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Five Losers of MLB's Offseason

Despite many teams going on a winter spending spree, baseball seems to be in a precarious spot.

Pitchers and catchers officially begin their preseason workouts this week, ending an eventful offseason where many teams improved their rosters heading into 2020. 

For all the winners of the winters, though, there are the offseason losers. These are the clubs that failed to make the necessary roster upgrades, the free agents who miscalculated their values and the aging players in the twilight of their careers whose services are no longer desired. Below are the five biggest losers this winter.

Houston Astros

Hard to come out a winner when a damning MLB investigation results in historic punishments and the eventual firing of the manager and GM.

Sign stealing aside, while MLB was conducting its investigation, the baseball world gathered in San Diego for the Winter Meetings in December. It was there that one of the Astros’ three aces from 2019 signed a record-setting nine-year, $324 million contract with the Yankees. Then, a day later, third baseman Anthony Rendon signed a seven-year, $245 million deal with the Angels, joining a lineup that already featured Mike Trout and Shohei Ohtani. The Astros lost the best pitcher on the planet and now will have to face that upgraded Angels offense 19 times this season. You can bet they'll face Cole once or twice, too.

Their division got better; they got worse. And they will have to deal with the aftermath of an enormous scandal, casting doubt on the authenticity of all they’ve accomplished these past few years–and everything they'll do going forward.

Boston Red Sox

What’s worse than your team firing its manager because of his role in orchestrating another team’s sign-stealing scandal? Trading away a home-grown superstar–the second best player in baseball–after days of public negotiations and months of speculation to save money.

Sure, the Red Sox were probably going to be without manager Alex Cora at least for part of this season anyway, but Mookie Betts was under contract for one more season. By unloading the $27 million contract of one of the best players in franchise history, one of the richest organizations in professional sports is choosing not to compete in 2020. That’s not good for the game. As Stephanie Apstein wrote last week when news of the trade first broke, “When the Red Sox traded Betts, they said two things to their fans: Maybe next year. And: Screw you.”

Oh, and let’s not forget, Manfred is expected to release the results of MLB’s sign-stealing investigation into the 2018 Red Sox sometime this week.

MLB Commissioner Rob Manfred

Despite a revival in free-agent spending that blanketed the sport in calm, Manfred's sport is in a place of turmoil. The Astros' historic sign-stealing scandal is still being unspooled; the Wall Street Journal reported Houston's front office was much more involved in the sign-stealing operation than the commissioner had disclosed.

On top of that, the lack of trust between the league and the MLB Players Association has not improved. Kris Bryant's lost service time grievance only stoked those flames. What's more, Minor League Baseball is revolting against MLB's plans to slash 42 affiliate clubs, there's never-ending skepticism of a juiced baseball, the game is bogged down by a slowing pace of play and declining attendance.

There will always be issues facing the sport, but this winter surfaced an extraordinary amount.

Nolan Arenado, Colorado Rockies

Arenado is a loser this offseason for the same reason he was a winner last winter—he signed an extension to be the Rockies’ third baseman until at least the end of the 2021 season. What a difference a year makes.

This time last year, Arenado was headed to spring training with the Rockies coming off consecutive postseason appearances and the acknowledgement that ownership would commit to building a sustainable winner. Then came a brutal 2019 season, a fourth-place finish and Arenado essentially asking to get traded. Dangling the face of the franchise is one thing. It happens (see: Betts, Mookie). But then the Rockies stopped fielding offers for Arenado after expressing a desire to trade him, prompting him to voice his displeasure to the team’s beat writers. The five-time All-Star said he felt “disrespected” by the Rockies. This situation is far from resolved.

Jacob deGrom, New York Mets

deGrom has won consecutive Cy Young awards and is one of the top five pitchers in baseball. How could he possibly be a loser? It’s all relative.

Before the 2019 season, deGrom signed a five-year, $137.5 million extension with the Mets, beginning in 2020. Had he not done so, the 31-year-old would have been a free agent this winter in a robust market for top-tier starters. Most likely, he could have signed for seven or eight years and made at least a quarter-billion dollars, more than what Stephen Strasburg got to re-sign with the Nationals. That’s a lot of money he left on the table to return to the Mets, the lovable yet dysfunctional organization that fired its new manager before spring training and last week botched an agreement to sell the team.

But, on the bright side, he could go down as one of the best players in franchise history. And maybe that’s worth the cost of any short term loss.