Red Sox could make Yankees regret a trade deadline mistake in hilarious fashion

The New York Yankees were active at the trade deadline, pulling off several deals in an effort to try and win the World Series. They've already seen their moves pay off with Jazz Chisholm Jr. getting off to an unbelievable start at the dish and Mark Leiter Jr. getting some big outs out of the bullpen, but Brian Cashman wanted to do more.

It was reported that the Yankees were very interested in Jack Flaherty but wound up backing out of a preliminary trade agreement due to concerns with Flaherty's medicals. Flaherty had missed a start with a lower back issue at the beginning of July, and the Yankees ultimately let Flaherty go to the Los Angeles Dodgers.

How Flaherty will do for the Dodgers remains to be seen, but if he continues to dominate on the mound, passing on the right-hander could be something that the Yankees regret, especially if they fall short in October.

Not only could the Yankees potentially regret passing on Flaherty now, but the Boston Red Sox could find a way to make the Yankees feel worse about themselves in a hilarious fashion.

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Red Sox could make Yankees regret passing on Jack Flaherty by signing him in the offseason

The Red Sox won't have Flaherty pitching for them down the stretch, but what about 2025? Flaherty will hit free agency this offseason, and the Red Sox certainly feel like a team that could look to sign him.

Of course, this would require the Red Sox actually spending like they're the Red Sox as Flaherty will search for a fairly sizable free agency contract, but assuming they're willing to spend on someone, Flaherty would be a good fit.

The rotation has been an unlikely strength for much of the 2024 campaign, but could easily have a new look next season. Nick Pivetta and James Paxton are both set to hit free agency at the end of the year. What the Red Sox can get from injured starters like Lucas Giolito and Garrett Whitlock is uncertain.

Those questions and potential departures mean that the only starters Boston has locked in are Tanner Houck, Kutter Crawford, and Brayan Bello. Adding a frontline arm like Flaherty could make the rotation extremely formidable, and there's no reason why the Red Sox can't pay him other than not wanting to.

If the Red Sox were to sign Flaherty and succeed with him, that'd be something Yankees fans cannot stand after their team was oh so close to acquiring him.