The Cubs have room to make noise this offseason, and the biggest swing might come on the trade market. With Jed Hoyer working with more money than usual, Chicago has a chance to attack several needs at once and set itself up for 2027. The most obvious one sits right at the top of the rotation.
That’s where Drew Rasmussen enters the picture.
Chicago’s season was a strange one in a lot of ways. Pete Crow-Armstrong led a historic team, the Cubs finished with the best defense in baseball, and the roster featured multiple Gold Glove winners and an MVP.
But none of that stopped the postseason from turning sour. The offense never caught fire at the right time, the club finished the regular season 5-5 over its final 10 games, and then San Diego swept the Cubs out of the Wild Card Series.
The pitching staff had its own problems, too. At times, the rotation and the rest of the staff went cold, and the starting pitching remains the area that has to be addressed first. That’s been the message all along: the Cubs need depth, and they need it badly.
Free agency gives them one path. Promoting from the farm system gives them another.
But if Chicago wants a true difference-maker, a trade may be the cleanest route. Rasmussen fits the bill as an elite arm with the kind of experience teams covet when the games get bigger.
He’s exactly the sort of pitcher the Cubs have been missing since the 2016 World Series run. Chicago has tried to build from within, but the results haven’t been there.
Outside of Cade Horton, who is dealing with an injury, the organization hasn’t developed much in the way of reliable arms. And with free agency offering no guarantees on top names like Tarik Skubal and Michael King, a trade for Rasmussen starts to make a lot of sense.
According to baseball insider Jeff Passan, Rasmussen is expected to be one of the top trade candidates this offseason. That lines up with Tampa Bay’s situation after the Rays exercised his $20 million option, pushing them above their payroll without any other moves. The Rays can shuffle other pieces if they want, but Rasmussen figures to draw real attention and a real return.
The buzz around him is already out there. Joe Ryan or Drew Rasmussen in a Cubs uniform? 👀 @sahadevsharma suggests Chicago “check in on a lot of guys,” identifying Seattle, Miami, Tampa Bay and Minnesota as potential trade partners. pic.twitter.com/QtlXhAsDW7
For the Cubs, the question is whether they’re willing to pay the price. They should be.
Rasmussen would cost plenty, but that’s what it takes to land a starter who can anchor a staff. In 2026, he went 16-5 with a 2.67 ERA and piled up a career-high 174 strikeouts.
He also comes with back-to-back All-Star appearances.
Jed Hoyer has been more willing to get aggressive in the trade market over the last two seasons, and this is the kind of move that would fit that approach. It wouldn’t fix everything, but it would give Chicago a much-needed No. 1 starter and a real shot at reshaping the rotation. Rasmussen is the kind of arm that can change the look of a Cubs staff in a hurry.
In Other News...
Cubs May Be Running Out Of Time On Two Former Top Prospects
The Cubs have a few moving parts already lined up for 2027, with internal names such as Matt Shaw, Pedro Ramirez, Justin Steele and Edward Cabrera expected to take on larger roles as openings develop in the rotation and outfield. But while the organization has some clarity on the next wave, it also has two former top prospects still sitting on the 40-man roster in Kevin Alcantara and Jordan Wicks, and both are at a point where the clock is starting to matter.
Alcantara and Wicks have not gotten enough consistent playing time to settle their cases, and performance concerns have only added to the uncertainty around where they fit long term. With the Cubs also staring at a potential roster crunch before the anticipated MLB lockout in December 2026, the front office may be forced to sort out those decisions sooner rather than later, even if the picture on both players is still incomplete. [Read more 🡒]
Cubs May Already Have A 2027 Outfield Decision Coming Into Focus
The Cubs defensive identity showed up in a big way this season, with the club taking home the National League Gold Glove Award and Pete Crow-Armstrong among the individual honorees. Even with that success fresh in view, the front office is already looking farther ahead, because the outfield picture for 2027 could look very different than the one fans are used to seeing now.
Crow-Armstrong appears likely to be part of that next wave, but Ian Happ and Seiya Suzuki may be headed toward free agency by then, which puts some pressure on the organization to plan early. Two internal names to watch are Josiah Hartshorn and James Triantos, both of whom offer the kind of versatility teams value when roster construction gets tight, with Hartshorns defensive flexibility and recent jump to Double-A standing out and Triantos bringing minor league production plus the ability to move around the diamond. [Read more 🡒]
Cubs Outfield Reality Is Starting To Crush The Dream Options
The Cubs offseason priorities are coming into focus, and the outfield market is starting to look a lot less glamorous than some fans might have hoped. Chicago is expected to spend most of its energy on pitching in free agency, while the idea of swinging a blockbuster deal for a superstar outfielder has quickly drifted into the background.
Bryce Harper and Ronald Acua Jr. are the kind of names that can ignite a winter, but the reality around both makes those dreams feel remote. Harpers contract is a major obstacle, and Acuas trade status is uncertain enough to make a deal unlikely, which leaves the Cubs pointing toward shorter commitments for veteran hitters and more affordable outfield help on the open market. [Read more 🡒]