Red Sox Need Starting Pitching, So What Might It Cost In Free Agency?

The Red Sox’s starting pitching simply wasn’t good enough in 2023.

So, it’s fair to assume Boston will make every effort to improve its rotation this offseason, knowing it could determine the team’s success in 2024.

The good news for the Red Sox? There are several impactful starters available in Major League Baseball free agency.

The bad news? They won’t come cheap.

Then again, such is life when shopping on the open market, where teams must pay up for premium talent. The challenge lies in figuring out who to target, how aggressive to be and where to draw the line in negotiations.

The Red Sox have deep pockets relative to many other teams across the league. But they’re not going to spend recklessly. Nor should they. It’s all about finding value, then pushing in your chips when warranted.

Chris Sale remains under contract through 2024, with a club option for 2025. So, let’s assume he maintains a spot in Boston’s rotation. Brayan Bello is a lock, as well, based on the upside he showed last season.

Beyond that, the calculus becomes murky. Kutter Crawford exceeded expectations in 2023 and deserves strong consideration for a spot. Garrett Whitlock and Tanner Houck could factor into the equation, as well, though the jury still is out on whether they’re better suited for the bullpen. Same goes for Nick Pivetta, a talented but unpredictable veteran whose Red Sox tenure has been all over the map from a performance standpoint.

The Red Sox probably would prefer to add at least two starters this winter, with the trade market being another avenue Boston can explore. Maybe that pursuit leads them down a path where they open up the checkbook for a top-flight arm. They’re seemingly well positioned financially for such an expenditure after staying under the luxury tax threshold in 2023.

But just how much are we talking?

Obviously, it’s difficult to pinpoint an exact dollar amount. There are so many factors involved, and one major development could have a significant domino effect on the landscape. Say Team A overpays for Player B. That might raise the price of Player C for Team D. Get ready to haggle.

Fortunately, The Athletic’s Tim Britton and Jim Bowden both offered contract projections for top free agents last week. Britton’s projections took into account historical comps, factoring in each free agent’s recent performance relative to the performance of past free agents before signing their deals. Bowden is a former MLB executive with ample front-office experience.

Here’s what they’re projecting for several notable starting pitchers.

Yoshinobu Yamamoto, RHP (25 years old)
Britton: Seven years, $203 million (plus $32.3 million posting fee)
Bowden: Seven years, $211 million

Aaron Nola, RHP (31 years old)
Britton: Six years, $180 million
Bowden: Five years, $125 million

Blake Snell, LHP (31 years old)
Britton: Five years, $135 million
Bowden: Five years, $122 million

Jordan Montgomery, LHP (31 years old)
Britton: Five years, $105 million
Bowden: Five years, $127 million

Eduardo Rodriguez, LHP (31 years old)
Britton: Five years, $80 million
Bowden: Five years, $90 million

Sonny Gray, RHP (34 years old)
Britton: Three years, $72 million
Bowden: Three years, $64 million

Lucas Giolito, RHP (29 years old)
Britton: Four years, $70 million
Bowden: Two years, $24 million (with an opt out after the first year)

Jack Flaherty, RHP (28 years old)
Britton: Three years, $45 million
Bowden: One year, $10 million with incentives

*all ages reflect the player’s age on June 30 of the 2024 season

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Of course, this isn’t the full list of free agent starters. Other available hurlers include Clayton Kershaw, Michael Wacha, Andrew Heaney, Tyler Mahle, Frankie Montas, Mike Clevinger, Lance Lynn, Kenta Maeda, Hyun Jin Ryu and Shōta Imanaga.

The above estimations at least offer a snapshot, though, of what the Red Sox might be getting into should they direct their attention toward free agency.

And if you’re wondering about Shohei Ohtani, well, join the club. Has there ever been a more fascinating free agent given his star power and excellence as a two-way force? He’s truly a unicorn.

Unfortunately, Ohtani likely won’t pitch in 2024 after undergoing Tommy John surgery. But Britton projected he’ll land a 12-year, $520 million contract, whereas Bowden predicted a 10-year, $477 million agreement “with incentives and escalators that take the deal to more than half a billion dollars.”