The Cubs may be shopping for help in the outfield this winter, but the idea of a blockbuster swing for Bryce Harper or Ronald Acuña Jr. got shut down fast.
On the latest episode of North Side Territory, The Athletic’s Patrick Mooney and Sahadev Sharma made it clear they do not expect Chicago to land either superstar, despite the loose speculation that has floated around as the Cubs look toward free agency. The dream scenario has been easy for fans to imagine, especially with talk that the Phillies could move Harper and the Braves could consider Acuña. The reality, according to the insiders, is much less dramatic.
Bryce Harper? Ronald Acuña Jr.? Don’t get your hopes up, Cubs fans... ☹️ @sahadevsharma doesn’t see Chicago making a blockbuster outfield addition, expecting the Cubs to pursue shorter deals with veteran hitters instead. pic.twitter.com/bsxSBUk8aa
- North Side Territory (@NSideTerritory) November 6, 2026
Harper, in particular, looks like a nonstarter for Chicago. The Cubs once had a future mapped out that included him after the 2018 season, but that path changed when Tom Ricketts effectively limited the spending of Theo Epstein’s front office. That left Chicago without the flexibility to chase Harper when he reached free agency.
Now, Harper is on the back end of a 13-year, $330 million contract and under team control through the 2031 season. The source material makes the case bluntly: there just isn’t a realistic scenario in which the Cubs would take on that money. If anything, the only reason the Phillies would consider moving him would be to unload the contract, and Chicago is not the kind of club that would step in as the escape hatch.
Acuña is a different financial conversation, but the reporting still doesn’t point toward a deal. He is making $17 million in 2017 and has a $17 million club option for 2028, which is far more manageable than Harper’s number. Even so, there has been no credible indication that Atlanta is actually trying to move him.
That leaves the Cubs where they were always more likely to land: on the smaller end of the market. With Seiya Suzuki potentially departing and a hole opening in the lineup, Chicago is expected to look for veteran bats on shorter contracts rather than chase a headline-grabbing trade. Taylor Ward and Trent Grisham are the kinds of names fans should be watching, not Harper or Acuña.
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 Offseason May Come Down To One Aggressive Pitching Decision
The Cubs offseason pitching plans are starting to sound less like a shopping list and more like a fork in the road. After another year of searching for more depth and stability on the mound, Chicago is weighing whether to simply add arms around the edges or make a bolder move for a starter who can change the shape of the rotation.
Drew Rasmussen has emerged as the kind of name that fits that bigger swing, especially with the Rays payroll situation making him a logical trade candidate. For the Cubs, the appeal is obvious: a chance to chase a true No. 1 type rather than patching over their recent pitching issues one piece at a time, even if nothing has been finalized yet. [Read more 🡒]