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    Tom Carroll
    Nov 28, 2025, 11:00
    Updated at: Nov 28, 2025, 11:00

    How Dylan Cease signing a seven-year deal with the Blue Jays impacts Boston's plans on continuing to improve its starting rotation this offseason.

    With Dylan Cease no longer an option after signing a seven-year, $210 million contract with Toronto on Wednesday, the Red Sox are back to surveying a pitching landscape that’s gotten thinner and more complicated by the week.

    Boston entered the offseason vowing to upgrade its rotation with at least one high-impact arm. And in adding Cardinals righty Sonny Gray via trade on Tuesday, they’ve certainly done that. But as Boston fans and media look up and down the Red Sox rotation, it’s clear that the need for a true No. 2 behind Cy Young runner-up Garrett Crochet is still apparent.

    Cease, at 29 years old, would have fit that role perfectly. His disappearance from the board doesn’t end the club’s search, but it does change the menu.

    The Red Sox will now need to pivot decisively, with free agency and the trade market still offering potential solutions at varying price points.

    Here are the most realistic avenues remaining:

    1. Framber Valdez

    For my money, he’s the most dependable ace still available on the free agent market.

    Valdez is the type of pitcher who instantly reshapes a rotation the moment he puts on the uniform.

    Among the remaining arms on the market, he stands out as the rare free-agent starter who combines top-end production with year-over-year consistency. He’s a heavy ground-ball machine with a deep arsenal, capable of pitching deep into games and neutralizing power hitters - a particularly valuable trait in Fenway Park. And while he got rocked during his lone appearance in Boston in 2025, that was more of the exception for Valdez than the rule.

    For the Red Sox, who haven’t had a dominant volume-eating lefty anchor since Jon Lester, Valdez represents the closest thing to a frontline stabilizer remaining.

    He won’t come cheap. Valdez’s age, resume, and track record of durability will push his market toward the top of the remaining class. Even if you think 32 years old is too old to be handing out big money to, that’s what the market has been dictating over the past five-or-so years. You pay for the short term gain and you eat the long term pain. That’s the game these true contenders are comfortable playing.

    If Boston wants a pitcher who minimizes volatility and provides postseason-caliber reliability, this is the clearest path to replacing the type of upside Cease would’ve brought.

    Aug 3, 2025; Boston, Massachusetts, USA; Houston Astros starting pitcher Framber Valdez (59) pitches during the fourth inning against the Boston Red Sox at Fenway Park. (Bob DeChiara/Imagn Images)

    2. Michael King

    King is a high-upside play with shorter-term appeal.

    His emergence as a full-time starter the last two seasons has turned plenty of heads. And even with injuries limiting him in 2025, he still showed enough swing-and-miss ability and command growth to make him one of the more intriguing free agents available.

    He isn’t the sure-thing workhorse that Valdez is, but he fits the mold of the “value growth” pitcher that all teams are always on the lookout to acquire: athletic delivery, expanding pitch mix, and baseball-nerd statistical trends pointing in the right direction.

    For Boston, King represents a smart medium-range investment.

    He might not require a massive long-term contract given he’s only sporting a two-season sample size as a starter, making him a flexible addition who could slot anywhere from No. 3 to a soft No. 2 depending on how Gray pans out in 2026.

    If the Red Sox want to leave room for additional upgrades - perhaps another starter or bullpen reinforcement - King fits both the budget and the competitive timeline.

    Jun 29, 2024; Boston, Massachusetts, USA; San Diego Padres starting pitcher Michael King (34) pitches during the first inning against the Boston Red Sox at Fenway Park. (Bob DeChiara/Imagn Images)

    3. Aaron Civale

    Make no mistake about it, Civale is not a No. 2. With that said, he is a steady back-end option with innings to offer.

    If the Red Sox go bigger on one move (more on that coming up) and need a second, more affordable rotation piece, Civale becomes a natural match.

    He’s not a strikeout-heavy arm, nor is he going to headline a staff, but Civale’s track record as a dependable, strike-throwing mid-to-back-end starter holds real value for a Boston team that has struggled to keep its rotation intact over a 162-game season. Durability alone would immediately make him a valuable piece for the organization - he’s averaged nearly 128 innings pitched per season over the last four years.

    Civale thrives by mixing pitches, avoiding walks, and working efficiently. He’s the type of pitcher who can take the ball every fifth day and give you five or six quality innings - the kind of stability that frees the bullpen from overload and allows the top of the rotation to do its job.

    For a team balancing long-term planning with a desire to remain competitive right now, Civale is a clean, practical fit.

    Oct 4, 2025; Milwaukee, Wisconsin, USA; Chicago Cubs pitcher Aaron Civale (38) pitches against the Milwaukee Brewers during the sixth inning of game one of the NLDS round for the 2025 MLB playoffs at American Family Field. (Benny Sieu/Imagn Images)

    4. Tarik Skubal

    This is obviously the blockbuster dream scenario, and is what I was talking about when I said “more on that coming up.”

    Even after making a deal for Gray, Boston still has the prospect capital to explore major trades, and Skubal remains the crown jewel.

    Winning his second-consecutive American League Cy Young Award in 2025, Skubal brings elite velocity, command growth, and frontline performance that rivals any ace in baseball. The Tigers aren’t eager to move him - nor should they be - but a monster offer could force a conversation.

    And with Skubal and the team reportedly a staggering $250 million a part on contract talks, it’s clear as day that the 29-year-old is gone after his deal is up.

    It would require a franchise-altering package, the kind Boston hasn’t offered since the Chris Sale trade. But if the Red Sox want a true No. 1 who elevates the ceiling of the entire roster, Skubal is that kind of swing.

    And I will reiterate - it’s going to take WAY more than what former MLB general manager Jim Bowden suggested in The Athletic earlier this month.

    Aug 11, 2023; Boston, Massachusetts, USA; Detroit Tigers starting pitcher Tarik Skubal (29) pitches against the Boston Red Sox during the first inning at Fenway Park. (Eric Canha/Imagn Images)

    5. Hunter Greene

    This would be a high-octane bet on development that I am on the record saying I am all in for.

    If Boston prefers upside without the prohibitive cost of Skubal, Greene is the next-best alternative.

    His fastball routinely hits triple digits, and his slider is already elite; the challenge is honing the command and durability needed to reach his ceiling.

    Cincinnati may be more open to moving pitching for controllable bats, which aligns well with what Boston can offer.

    Greene is riskier than Skubal, but his long-term upside is enormous at age 26. He fits the timeline of a young core that should peak over the next several seasons.

    Jun 1, 2023; Boston, Massachusetts, USA; Cincinnati Reds starting pitcher Hunter Greene (21) throws a pitch against the Boston Red Sox in the first inning at Fenway Park. (David Butler II/Imagn Images)

    So where does Boston - currently seventh in World Series odds at OddsTrader - go from here?

    The Red Sox still have paths to meaningful rotation upgrades, just not the straightforward one Cease would have provided.

    Whether it’s the stability of Valdez, the upside of King, the practicality of Civale, or a blockbuster move for Skubal or Greene, Boston can still reshape its staff outside of the Gray addition.

    But the clock is ticking, the market is tightening, and the urgency to act has only increased.

    The next move will tell us exactly how serious the Red Sox are about contending in 2026.


    Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.