it's unclear if it will before the trade deadline. Bringing back Mitch Moreland is fine; signing Martin Perez, Jose Peraza, Kevin Plawecki, and possibly Kevin Pillar is fine. The Red Sox will probably hit on one of their low-level additions, too -- be it Austin Brice, Trevor Hildenberger, Jeffrey Springs, whomever. None of this stuff really matters, because Boston isn't that worried about 2020, anyway.

Bloom is well-regarded within the industry, and in due time he'll probably build a good team of his own. Lord have mercy, though, because this has been a brutal introduction to his new gig.

Brewers

Say this much for David Stearns: he kept himself busy this offseason. He added three or four pieces to the lineup, depending on the day, as well as three members to the rotation. He did so while reducing payroll -- about $25 million from last Opening Day -- and without flattening their playoff hopes. Basically, Stearns' offseason was the real-life embodiment of this tweet:

We're putting Milwaukee here for a few reasons. Executives working within a finite budget is part of the game, but jeez are the optics horrid. The Brewers were a win away from the pennant in 2018, and a fluke misplay away from the Divisional Series last fall. Was this really the time to have an offseason defined by cost-cutting measures? Beyond that, Stearns did well enough to maintain some competitive aspirations, yet the floor on this squad seems lower than before.

The Brewers opened the offseason with an aggressive slew of non-tenders, and by trading away staff anchor Zach Davies. Part of the return there was Eric Lauer, who, along with free-agent additions Brett Anderson and Josh Lindblom, will fill out the rotation around Brandon Woodruff and Adrian Houser. Regardless of what one thinks about Lauer, both Anderson and Lindblom are risky quantities. Anderson is reliant on pitching to weak groundball contact, making him a questionable fit for a team who isn't likely to field a single plus defender on the infield. He's also prone to injury, having started fewer than 20 times in three of the last four seasons. Lindblom, meanwhile, is returning from overseas. It's to be seen how his finesse arsenal plays multiple times through the order against big-league hitting. 

The Brewers' pitching staff won't have the benefit of working with Yasmani Grandal anymore, either. Instead Stearns downgraded to Omar Narvaez, a good hitter and poor framer. The Brewers courted risk with most of their other offensive additions. Avisail Garcia and Eric Sogard had uncharacteristically productive seasons in 2019. Their underlying measures don't indicate the pair will continue to perform to that level, yet the Brewers guaranteed them $24 million. (Not a lot of money, except against the backdrop of Milwaukee cutting payroll.) Jedd Gyorko, who scouts thought was toast last season, and Ryon Healy will see burn against lefties. 

Acquiring Luis Urias from the Padres was the closest thing the Brewers made to an upside play. Urias will miss time due to injury, and his bat hasn't translated so far against big-league pitching. Additionally, it's unclear if he can handle the rigors of shortstop. The Brewers have had success with other unconventional defensive alignments, thanks in part to Craig Counsell and the front office's defensive positioning, so it'll be interesting to see if they can make it work. Banking on Justin Smoak's ball-tracking metrics leading to better surface-level statistics should pay off.

The Brewers have a good front office, and it seems obvious that their hands were tied by self-imposed restraints from above. Maybe Stearns and crew will have a higher batting average than seems likely. If so, they should find themselves in the thick of the postseason race. If not, the Brewers will be taking a step back at an inopportune time, given their recent momentum.

Non-movers

Cleveland

You can repurpose that final paragraph on the Brewers here. Cleveland's front office is quite good, but the team did almost nothing of note this winter, save for signing Cesar Hernandez and trading away Corey Kluber without getting a ton back. (Yes, yes, Emmanuel Clase is going to be a monster.) We would've liked to have seen Cleveland sign at least another outfielder, a Kole Calhoun or Corey Dickerson type, and show a greater sense of urgency as the Francisco Lindor era winds down. Cleveland could make us look stupid by living up to its reputation as a player-development machine, but even then, why rely on that possibility and that alone?

Cardinals

The Cardinals won the National League Central last season, and could win it again this year. They didn't do much to help their cause, save for signing left-hander Kwang-Hyun Kim and retaining backup catcher Matt Wieters. John Mozeliak permitted Marcell Ozuna to walk to Atlanta, and traded Jose Martinez and Randy Arozarena (albeit in a good deal, value-wise, for Matthew Liberatore). The Cardinals should be able to add Dylan Carlson to their roster at some point this season, which is a plus, but here's a somewhat concerning stat: the Cardinals figure to start four players who are 32 or older; the other NL division winners, the Dodgers and Braves, will start two such players … combined. Age is going to become a factor at some point, and we would've liked to have seen the Cardinals steel themselves against the potential decline that half their lineup could experience.

Rockies

The Rockies have signed one player, Jose Mujica, to a big-league contract all winter. They're coming off a 71-win season. They didn't wave the white flag by trading away Nolan Arenado, but they did enrage him to the point where a parting seems likely. The Rockies will probably win more games than they did last season, but there's a chance this snowballs into a mess, too.

Orioles

Adding marginal wins to a team that will be fortunate to avoid 100 losses might seem pointless, but have you looked at this roster? Things are going to get worse if and when they trade Trey Mancini and Mychal Givens, among the few others left standing from the Dan Duquette era. We would've liked to have seen a few more signings akin to Jose Iglesias, just to give the Camden Yards faithful a slightly better product to enjoy during an otherwise cruel summer. 

Astros

No codebreaking necessary. 

CBS Sports Staff

R.J. Anderson joined CBS Sports in 2016. He previously wrote for Baseball Prospectus, where he contributed to five of the New York Times bestselling annuals. His work has also appeared in Newsweek and... Full Bio

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