MLB Insider Doesn't Believe Cubs Will Land Prized Free Agent

The Chicago Cubs have an important offseason ahead. 

This Cubs team could look very different between now and the start of the 2027 season. They have a long list of free agents, including Ian Happ, Seiya Suzuki, Shota Imanaga, Tyrone Taylor, Kevin Gausman, and likely Clay Holmes. 

The biggest question mark surrounding this team heading into the next year is what this rotation will look like. With Imanaga, Gausman, Holmes, and Matthew Boyd all hitting free agency, the Cubs will need some rotation help. 

As of now, the only starters the Cubs have under contract for next season are Edward Cabrera, Justin Steele, Javier Assad, Cade Horton, Braxton Garrett, and Ben Brown. Horton will miss most of the 2027 campaign while he recovers from Tommy John surgery, and there are concerns about the other five pitchers. 

Cabrera had a career-worst year in his first year in Chicago. Steele has missed most of the last two seasons. Assad doesn’t miss many bats. Garrett might not be ready for a spot in the rotation, and it’s unclear whether Brown’s neck issue will still be acting up. 

That will force the Cubs to be aggressive to land multiple starting pitchers this offseason. The good news is that a handful of quality pitchers are available for the front office to target in free agency. 

Gausman, Holmes, Michael King, Casey Mize, Nick Martinez, and Robbie Ray could all be available for the Cubs to pick up in free agency. One of the best pitchers in baseball in Tarik Skubal also happens to be available on the open market. 

Skubal is easily the best free-agent pitcher available this coming offseason. The southpaw is a two-time Cy Young winner and is coming off another elite season in 2026 in which he finished with a 2.72 ERA and 186 strikeouts across 158 ⅔ innings. 

So, what are the chances that the Cubs could pick up a pitcher of that caliber in free agency? MLB insider Jon Morosi doesn’t give the North Siders much of a chance to outbid top market teams to sign Skubal. 

“There’s going to have to address this rotation in a pretty convincing way,” Morosi said on 104.3 The Score. “You need a little bit more swing-and-miss. You need a probably true No. 1. They’re going to have to look at it and say, ‘Are we ready to go toe-to-toe with the New York Mets and maybe the Dodgers in the bidding for Skubal?’ I tend to think they will fall short.”

Skubal is obviously going to command a lot of money on the open market, and it would be quite a surprise to see the Cubs throw the bag at the 29-year-old left-hander. It’s hard to imagine them outbidding teams like the Dodgers, Mets, Yankees, and even the Blue Jays for the multi-time All-Star. 

Skubal is going to want over $350 million. The Cubs likely won’t be giving out that type of money in free agency.