Boston Red Sox Should Be Trade Deadline Sellers

· Yahoo Sports

There may not be a bigger disappointment across baseball in 2026 than the Boston Red Sox, who enter Friday’s series opener in Seattle fresh off a new low point of the season - a home sweep at the hands of the Toronto Blue Jays to put Boston a season high 14 games below .500. As trade rumor season kicks into full swing, the Red Sox have just a 9.5 percent chance to make the playoffs according to Fangraphs. It’s time for Chief Baseball Officer Craig Breslow and the rest of the front office to shift their attention to being deadline sellers. 

At 29-43, the Red Sox are on pace to finish the season 65-97, their worst record in a 162-game season since 1965. They would need to undergo a remarkable turnaround to make their first consecutive playoff appearances since 2017 and 2018. Since the inception of the third wild card in 2022, the average win total of third wild card teams is 87 wins, meaning Boston would need to go 58-32 over their final 90 games of the season to be in line with the historical norm. To put that into perspective, the Red Sox would have to play their final 90 games at a 104-win pace over a full 162-game season. 

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Boston closer Aroldis Chapman has been one of the best closers in baseball since joining the Red Sox ahead of the 2025 season. He figures to be the top relief name on the market if Breslow does choose to sell ahead of the August 3 deadline. © Eric Canha-Imagn Images

Winning 104 games in the regular season is a tall task for even World Series favorites, let alone a team that will enter play on Friday with the second fewest runs in baseball through 72 games, which the Red Sox will do. 

Unfortunately, even in an incredibly mediocre American League, it is more likely than not that the Red Sox have already dug themselves a hole too deep to dig out of in 2026. 

Management softening their stance on selling? 

In the wake of the firings of former manager Alex Cora and five members of the major-league coaching staff, both Breslow and team president Sam Kennedy remained steadfast in their belief that this was a playoff team. That stance has softened in recent days, with Kennedy opening up about the idea of selling. 

“Let’s be honest, unless things change dramatically, we may have to pivot here from what our initial planning was. It just wouldn’t be responsible to do otherwise,” Kennedy told WEEI’s The Greg Hill Show last Thursday. 

He followed up those statements on WEEI with an appearance on NESN’s pregame show ahead of Wednesday night’s loss to Toronto. “You have to do what’s in the best interest of the organization,” Kennedy told Tom Caron. “And that’s what we’ll do if we’re in that position, but it’s brutal and truly unthinkable given the expectations,” he continued.

While unthinkable, the Red Sox, through 72 games, have proven that they do not have what it takes to make the postseason. It is well within the best interest of the organization to sell off key pieces like closer Aroldis Chapman, starter Sonny Gray, and maybe even an outfielder to finally clear the outfield logjam and gear up for the 2027 season. 

The MLB trade deadline is Aug. 3 at 6:00 p.m. ET. 

Meanwhile, Boston will look to snap its four-game losing streak on Friday night in game one of a six-game West Coast trip, which gets underway in Seattle. Ranger Suarez (2-3, 3.21 ERA) gets the start for the Red Sox opposite Bryce Miller (3-0, 1.54 ERA) for the Mariners. First pitch from T-Mobile Park set for 10:10 p.m. ET.

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