The Boston Red Sox will commit to actually contending in the AL East one of these years. A disappointing first season post-Chaim Bloom ended with Boston staring up at the first-place New York Yankees, helmed by arguably the two best players in the entire American League. Boston’s aspirations go beyond toppling New York, of course, but it’s never fun in Boston when the Yanks are front-running.

It’s not difficult to poke holes in the Red Sox roster, but the quickest path to winning baseball games in today’s MLB is an elite pitching staff. Boston has a ways to go in that department, especially after Brayan Bello failed to take the leap many expected from him in 2024.

Boston should get immediate reinforcements with the return of Lucas Giolito, who missed all of last season after elbow surgery. But, further additions would push Boston into a different tier. While the Red Sox aren’t always as aggressive as fans would like in free agency, a robust pitching market could play into Boston’s hands. The options are plentiful.

Over at The Athletic, former MLB GM Jim Bowden has an enticing prediction for Boston — a three-year, $68 million contract for Jack Flaherty.

That’s quite the steal for the Red Sox, but unfortunately, Flaherty might hang up the phone before Boston can even put such an offer on the table.

Red Sox-Jack Flaherty link could dissolve after Dodgers World Series victory

Here’s the problem with predicting Jack Flaherty to leave the Los Angeles Dodgers — he’s a Los Angeles kid, born and raised, and he just won it all with the team he grew up rooting for. At the Dodgers’ parade in downtown LA, Flaherty made it clear where he wants to spend the rest of his career.

“I love this city. I never want to leave.”

That’s a bummer for the Red Sox hopefuls. The door isn’t completely shut — we’ve seen countless free agents leave happy marriages for a bigger paycheck — but Flaherty is on the Dodgers, a team that does not historically cheap out on free-agent offers. It was not a seamless postseason run for Flaherty, but he came through when it mattered and delivered for an injury-riddled rotation. He is an instant legend in that town.

It sure sounds like Flaherty would take a hometown discount to ride out the next decade in a Dodgers uniform. He won’t get a decade-long contract, of course, but Flaherty could balk at the concept of returning to the northeast, where his last experience (in Baltimore) wasn’t so hot. The AL East did not treat Flaherty kindly in 2023, and while Boston’s a different team, Flaherty has zero evident motivation to leave his current spot.

Free agent contracts are mutual, of course. The Dodgers need to want Flaherty back, which could get complicated with Shohei Ohtani, Tyler Glasnow, and potentially even Clayton Kershaw healthy and in the mix next season. Moreover, big-ticket free agents like Blake Snell or Corbin Burnes could steal attention away from Flaherty. That is surely what the Red Sox are hoping for — a distraught, impatient Flaherty who isn’t willing to wait on the Dodgers’ more ambitious free-agent pursuits.

Adding Flaherty and Giolito to the mix next season would change how folks talk about the Red Sox. It’s worth noting that Giolito and Flaherty were high school teammates once upon a time. Until the ink is dry on the dotted line, however, Boston fans shouldn’t get their hopes up.