Red Sox must overcome fallout from former MVP's trade to land big FA fish

Boston's "negative player perception" is hampering their quest to improve their rotation.

Boston Red Sox End Of Season Press Conference
Boston Red Sox End Of Season Press Conference | Billie Weiss/Boston Red Sox/GettyImages

Money isn't everything. The Boston Red Sox — winners of four World Series this century — are finding that out the hard way this free agent cycle.

Boston used to be a prime free agent destination. But so far this offseason, all has been quiet on the northeastern front. Two of the Red Sox reported top targets — Yusei Kikuchi and Blake Snell — went and stayed west instead of inking deals with the once-cursed franchise.

The Great Bambino's sway over Boston's postseason success has long been lifted, but another significant trade may have had a larger impact on them than initially imagined. According to ESPN's Buster Olney, the Red Sox decision to not pay Mookie Betts back in 2020 has harmed their pursuit of pitching this year.

Boston, who went 81-81 in 2024, had six members of their regular lineup post an OPS+ above 110 last season. They had just one starting pitcher (Tanner Houck) record an ERA+ greater than 105.

Why do the Red Sox need to upgrade their rotation?

On the surface, Boston's starting pitchers appear to be fine. The Red Sox finished with the seventh-best starting pitcher ERA (3.81) in 2024. And while Houck was the only regular starter with an ERA+ above 105, Boston also didn't have a rotation holder finish with an ERA+ below 95 (100 is league average).

What does this indicate? Well, for starters (pun intended), it means the Red Sox didn't have any rotation member absolutely tank their season. However, it also shows they lacked star power in that department.

The high floor, low ceiling (and low cost) approach doesn't bode well in a division as tough as the AL East. You have to have stars, which is why chief baseball officer Craig Breslow clamored about "raising the ceiling" of his rotation shortly after free agency began.

However, saying you want to open the checkbook and actually doing so are two different things. It's still early, but free agents are clearly wary of Boston. We don't know what contract they offered Kikuchi, but they're certainly closer to contention than the Angels.

Snell spurning them for the Dodgers is another class of conversation. That type of pull is something the Red Sox used to possess. Now, they're relegated to second-tier or lower in free agents' minds because of their Betts debacle. Things won't change until they find a way — whether it's for their lineup or rotation's sake — to make a legitimate splash.

If Breslow's aspirations for Kikuchi and Snell are an indication of the Boston's plans, the names to watch now may be Max Fried and Sean Manaea. Boston has no left-handed starters in their projected rotation, so it makes sense for them to diversify. If the Red Sox lure one of them to town, their perception could change for the better and make Boston a preferred landing spot once again.

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