Aug 10, 2025; San Diego, California, USA; San Diego Padres starting pitcher Dylan Cease (84) leaves the game during the sixth inning against the Boston Red Sox at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images
San Diego, California – It’s shaping up to be another winter of hard decisions in San Diego, and this time the Padres’ pitching staff looks like the unit most likely to take the hit. With Dylan Cease and Michael King both headed for free agency and both projected to draw significant interest across the league, the Padres may be preparing to watch two of their most important arms walk.
San Diego’s payroll is already top-heavy, tied down by long-term deals for the franchise cornerstones they’ve chosen to build around. That makes it difficult — maybe impossible — for the front office to keep pace in a bidding war for starting pitching this winter.
Around the league, executives believe both Cease and King could cash in. But at least early on, King looks like the pitcher generating the most realistic buzz. Jim Bowden of The Athletic projected King to land a four-to-five-year deal worth around $75 million — a contract that, for many clubs, might still feel like a bargain for a pitcher who’s only just beginning to tap into his ceiling as a starter.
And according to The Athletic’s Andy McCullough, that demand may take King straight out of San Diego. In his latest offseason predictions, McCullough has King signing with the Chicago Cubs, calling him an ideal mix of upside and affordability for a team trying to rebuild its rotation without spending Gerrit Cole money.
“The Cubs may well get out-bid for the services of King by a team more willing to pay top dollar for a talented pitcher who has not yet proved he can handle the rigor of a full season as a starter,” McCullough wrote. “But King has an elevated ceiling… and likely won’t require a long-term deal.”
For Chicago, the fit is obvious. The Cubs are bracing to lose key pieces in free agency and need to replace star-level production without ballooning their payroll. King offers frontline potential at a lower cost than the top arms on the market, which frees up money for the Cubs to pursue help in the outfield and elsewhere. It’s a roster strategy that makes sense for them — and a scenario that would leave the Padres without one of their most dynamic late-season performers.
The bigger question for Padres fans is what comes next. Losing Cease and King would force San Diego to lean heavily on internal options and lower-cost rotation targets — a tough path when the rest of the NL West continues to load up. The Padres still have the top-end talent to compete, but pitching depth remains their biggest offseason challenge.
A.J. Preller has pulled off surprises before, and the Padres have rebuilt rotations on the fly in the past. But unless the market breaks San Diego’s way, this winter looks like the one where the Friars will need to get creative again — and hope their young arms are ready for bigger roles in 2026.
For now, Padres fans should brace for an offseason defined by tough departures and a search for value. The names leaving might be big, but the pressure on the front office to keep the Padres competitive will be even bigger.
