In 2014, the disappointing Red Sox had a massive selloff at the trade deadline. Are the 2026 Sox headed in that direction?
For the Red Sox, 2026 represents a case of history repeating.
The dynamics are almost eerily familiar: A team coming off a “restoration” year and believing that an emerging young core had created a title window. An offensive collapse that occurred in no small part because of a power deficiency, and because unestablished big leaguers weren’t ready. A waste of pitching excellence. The early realization that anticipated contention could give way to a massive selloff.
The Red Sox are experiencing those elements in 2026. They experienced them in 2014, too.
In 2014, the Sox were coming off an improbable championship run in 2013. The emergence of Xander Bogaerts in the playoffs gave them a star in the making. Promising young big leaguers Will Middlebrooks and Jackie Bradley Jr. stood poised for steps forward. And there was more promise on the horizon with prospects Mookie Betts, Christian Vázquez, and more.
That wave, combined with veterans such as David Ortiz, Dustin Pedroia, Jon Lester, John Lackey, Shane Victorino, Mike Napoli, and others (including veteran reliever Craig Breslow, now the Sox’ chief baseball officer) led to expectations that the Sox could reside atop the American League East for years. Instead, they discovered the porous boundary between greatness and gruesomeness, and how quickly title hopes can turn to a roster shakeup.
Middlebrooks, now an analyst on WEEI’s Red Sox broadcasts, recognizes the similarities.
He was then entering his third big league season, optimistic he’d solidify himself in the lineup for years to come. He remembers the initial surprise of a poor start, which quickly mushroomed into alarm.
“I hate to say this and hate talking like this, but [there is an echo in] just the consistency of finding ways to lose games offensively,” said Middlebrooks. “That starts to pile up.”
The Sox had let free agents Jacoby Ellsbury, Stephen Drew, and Jarrod Saltalamacchia walk, and didn’t backfill with established veterans beyond A.J. Pierzynski. Instead, they made a massive bet that emerging young talent surrounded by the right veterans would be able to compete for another title.
Instead, a lineup that led the big leagues in slugging in 2013 and finished sixth in home runs dropped to the bottom 10 in both categories in 2014. It was jarring for the front office, which eventually concluded that it had placed unrealistic expectations on young players, and for the young players themselves.
Middlebrooks suffered a calf injury in the first week of the season, struggled when he returned, then suffered a broken finger that sidelined him by mid-May. Poor health and poor performance created a mind-set that made it harder to escape his funk.
At different times that year, Middlebrooks, Bogaerts, Betts, and Bradley appeared lost. Middlebrooks wonders if similar dynamics exist with the current young Sox, particularly projected mainstays Roman Anthony, Marcelo Mayer, Caleb Durbin, and Carlos Narváez.
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“The human aspect of the negative thoughts is, ‘Am I going to lose my spot? … Am I going to be productive enough to stay in the lineup and be the guy they expect me to be?’ ” said Middlebrooks. “[Those thoughts are] just an extra weight. This game’s hard enough when you’re going well and everything feels good and you’re swinging the bat well. It’s really hard when you’re trying to solidify yourself.”
In 2014, instead of solidifying themselves and their team, the young players saw their funks deepen — and most of the veteran hitters suffered injuries or played well below their norms. The result was a shocking offensive struggle, too extreme even for elite pitching by Lester, Lackey, and others to overcome.
The Sox had losing records every month. The entropy of the early-season slide soon became obvious, and irresistible.
“You kind of just watched the first month go by, and it’s like, ‘OK, bad month.’ Second month goes by, and you’re like, ‘[Shoot], we’ve got to really turn it on, or we’re going to lose some big names, and this team’s going to look a lot different,’ ” Middlebrooks said. “It definitely changed the vibe of the clubhouse as far as hanging out with the veterans, because the veterans’ whole mood changed because they knew what was coming.
“You start getting to the point where this [2026] team is right now, where you’re a month out from the trade deadline, and the clubhouse kind of goes quiet as far as the camaraderie, going out to team dinners, because everybody — especially the vets — starts to think, ‘I’m going to have to uproot everything, because I know contractually where I’m at, and I’m probably going to end up somewhere else.’ That’s got to be the thought process in the clubhouse here. It’s got to be really similar.”
Middlebrooks offered the observation on Thursday morning. Hours later, after the Sox lost to the Blue Jays, veteran Isiah Kiner-Falefa confirmed how the current team’s outlook echoes that of the 2014 club.
“It’s time to go on a streak,” Kiner-Falefa said, “or we’re going to be having new players in this locker room.”
The 2014 team engaged in a massive selloff, with Lester, Lackey, Jonny Gomes, Andrew Miller, and Drew (who’d been re-signed after Middlebrooks landed on the injured list for the second time) getting dealt. The Sox finished 71-91, but their struggles afforded Bogaerts and Betts the chance to catch their breath and achieve success by the end of the year.
Meanwhile, the deadline additions of Yoenis Cespedes (acquired for Lester and Gomes, eventually dealt for Rick Porcello), Joe Kelly (acquired along with Allan Craig in the Lackey deal), and Eduardo Rodriguez (Miller) paid eventual dividends in building a contender.
Still, the process to get to that payoff was painful, and there are plenty of warning signs that the 2026 campaign will follow a similar course.
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