Dylan Cease enters this offseason as one of the most intriguing arms on the MLB free-agent market, a pitcher who will command attention this winter even after an up-and-down stretch in recent years. With elite strikeout stuff, big-game flashes, and the durability contenders covet, Cease is positioned to draw interest from clubs looking for both upside and stability in the middle of their rotation.
MLB Free Agency: Where Will Dylan Cease End Up This Offseason?
Here are three possible destinations for Cease this offseason:
Boston Red Sox
The Red Sox have a clear number one option in Garrett Crochet, but the direction that they are taking with the rest of their rotation is unclear. They will certainly be hitting the free agent market this offseason as some of last year’s arms are no longer under contract, and Dylan Cease could be a real option as a high-ceiling starter to anchor the top of their rotation.
If Boston is willing to make that kind of investment, Cease could slot in just behind (or alongside) Crochet to form a fearsome top of rotation. Cease’s 2025 surface numbers weren’t spotless, as his 4.55 ERA and 1.33 WHIP suggest volatility. But that risk may be worth it for Boston, because his underlying profile indicates a strong bounce-back candidate.
The only FA pitcher I'd want the sox to sign would be Dylan Cease. If you can't get him, go trade for one. pic.twitter.com/Sl9Mk1r9hx
— Payton Tolle Enthusiast (@TolleEnthusiast) November 21, 2025
Chicago Cubs
The Cubs exceeded most expectations in 2025, and will need to do some re-tooling of the roster if they want to continue contending next season and beyond. One of the better pieces of their pitching rotation will likely be gone with Shota Imanaga hitting free agency himself, and they aren’t exactly top-heavy. Matthew Boyd, who is slated to be the team’s #1 pitcher, is 34 years old and had a career ERA of 4.85 before his first MLB All-Star selection in 2025.
Cease would be a viable option, and he could even compete for one of the top rotation spots.
There is also a familiarity component. Cease was originally part of the Cubs’ system, drafted by Chicago and later traded away, so a return would carry both competitive and emotional value. Pitching in Wrigley could suit him exceptionally well, as his agent Scott Boras has even said that Cease “is dominant” when he’s on the mound in Chicago, suggesting he sees a strong fit.
Longest Active Streaks of 32+ Start MLB Seasons:
Dylan Cease, 5 years
Logan Webb, 4 years
Yusei Kikuchi, 3 years
6 other guys, 2 years pic.twitter.com/FEiZ3hopes— Codify (@CodifyBaseball) November 21, 2025
San Francisco Giants
The Giants head into the offseason with plenty of uncertainty surrounding their starting staff. Logan Webb is firmly entrenched as the ace, and Robbie Ray remains in place for another year, but beyond that, there’s a mix of developing arms and unproven depth. That reality makes it likely San Francisco will turn to the open market to stabilize the group.
Among the top starting pitching options available, Cease could be a match for what the Giants need. He’d slot comfortably behind Webb as a dependable No. 2, bring valuable innings to a rotation that needs them, and benefit from the pitcher-friendly environment at Oracle Park.
For a club aiming to elevate itself from respectable to legitimately competitive, securing Valdez would represent a major step toward solidifying a critical part of their roster.
