Yankees have now-or-never chance to heal Red Sox wounds after Alex Bregman decision

For over two decades, the Boston Red Sox have certifiably owned the New York Yankees. The curse-breaking 2004 comeback was both the best and worst thing to happen to any fanbase (arguably) in the history of sports. The Yankees will never truly recover from it unless they replicate the impossible in a once-in-a-lifetime scenario with the roles are flipped.

What they can do, however, is work to further heal those wounds, which still feel pretty raw 22 years later. Some might say the Bombers' playoff victory over the Sox in the 2025 Wild Card round helped — and it did, it was a good start — but it's still a mere footnote compared to the pain Boston has inflicted on the Yanks since 2004.

The Sox have four championships over the span compared to one for the Yankees. They dispatched the Yankees in the 2004, 2018 and 2021 playoffs, and directly robbed New York of championship chances in 2004 and 2018 (let's not kid ourselves and call the 2021 Yankees anything other than an ALDS overachiever).

And all in between, there have been very distinct moments where the Red Sox possessed the "edge" over the Yankees throughout the regular season and with front office decision making. The Jacoby Ellsbury signing. The Gerrit Cole-Rafael Devers one-sided rivalry. Devers' home run off Aroldis Chapman that birthed Joez McFly's viral reaction. Alex Cora telling the Yankees to "suck on it" during the 2018 World Series parade. The Alex Verdugo trade. The Garrett Whitlock Rule 5 Draft. Rob Refsnyder discovering himself in a Sox uniform. Chapman's defection to Boston. Many, many walk-off losses at Fenway and meltdowns on the national stage.

The Yankees' front office has seemingly possessed no interest in going above and beyond to take back control in the rivalry, but now they have one of their best chances since that fateful October in 2004. On Saturday night, Alex Bregman spurned the Red Sox in free agency and chose the Chicago Cubs on a five-year, $175 million contract. Boston fans are up in arms. Craig Breslow and the Sox front office have killed morale once again, this time creating conflict with the face of their franchise in Rafael Devers and then trading him months after signing Bregman. Fans then held out hope that Bregman was the preferred future of the team and that re-signing him was as set in stone as can possibly be.

But it turns out the Sox weren't aggressive enough and Bregman wasn't enthralled with Boston enough. Also, more importantly, Scott Boras just showed Boston fans how the Yankees similarly felt with Juan Soto's departure. You thought there was a connection, didn't you? You didn't think it would come down to every last penny. But it did. It sure did. And this is what happens when you're unwilling to take risks. Yankees fans know the game well.

Cashman's never had a better chance to further dull the Red Sox's edge over the Yanks. New York just beat Boston in the playoffs. The Sox have lost their third superstar player in the last six years and will see another uncomfortable roster overhaul. Boston fans are reaching levels of frustration with their franchise that Yankees fans know well for the past 15 years. That means now is the time for the Yankees be irresponsible in improving their fortunes. Playing it safe is no longer applicable.

Go make 2-3 impact moves right now. We don't care what they are. Overpay for somebody. Throw in an extra top-five or top-10 prospect to get a blockbuster deal done. Shed the current roster of excess salary and any imperfect fits. Add a luxury surplus (another starter? expensive bench piece?). Whatever it is, it'll further back the Sox into a corner as their options dwindle to the point where they will be stuck praying all of their young talent takes the necessary leaps (and we know how unfavorable those odds are).

The Yankees will more than likely never fully stitch up the gaping gash that is 2004. Fans understand that. But chipping away at the Sox Superiority narrative will naturally fade the discourse out more and more. Any recapturing of the upper hand does that, but it's a matter of landing repeated blows rather than infrequent ones.

Cashman can complete the 1-2 punch with a late, aggressive offseason. He can deliver the hook during the regular season, an uppercut during the 2026 playoffs, and then the haymaker when it's curtains on next year (or the next five years). Giving Aaron Judge one World Series ring while the Red Sox plunge into uncertainty as a result of self-inflicted wounds would generate headlines Yankees fans haven't seen in quite some time, and it'll lessen the shine on the Red Sox's relatively dominant run from 2004-2021.