Jon Lester of the Boston Red Sox
If sitting 12 games under .500 in mid-June with your two best players injured isn’t a sign to sell at the trade deadline, I’m not sure what is.
The Red Sox have to pick a lane to properly run the trade deadline on Aug. 3. That’s something Boston has failed to do in each of the last four seasons with catastrophic decisions at each one. The lone positive deal came back in 2022 when Chaim Bloom flipped Christian Vazquez to the Houston Astros in the deal that brought Wilyer Abreu to Boston.
With several veteran pieces that would be ready to help out a true contender, the Red Sox have the assets to be desired sellers in under two months. Whatever Boston does, the front office cannot follow the blueprint of the last few deadlines, both of which were disastrous.
Instead, to find their plan for the first Monday in August, the Red Sox need to jump into their time machine and land in 2014. If your team is bad, make it fun and be active instead of sitting around with no efforts to change.
Boston set a franchise-record with four deals on deadline day with multiple splashes that swapped stars and also laid the groundwork for a championship core.
The Red Sox started a few days early when they traded right-hander Jake Peavy to the eventual World Series champion San Francisco Giants. Quite the two seasons for the starter to bring home a pair of rings at the end of his career.
Then on July 31, the Red Sox made a seismic move around the sport when they ended an era and traded ace Jon Lester to the Oakland Athletics along with Jonny Gomes for Cuban slugger Yoenis Cespedes. The power-hitting outfielder only lasted the rest of the season in Boston before he was flipped in the offseason for right-hander Rick Porcello to the Detroit Tigers (they should’ve kept Cespedes here longer, but that’s a story for another day).
Ben Cherington was far from done that day. Next went John Lackey and a prospect to the St. Louis Cardinals for Allen Craig and Joe Kelly. Then came two in-division trades with Stephen Drew going to the Yankees in a swap for Kelly Johnson. Finally, the Orioles got a premiere reliever in Andrew Miller while the Red Sox got a future staple of the rotation in young lefty Eduardo Rodriguez.
That’s how you do the deadline in a losing season. Take advantage of dealing assets and bring back valuable returns for your next winning core.
It would be inexcusable for the Red Sox to not do the same this season. Move Sonny Gray. Move Aroldis Chapman. Move bullpen arms for a price. Listen on the outfield and catching depth.
The Willson Contreras decision is more complicated with more control past 2026. If a team blows them away, maybe there’s a deal to make knowing how much he can raise the ceiling of another lineup entering October. Otherwise, Boston would benefit from having him stay at first base, especially with the mystery of Triston Casas not showing many answers for his future.
Learn from the past, just not the recent past. The Red Sox should sell.
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