Red Sox Poised to Splash $110 Million on 2 Top Pitching Acquisitions This Offseason
As the 2024 MLB season draws to a close, the Boston Red Sox enter the offseason with clear priorities. After a rollercoaster year, one thing is undeniable: they need to bolster their roster in key areas to get back into playoff contention. The Red Sox need a right-handed power bat—preferably one that can do damage at Fenway Park’s notoriously short right-field porch. They also need to rework their bullpen, with veterans Chris Martin and Kenley Jansen set to hit free agency. But most of all, the Red Sox need starting pitching—and, if we’re being honest, they could use two new faces in the rotation.
While the Red Sox’s front office isn’t known for splashing big money on long-term pitching deals, it’s clear they have to make moves. And as MLB insider Jim Bowden recently predicted in The Athletic, the Red Sox could opt for quantity over quality in their pitching acquisitions. Let’s take a closer look at how this might shake out for Boston.
Targeting the Mid-Rotation: Jack Flaherty and Yusei Kikuchi?
Bowden’s offseason prediction for the Red Sox’s pitching plans is certainly intriguing. According to his latest piece, he sees the Sox signing two mid-rotation arms with upside: Jack Flaherty and Yusei Kikuchi.
Jack Flaherty: A High-Upside Risk
At 29, Flaherty is one of the more promising arms in free agency, though his career has been a bit of a rollercoaster. Coming off his best season since 2019, Flaherty finished 2024 with a 13-7 record, a 2.95 ERA, and 133 strikeouts in 106.1 innings. He had a solid year split between the Detroit Tigers and Los Angeles Dodgers, with L.A. relying on him in high-leverage moments during their playoff run, even though he wasn’t particularly dominant in the postseason. Still, Flaherty’s regular-season performance—especially his ability to handle pressure—has earned him a place in the Sox’s plans.
Flaherty has always had the stuff to be a top-of-the-rotation arm, but injuries and inconsistency have prevented him from reaching that potential consistently. The Red Sox would be betting on a rebound season from the right-hander, hoping he can find the consistency he’s lacked in past years. A three-year, $68 million deal would give him the opportunity to prove he can be a reliable middle-of-the-rotation fixture.
Yusei Kikuchi: A Rejuvenated Veteran
Then there’s Yusei Kikuchi, a 33-year-old lefty who has had a somewhat up-and-down career since coming over from Japan. Kikuchi has been a solid contributor for the Toronto Blue Jays but truly found his stride after being traded to the Houston Astros at the 2024 trade deadline. While he posted a 9-10 record and a 4.05 ERA for the season overall, his second-half performance with Houston was stellar. Over his final 10 starts, Kikuchi went 5-1 with a 2.70 ERA and a 0.933 WHI, showing that he could still be an effective starter when he’s on.
A three-year, $42 million deal would be a low-risk move for Boston, and Kikuchi could provide solid depth in the middle of the rotation, especially with his ability to eat innings. If the Red Sox take a chance on him, they would be betting on his late-season surge continuing into 2025.
The Pitching Depth: Is it Enough?
Bringing in Flaherty and Kikuchi would give the Red Sox a potentially deep rotation. With Lucas Giolito expected to return after missing 2024 due to elbow surgery, and the team’s decision to extend a qualifying offer to Nick Pivetta, the Sox could have as many as seven starting pitchers in the fold heading into next season.
– Jack Flaherty
– Yusei Kikuchi
– Lucas Giolito
– Nick Pivetta(if he accepts the offer)
– Tanner Houck (who took big strides in 2024)
– Bryan Bello (a young arm with potential)
– Kutter Crawford (a steady presence)
This rotation is full of arms with varying degrees of upside and risk. Tanner Houck could be poised for a breakout in 2025, though he might not be quite ready for an ace role yet. Meanwhile, Garrett Whitlock should return from elbow surgery and could be a big boost, although he’ll likely return to the bullpen, where he’s been most effective in his career.
Red Sox Chief Baseball Officer Craig Breslow made it clear that pitching is the team’s primary focus this offseason. The decision to extend the qualifying offer to Pivetta is a reflection of this commitment. Breslow told reporters, “We’ve been pretty outspoken about our need for pitching…we’ll see how things play out from here.” That’s a clear indication that, while the offense may get some tweaks, the starting rotation will be the team’s primary area of improvement.
The Bigger Picture: Is This Enough?
While adding two mid-rotation arms is a step in the right direction, it’s unlikely to be enough for the Red Sox to truly contend in 2025, especially in the AL East. If they’re serious about competing for a playoff spot, they’ll need to add more power to the lineup and, at the very least, shore up the bullpen. Given the volatility of both Kikuchi and Flaherty, as well as the uncertainty around Pivetta’s performance, Boston will still need some luck and growth from younger pitchers like Bello and Houck.
But, given their track record of avoiding long-term, high-priced pitching contracts, this approach—a mix of low-risk, high-reward signings—feels more in line with the Red Sox’s current philosophy. With the right mix of veteran stability and emerging talent, this might just be the formula that gets the Red Sox back into contention.
Conclusion
The Red Sox are clearly focused on improving their pitching staff this offseason. Bringing in Jack Flaherty and Yusei Kikuchi could give them a deeper and more reliable rotation, while also preserving financial flexibility for other moves. However, with the lineup still needing a legitimate power threat and the bullpen in flux, the Red Sox will have plenty of work to do if they’re to challenge for the playoffs in 2025. The next few months will be crucial in shaping the team’s future, and how they balance their pitching depth with offensive improvements will likely determine whether they can make the leap from also-ran to contender.
