The Cubs were in the mix for Michael King-until they weren’t. Over the past week, it became increasingly clear that Chicago had faded from the race for the free-agent right-hander, with stronger interest coming from teams like the Yankees, Orioles, Red Sox, and Mets. But in a bit of a curveball, King ended up re-signing with the San Diego Padres on a three-year, $75 million deal that includes opt-outs after both the first and second seasons.
That structure? It’s likely what pushed the Cubs out of contention.
While the money wasn’t necessarily out of Chicago’s range, the flexibility built into King’s deal was something the Cubs have historically shied away from-particularly first-year opt-outs. That’s not just speculation; it’s precedent.
Last offseason, the Cubs made a run at Alex Bregman, but their offer reportedly didn’t include an early opt-out. Bregman eventually signed a similarly creative three-year deal with Boston and, true to form, exercised his opt-out after just one season.
So when King turned down the Padres’ qualifying offer last month, any team other than San Diego would’ve had to give up draft-pick compensation and international bonus pool money to sign him. That’s a steep price before even getting into contract structure.
The Padres, by virtue of being his former team, didn’t face those penalties-and they used that leverage to offer King a deal that gave him both security and flexibility. For King, it’s essentially a supersized version of the qualifying offer with a safety net for 2027 if things don’t go as planned in the short term.
For the Cubs, that kind of deal likely never made it to the table.
And now, with King officially off the board, the Cubs’ search for starting pitching gets a little more urgent. The free-agent market isn’t deep, and based on what’s been reported, the team’s focus seems to be narrowing to two names: Tatsuya Imai and Zac Gallen.
Imai, the 27-year-old right-hander from Japan, has been generating buzz since his posting. His window to sign closes on January 2, and he represents one of the few remaining high-upside arms still available. If the Cubs are going to make a splash this winter-outside of a potential Bregman deal-Imai may be their best shot.
It’s worth noting that Scott Boras represents both Imai and Gallen, which adds another layer to the timeline. Boras is known for playing the long game, and odds are he’ll wait for Imai’s situation to resolve before fully turning his attention to Gallen, the former Diamondbacks ace.
So where does that leave the Cubs? Still in the market, still looking for rotation help, and still trying to thread the needle between financial flexibility and roster impact. Missing out on King stings, but the offseason is far from over-and the next few weeks could be telling in how aggressive Chicago is willing to get.