The Cubs’ offseason is already taking shape around one big truth: the pitching staff is going to look different, and probably a lot different, by the time 2027 opens.
One move that points to how Chicago is managing the puzzle came with Javier Assad. According to Jordan Bastian of MLB.com, the Cubs declined Assad’s $3.3 million team option for the 2027 season.
That doesn’t send him out the door, though. Assad remains under team control through arbitration and is projected to be back on the 40-man roster next season.
The decision is really about dollars. The Cubs can keep Assad for less through arbitration than the amount attached to the option, so this is a cost-saving move more than a goodbye. And with so many pitching decisions ahead, every bit of flexibility matters.
Assad’s value to Chicago is easy to see. He posted a 3.63 ERA in 28 games, including 11 starts, and handled whatever role the Cubs asked him to fill.
He hasn’t had the kind of breakout that changes a roster overnight, but he’s been dependable. If Chicago lands a front-line starter, Assad could fit as a back-end rotation arm.
If the Cubs spread their money around and add multiple starters, he also makes sense as bullpen depth.
That broader pitching plan is where the offseason gets really interesting. Ken Rosenthal said on Foul Territory, “I’m not sure the internal options are sufficient," Rosenthal said regarding Chicago's starting pitching options.
"So, yes, they will be active in the market. I think they will sign or acquire two starting pitchers.
One good thing in their favor is that the market is fairly deep, not in great starters, but starters.”
That lines up with the shape of the Cubs’ rotation right now. Shota Imanaga, Kevin Gausman, Clay Holmes, and David Peterson have all hit free agency.
Matthew Boyd turned down his team option, and Jed Hoyer declined Colin Rea’s option as well. The result is a rotation with plenty of openings and plenty of pressure attached to every move.
Rosenthal also made clear he doesn’t see Chicago going all-in on Tarik Skubal with a franchise-record deal, even though the left-hander was linked to the Cubs again earlier this week. The bigger takeaway is that the Cubs appear set to be aggressive, but not necessarily reckless.
And “acquired” was the key word in Rosenthal’s comments. Free agency is the obvious route, especially with a market that offers plenty of starters.
But the trade market can get busy too, and Chicago has shown it’s willing to make pitching deals over the last year-plus. Seattle could be a team to watch in that mix, especially now that it has a former front office face as its manager.
There’s also another roster decision hanging out there in the background. The Cubs outrighted Tyler Austin to Triple-A Iowa this week, leaving his future unresolved. Austin didn’t play in a Cubs game this season after right knee surgery, though the expectation had been that he would compete for real playing time after agreeing to return to the Majors in December.
Austin’s path has been unusual. He was once a notable Yankees prospect, then spent time with the Twins, Giants, and Brewers before heading overseas to play for the Yokohama DeNA BayStars in Nippon Professional Baseball. From 2020 to 2025, he put together a strong run there, hitting 85 home runs and driving in 236 runs while slashing .293/.569/.377 over six seasons.
At 35, there was never a guarantee that success would carry over in the same way at the MLB level. Still, the Cubs took a shot on the depth piece, and now the question is whether they keep him around and see if he can win a bench role in 2027 or move on after the experiment didn’t really get off the ground.
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