Predicting 2 Ideal Landing Spots For Dylan Cease In Free Agency

Dylan Cease will be one of the most popular names on the market

Oct 1, 2025; Chicago, Illinois, USA; San Diego Padres starting pitcher Dylan Cease (84) delivers a pitch against the Chicago Cubs in the first inning during game two of the Wildcard round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images | Matt Marton-Imagn Images

Dylan Cease is one of the top free agent starting pitchers entering the 2025-26 offseason. The action has yet to begin, but will soon, and Cease should be highly sought-after.

However, he struggled in 2025, going 8-12 with a 4.55 ERA in 32 starts and pitching 168 innings with the San Diego Padres. He may be forced to settle for a shorter-term contract this winter as a result of those struggles.

Regardless of the kind of deal he receives, he’ll still be one of the most popular names on the market. These two teams could be perfect fits for him this offseason.

San Francisco Giants

Sep 28, 2025; San Francisco, California, USA; San Francisco Giants starting pitcher Logan Webb (62) walks to the dugout against the Colorado Rockies in the first inning at Oracle Park. Mandatory Credit: Eakin Howard-Imagn Images | Eakin Howard-Imagn Images

The Giants have already grabbed some headlines this offseason thanks to the surprising hire of former Tennessee baseball head coach Tony Vitello as their new manager. But they have shown a willingness to spend money in recent winters.

Last offseason, they signed Willy Adames to a seven-year, $182 million contract. Cease may get a shorter deal, but he still won’t come cheap. But the Giants need to replace Justin Verlander and could use a top-level starter to go with Logan Webb.

This could help at least get San Francisco back into the conversation for a Wild Card spot in 2026. They need pitching help after having acquired Rafael Devers from the Boston Red Sox, and Cease could make them a more complete team.

Boston Red Sox

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox starting pitcher Garrett Crochet (35) pitches against the New York Yankees during the third inning of game one of the Wildcard round of the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

The Red Sox are another team that could use a little help in their rotation. Having somebody to go next to Garrett Crochet could give them a boost as they try to bounce back from their Wild Card Series loss.

The main focus for Boston will be keeping Alex Bregman, but their pitching issues cannot be overlooked. A move to sign Cease could put them on the same level with the New York Yankees and Toronto Blue Jays and give them a chance to compete for the top spot in the American League East.

Cease would bring swing-and-miss capability to a rotation that needs another top arm. Boston could have a chance to go deeper into the postseason in 2026. 

He is the type of arm that Boston needs to improve for next season and beyond, and it will certainly be interesting to see how Boston goes

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