The Blue Jays lived up to their promise to stay aggressive this winter when they
signed starting pitcher Dylan Cease on a seven-year, $210 million deal (with deferrals). By handing out one of the largest contracts so far this offseason, Toronto is setting the tone for the free-agent market for starting pitching and is effectively extending its contention window.
There’s no doubt that Toronto’s front office is risking its future by signing a longer contract with a pitcher like Cease, as any long-term contract comes with considerable risk (especially for pitchers) Even if it ages poorly down the line, this deal would have been worth every penny, mainly because of the upcoming starting pitching free-agent market in the winter of 2026.
Once the 2026 season is over, the Blue Jays will be in a starting rotation reconstruction mode again, with notable potential
departures like José Berríos (opt-out), Shane Bieber, and Kevin Gausman. That would leave the front office to scramble to fill crucial vacancies, and without any key signings from this winter, the team would have been in a much more vulnerable position compared to other contenders.
Below is a
list of potential free agents for the 2026 offseason:
- Tarik Skubal
- Brandon Woodruff
- Kevin Gausman
- Shane Bieber
- Shota Imanaga
- Freddy Peralta
- Chris Sale
- Jack Flaherty
- Trevor Rogers
- Sandy Alcantara (club option / $21 million)
- José Berríos (opt-out / $24 million)
- Matthew Boyd (mutual / $15 million)
- Corbin Burnes (opt-out / $30.8 million)
- Kyle Freeland (conditional player option / $17 million)
- Sonny Gray (club option / $30 million)
- Clay Holmes (conditional player option / $17 million)
- Reynaldo López (club option / $8 million)
- Nick Pivetta (opt-out / $14 million)
- Antonio Senzatela (club option / $14 million)
- Luis Severino (player option / $22 million)
- Jeffrey Springs (club option / $15 million)
- Garrett Whitlock (club option / $8.3 million)
Hypothetically, there will be roughly 34 starting pitchers on the market for next year’s free agency, but there are chances where players and clubs pick up the remaining option. There are also opportunities for trades and extensions as well, which could shrink the starting pitching pool by the time winter of 2026 rolls around.
Objectively speaking, the upcoming starting pitching free agent class doesn’t present many superstars outside of one name that sticks out in Skubal. Aside from Skubal, Corbin Burnes, and Chris Sale, there are more depth starters on this list. That’s not to say that there aren’t many competent pitchers for next winter. Names like Shane Bieber, Jack Flaherty, Shota Imanaga, Freddy Peralta, Trevor Rogers, and Brandon Woodruff should still draw strong interest, so long as they continue to show improvements or consistent performances during the 2026 season.
However, bringing solid starting pitchers in free agency won’t be easy for contenders because of fierce competition and higher price tags. Attempting to fill multiple holes in the starting rotation for the 2026 offseason would be a tall task. From that perspective, the
Blue Jays have proactively addressed this concern by signing Cease to a long-term deal.
Historically, the team relied heavily on free agents to fill out the rotation because it lacked internal pitching depth. Based on this track record, the Blue Jays understood that improving starting pitching would always be necessary every offseason, at least until they can bring up many stronger starters from their farm system. Adding someone like Cease, in that sense, was the team’s effort to rebuild its starting pitching depth gradually.
Even if the Jays lose Berríos, Bieber and Gausman next winter, the Blue Jays would still have Dylan Cease and Trey Yesavage, which gives them a good long-term foundation for the team. Ideally, there will also be an unlikely or expected internal hero stepping up to take a spot in the starting rotation, which would only leave the Blue Jays to bring in two more starting pitchers from the free-agent market in 2026.
In what could be a more intense starting pitching market for next winter, the Blue Jays wouldn’t have to worry about completely creating a new rotation and would focus on diversifying the starting rotation composition by bringing depth starters. This would allow the front office to play at a mid-tier starting pitching market, rather than solely going all in on the top-tier.
While bigger contracts get the most spotlight, under-the-radar signings are the ones that pay off the most, given their contract and time values, overall. Having the luxury to explore sneaky starters–think Matthew Boyd, Reynaldo López, Nick Pivetta and Patrick Sandoval–would help the team spend money elsewhere to solidify the roster, while building a rotation more sustainably.
Bringing a free-agent starter will always cost a fortune and will remain a huge gamble. The Blue Jays took on that risk head-on by bringing Cease now so that they won’t have to take that risk every offseason. There are still too many unknowns in this deal, and next offseason, when betting on a sure thing is virtually impossible. Toronto took a calculated risk; how that will age remains to be seen.
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