How Red Sox Completely Butchered Trade Deadline In Four Straight Seasons
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The Boston Red Sox should still make the playoffs this season.
With that said, they did not make it easy on themselves after a remarkably underwhelming performance at the MLB trade deadline.
BOSTON, MA - MAY 19: Craig Breslow chief baseball officer of the Boston Red Sox before the game against the New York Mets at Fenway Park on May 19, 2025 in Boston, Massachusetts.
BOSTON, MA - MAY 19: Craig Breslow chief baseball officer of the Boston Red Sox before the game against the New York Mets at Fenway Park on May 19, 2025 in Boston, Massachusetts.That's been the reality for four consecutive trade deadlines for the Red Sox. If they miss the postseason for the fourth consecutive season as well, they can point back to Thursday as a result.
Let's revisit how this became a running trend in Boston.
The Red Sox hovered outside of a playoff spot in 2022 when the trade deadline rolled around. Boston had a semblance of a path to the postseason, but it also had several expiring contracts that could've returned impact young players to benefit the organization's already improving farm system.
The issue was, Boston's chief baseball officer Chaim Bloom failed to pick a lane.
He bought and sold on the margins. He brought in additions in Tommy Pham, Eric Hosmer and Reese McGuire. Those moves didn't get the team any closer to October. On the other side, the one sell move Bloom did execute panned out well when he dealt veteran catcher Christian Vazquez to the Houston Astros for minor league bats Enmanuel Valdez and Wilyer Abreu. Valdez didn't work out and got flipped to the Pittsburgh Pirates last offseason, though Abreu is an impact player in Boston with streaky offensive production and won a Gold Glove in right field last season.
Abreu represents exactly what could've been for Boston if Bloom committed to a hard sell. What could the Red Sox have gotten for slugger J.D. Martinez? How about shortstop Xander Bogaerts, who walked for $280 million from the San Diego Padres that winter?
The confusing approach left Boston's clubhouse in an awkward spot with an inadequate roster that could not build on the previous season's momentum that brought the Red Sox to the American League Championship Series. Instead, Boston missed the postseason and stayed over the luxury tax.
How about 2023 and 2024?
Once again, those resulted in marginal results under two different executives between Bloom and Breslow. The team sat in similar spots around .500 in both seasons as July came to a close.
The 2023 deadline brought infielder Luis Urias, who will only be remembered for when he hit two grand slams on back-to-back pitches in an otherwise forgettable 22-34 stretch to end the year.
Boston earned the right to add last year, which for Breslow apparently equated to dishing off prospects who would've been unprotected in the Rule 5 Draft for the following players who regressed upon arrival with the Red Sox: catcher Danny Jansen, starting pitcher James Paxton (injured in third start), pitcher Quinn Priester in a prospect swap and rounded out with relievers Lucas Sims and Luis Garcia.
Once again, not enough to show for and another playoff absence.
That brings us to this time around. Boston entered the trade deadline in control of the second wild-card spot in the American League. Breslow's to-do list included bullpen help, a frontline starter and a first baseman with Triston Casas still out for the season.
Steven Matz adds another solid arm to the leverage group for the Red Sox with All-Star closer Aroldis Chapman, Garrett Whitlock, Greg Weissert and Justin Wilson. Boston also added Dustin May, a once-electrifying young arm who no longer had a place on a championship roster for the Los Angeles Dodgers.
That's all Boston had to show for when Thursday's 6 p.m. ET deadline expired. So much for aggressively buying less than two months after the season-altering trade of franchise star Rafael Devers to the San Francisco Giants. No first baseman and no frontline starter.
The latter sparked other frustrations in the inability to close a deal for Minnesota Twins frontline starter Joe Ryan, as best described by The Athletic's Ken Rosenthal.
"Epic fail," Rosenthal said on "Foul Territory" Thursday night. "It comes off an epic fail at last year's trade deadline with Craig Breslow and this was an epic fail as well. They met the same issue that the Cubs ran into. Joe Ryan is another starting pitcher who wasn't traded, but my understanding is any talks they had with the Twins were feeble at best. They didn't come at them hard. The Red Sox are one of many teams that uses modeling and tries to figure out what the best values are and it's all about efficiency and getting the best deal and this, that and the other thing.
"At some point, you've got to fire. It's the same thing we're saying with the Cubs. They did not even address first base, which I know they've gotten decent work out of Romy Gonzalez and Abraham Toro, but my goodness. That was a position where they had to act. They tried for Eugenio Suarez and they tried with the idea of playing him at first base. Didn't get him. Didn't get a starter other than Dustin May, who has not been a very successful starter for the Dodgers. In their bullpen with Steven Matz, he's a swing guy, he can be effective. But my goodness, they needed more. This is a team that is on the rise."
Clashing reports leave some doubts on the status of the offers back and forth between the Red Sox and Twins. What is not in doubt is that with the exception of the four-player return last December to land ace Garrett Crochet, the Red Sox have shown a collective failure for a half-decade to make decisive trades for impact players.
That part is really puzzling, because when have the Red Sox ever gotten burned for what they traded away for stars?
The only player, without a doubt, in the last 25 years that the Red Sox can point to who ever amounted to legitimate MLB production is Hanley Ramirez. Boston traded the infield prospect to the then-Florida Marlins in 2005 for Josh Beckett and Mike Lowell.
Sure, Ramirez hit .300 with three All-Star selections as a Marlin, though the Red Sox got exactly what they needed in 2007. Beckett won 20 games that year with a 1.20 ERA in 30 postseason innings while Lowell emerged as the World Series MVP to help Boston win its second championship in four seasons. Those two players also combined for four total All-Star selections in a five-year window for the Red Sox.
Boston also signed Ramirez back years later entering 2015 and he posted a .423 batting average and a 1.021 OPS over two postseasons for the Red Sox.
The point of that historical context? Prospects rarely pan out and the Red Sox have a history of winning daring deals.
They won the deal to get Beckett and Lowell. They won the deal to get Chris Sale. The list goes on and on.
Holding onto Roman Anthony and Marcelo Mayer in recent years is understandable. Otherwise, there's no historical context in Boston's memory that could ever validate this gunshy approach that cost the Red Sox several chances at playing baseball in October.
Even the reality of needing to trade an outfielder like Jarren Duran or Abreu should not have stood in the way of acquiring an arm like Ryan to bolster a playoff-hopeful starting rotation.
The Red Sox now face the task of ending this narrative from the last three years: Boston mismanages the deadline, the morale slumps and Boston plummets over the final two months.
Boston is a combined 73-97 after the trade deadline since 2022. That should tell you everything you need to know. Now, the reality is that the Red Sox do have a better roster this time around by a significant margin. There's a different DNA with star players and different leadership in the clubhouse.
Anthony, Crochet and Alex Bregman weren't there to help in years past. They could be the reason the Red Sox ultimately overcome another disastrous trade deadline performance from their baseball operations staff.
The Red Sox should still be a playoff team, but the lack of a splash just handcuffed how far Boston can go while several other American League contenders improved including the New York Yankees, the Detroit Tigers, the Houston Astros and the Seattle Mariners.
At some point, the trend must end or a massive shake-up needs to happen at Fenway Park. It's up to the Red Sox to decide that fate over their final 52 games.
More MLB: Phillies Boss Defends No. 1 Prospect Trade Decision After Deadline Moves
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