The Cubs have a pitching offseason to navigate, and the board breaks into three very different lanes: the swing-for-the-fences dream, the name that actually makes sense, and the kind of deal that can haunt a front office.
Tarik Skubal sits at the top of the wish list. Even if the Los Angeles Dodgers and New York Mets are expected to be the favorites for him, the Cubs shouldn’t be treated like a punchline here.
They have the financial room to jump into the conversation, and this is exactly the kind of move that would test whether Chicago is willing to use spending as a real edge over the Milwaukee Brewers. With over $100 million coming off their books this offseason and clean books moving forward, the Cubs can fit Skubal’s contract without worrying about the implications under revamped payroll rules.
The only question is whether they act like a team that belongs in that race.
Sonny Gray is the more grounded possibility. He didn’t pile up eye-popping strikeout numbers with the Boston Red Sox in 2026, but he checked plenty of other boxes.
Gray was a finalist for the most outstanding pitcher award for the American League league, which tells you how strong his season was overall. He’s also been tied to the Cubs for years, and this could finally be the moment Jed Hoyer gets his guy.
His 2.70 ERA and 46% ground-ball rate last season point to a pitcher who still has plenty to offer.
Then there’s the trap door: Casey Mize. On paper, he looks like the kind of arm a team convinces itself it can fix, but the price tag would be steep.
Spotrac has his next contract valued at over $100 million for six years, and no club should be eager to go there. Mize has shown flashes, but durability has been an issue, and the buyer’s remorse is hard to miss.
He posted a 7.46 ERA with the Padres over his last 10 starts, and his fastball velocity was trending down at the same time.
In Other News...
Cubs Wasted An Elite Defensive Season Fans Still Cant Ignore
The Cubs can take some comfort from the fact that their defense was recognized as one of the best in baseball after the 2026 season, with Sports Info Solutions naming them its Fielding Bible Team of the Year. Pete Crow-Armstrong also earned the outlets Player of the Year honor on defense, another reminder of how much value Chicago got from a unit that regularly saved runs and changed innings even when the rest of the roster had other issues.
What makes the award sting a little is how little it ultimately changed the clubs fate. Chicagos pitching staff never matched the standard set behind it, and the season ended quickly in the Wild Card Round against the Padres. Crow-Armstrongs individual recognition only adds to the odd contrast, since he was honored as the games top defensive player even while another center fielder, Ceddanne Rafaela, took the nod at the position. [Read more 🡒]
Cubs May Have A Risky October Pitching Decision To Watch
Brandon Woodruff is back on the Brewers World Series roster after recovering from shoulder inflammation, a reminder of both the upside and the uncertainty that have followed him lately. For the Cubs, who are expected to monitor the pitching market closely, his name carries obvious appeal: when Woodruff is healthy, he has looked like the kind of arm that can change a rotation conversation in a hurry.
The question, of course, is how much confidence a team can place in a pitcher whose recent seasons have been interrupted by shoulder issues and limited playing time. Woodruff is expected to hit free agency next month, and Chicagos reported interest figures to come with the same caution as the upside, leaving the Cubs to weigh whether the talent is worth the risk if they decide to make a run at him. [Read more 🡒]
Cubs Lefty Bullpen Plan May Hinge On One Tough Decision
Ryan Rolison gave the Cubs exactly the kind of left-handed bullpen work they were hoping for in 2026, handling a heavy workload across 60 appearances while finishing with a 3.14 ERA and missing bats at a better-than-average rate. With his rights secured through the 2029 season, the organization has some long-term stability there, and all signs point to Rolison sliding back into that relief role again in 2027 as Chicago keeps sorting out the left side of its bullpen.
The question is whether the Cubs believe that version of Rolison is the one they can count on going forward, or whether the underlying numbers suggest some caution before they pencil him in too confidently. That uncertainty is why a name like Dodgers free agent Alex Vesia makes sense in the conversation, since adding another proven lefty would give Chicago more insurance if Rolisons metrics point toward regression rather than repeat production. [Read more 🡒]