The Boston Red Sox front office remains in the market for relievers and right-handed bats as it continues a busy offseason thus far after some key trades and free agent acquisitions.
There is still work to be done, and in time, they will be graded based on the contributions of the likes of Garrett Crochet, Walker Buehler, and others. But for now, here's a look at the 10 worst moves made by the Red Sox over the past decade.
10 worst Red Sox offseason moves of the last 10 years
Feb. 11, 2020 - Mookie Betts and David Price traded to Dodgers for Connor Wong, Jeter Downs, and Alex Verdugo
This ranks not only as one of the worst trades in Red Sox history but in MLB history as well. The Red Sox parted ways with a top-three player and a pitcher for whom they overpaid dearly. Their return was underwhelming: an overrated outfielder who has since been traded to the Yankees as a double-agent to destroy that clubhouse, a serviceable catcher, and a player who most recently played in Japan but has a cool name.
The fact that the team didn’t do its best to make Betts the face of the franchise and, when that failed, gave him away for the equivalent of a bag of used baseballs remains shocking and Red Sox Nation still isn't over it.
Nov. 25, 2014 - Agreed to terms with Pablo Sandoval on a five-year contract worth $95 million and Hanley Ramirez on a four-year contract worth $88 million
This will always be a day of infamy in Red Sox history. On the same day, the team signed two supposed superstars, each of whom would do their part to destroy team chemistry in their tenures in Beantown.
Sandoval must have found the North End food to his liking and quite literally ate his way out of town. He was never equipped for this kind of scrutiny and was paid far too much money for what was a solid role on a World Series team in San Francisco.
Ramirez hit all of 78 home runs in his three-plus years for the Sox and never effectively made the shift to left field as the team promised when they traded for him. He was a malcontent at various points and was released during the run to the World Series in 2018.
Dec. 15, 2022 - Agreed to terms with Masataka Yoshida on a five-year contract worth $90 million
Can we get a do-over? Yoshida came to Boston billed as an RBI machine that could compete for batting titles and rarely struck out. He’s instead been an overpriced, poor-fielding, slow-footed outfielder with marginal pop. The Red Sox would love to trade him, but there just doesn’t seem to be much of a market for high-priced designated hitters who have never hit 20 home runs. Go figure. He remains the gift that keeps on giving as the team struggles to find him a new home.
March 23, 2019 - Red Sox sign Chris Sale to a five-year, $145 million extension
For years, the Red Sox brass fed us the line that they were not going to overpay starting pitchers closing in on 30 because of diminishing returns. We swallowed it when they let Pedro Martinez walk, we tolerated it when Jon Lester left town, and were seemingly prepared to do the same with Chris Sale.
Inexplicably, they gave Sale a massive extension and watched it blow up in their faces. Hmmm, which other impending free agent could Boston have used that money for? The 2018 MVP? Nah, that’s silly talk. How did Sale reward the Red Sox's about-face? He won 17 games over the next five seasons and made a grand total of 56 starts.
March 23, 2022 - Red Sox sign Trevor Story to a six-year, $140 million deal
The Red Sox let Xander Bogaerts walk after the 2022 season after they dropped out of a competitive bidding war when the price got too steep. Boston signed the veteran's replacement before he even left when it inked former Rockies star shortstop Trevor Story to a six-year deal.
Story has yet to play 162 games in TOTAL throughout three seasons in Boston. He’s shown flashes of his former self with his glove and at the plate, but his season high in games played was his first year, with 94. Since then, he’s played a combined 69 games. As he enters his mid-30s, surely he’ll be playing 140+ games a year, right? Right?
Dec. 4, 2015 - Red Sox sign David Price to seven-year, $217 million deal
Remember, the Sox aren’t in the business of signing 30-year-old pitchers to long-term deals but, oh wait, David Price was available? At 30, Price had already logged a lot of miles on that arm but the team plowed ahead. Price would win 46 games over five seasons in Boston, which did include a memorable run in the playoffs in 2018. Still, he was extremely thin-skinned, opted out of the 2020 season, and never produced a season worthy of his hefty contract.
Feb. 17, 2021 - Red Sox acquire Ronaldo Hernandez and minor league Nick Sogard from Tampa Bay in exchange for Jeffrey Springs, Chris Mazza and undisclosed money
Sogard was a modest contributor to last year’s team while Hernandez has never played a game above AAA. Mazza is now out of baseball, and Springs was converted to a full-time starter by the Rays. Springs won nine games with a 2.43 ERA in 2022 before injuring himself in each of the last two years. He is set to return this season and this deal could move up the list if he returns to form. Injuries have spared the Red Sox more egg on their face from this offseason move.
Dec. 30, 2023 - Red Sox acquire Vaughn Grissom from the Atlanta Braves for Chris Sale and cash considerations
Sale makes his second return to the list after his deal with the Braves last year. It was certainly time for him to move on but Boston's return hasn't panned out yet. Grissom played a total of 31 games for the Sox and battled injury and illness that saw him drop a ton of weight and, with that, much of his pop. Sale? He won the NL Cy Young Award with a record of 18-3 and an ERA just above 2.00.
Jan. 3, 2024 - Red Sox agree to terms with Lucas Giolito on a one-year contract with an option for 2025
The jury is still out on this deal, and Giolito could turn this from a negative into a positive with a solid year in 2025. Still, he deserves to be on this list, considering that the Red Sox made this signing one of their primary moves last offseason. He would've been the team's only veteran starter, and then UCL surgery shut him down for the season. Hopefully, he’ll be motivated to become a solid middle-of-the-rotation pitcher this year.
Oct. 25, 2019 - Red Sox hire Chaim Bloom as Chief Baseball Officer
In retrospect, it appears as though Bloom was hired just to be the scapegoat for the Betts trade. He also clearly had an edict placed on him to spend carefully and return the farm system to some semblance of respectability. The farm system has improved, but the Red Sox are not a small market team and should operate in a world where they can both replenish a farm system and improve the everyday roster. Bloom didn’t do both of those things and was ultimately the fall guy for the Red Sox. Perhaps Bloom will someday reveal what was going on behind the scenes, but for now, his hiring will represent an organizational failure.