Yankees must love Red Sox stuck in the middle with trade deadline plans

New York Yankees fans have surely enjoyed every second of the Boston Red Sox's nightmare 2026 season. This is the worst Red Sox product in multiple decades, and it's basically a foregone conclusion that Boston will operate as a seller at the trade deadline.

The most likely goner in a Red Sox uniform is closer Aroldis Chapman. ESPN's Buster Olney recently gave it a 90% chance that Chapman will be dealt, though it certainly won't be to the Yankees.

Jarren Duran and Sonny Gray are other trade chips for Boston. And what about first baseman Willson Contreras? Contreras is having the best offensive season of his MLB career, making this a perfect "sell-high" opportunity for Craig Breslow and Boston's disreputable front office.

The Red Sox are going absolutely nowhere and should be putting all of their players above 30 years old with any value on the block (Contreras included). Nonetheless, there's been some pushback about Boston selling Contreras, and the Red Sox might be conflicted.

Ken Rosenthal just argued that the Red Sox shouldn't trade Willson Contreras

Rosenthal's assertion that the Red Sox "never take a full step back" was full of irony during a campaign in which Boston is on track for its worst winning percentage in over 60 years.

The Red Sox have taken multiple steps back in 2026, and with Contreras being 34 years old there's no reason to make him untouchable. Isn't Boston's plan to build around 22-year-old Roman Anthony, 25-year-old Ceddanne Rafaela, 26-year-old Wilyer Abreu, and 27-year-old Garrett Crochet? Aren't Connelly Early and Payton Tolle both under 25 as well?

That's why it makes no sense for the Red Sox to factor Contreras into their long-term blueprint. He's had a heck of a year and he's a great right-handed bat for Fenway Park. But the timing is off. By the time all of the aforementioned players are hitting their stride together, Contreras will be close to retirement.

Unless the Red Sox think they are going to miraculously turn things around by this time next year and suddenly turn into a contender, there's no reason to grip tightly to Contreras at this year's trade deadline. His value won't be higher in any transaction cycle moving forward. Count your losses, trade Contreras, and start getting realistic about 2027.

The Red Sox should commit fully to selling (which does not exclude Willson Contreras)

There's been some talk out there about Boston taking on a hybrid, buy/sell approach to the deadline. But this narrative just feeds right back into the notion that the Red Sox are confused about what they want to do, and how they'd like to proceed into the future ... a confusion that delights Yankees observers.

The Yankees, meanwhile, are 100% aware of who they are, where they are going, and what weaknesses they must address at the deadline (bullpen/catcher). Boston and New York are two wildly different ball clubs at the moment. That'll remain the case until the Red Sox establish some clarity about their direction.

Add us as a preferred source on Google

Follow