Every Cubs free agent next offseason and who is most likely to stay or leave

The Chicago Cubs stunned fans after their Opening Day loss by signing second baseman Nico Hoerner to a six-year contract extension. The move, which seemingly everyone has been begging the team to complete for months, secures Hoerner's long-term future with the team and makes next year's offseason much more manageable for the front office.

Even with Hoerner staying put, the Cubs still have a lot of prominent players hitting free agency after 2026. They can't extend everybody, nor should they, so this season will be very important for those guys hitting the market. I'm going to go over all of them and predict who will stay and leave Chicago.

Outfielders: Ian Happ, Seiya Suzuki, Dylan Carlson, Michael Conforto

Dylan Carlson and Michael Conforto signed minor league contracts with the Cubs and played their way onto the Opening Day roster. Although both are bench guys, Conforto and Carslon will have more opportunities to play until Seiya Suzuki returns from his knee injury. It's difficult to say whether either man will be back since they aren't likely to be in positions to significantly impact the team.

Conforto is more likely to return, especially if he returns to his 25+ home run status as he did in his initial years with the New York Mets. But that will depend on how much playing time he gets, and if Suzuki and Happ see significant time on the injured list.

I wouldn't be surprised if the Cubs tried to extend Happ next. In a lot of ways, this is Happ's team. He is the longest tenured Cub, a four-time Gold Glove winner in left field, and a consistent on-base machine. All of this, combined with the fact that next year's free-agent class is scarce as far as outfielders go, makes me think Happ will be back with the team. Albeit for the right price, since Happ is far from an elite talent. But I suspect the Cubs would like to keep him around with the current group.

Suzuki will be more difficult to keep, especially because his stock is already high. He's coming off a career year where he smacked 32 home runs and drove in 103 runs. The Cubs have already spent the most money they have in the last decade this offseason, and Suzuki won't be cheap.

Matt Shaw started in right field on Opening Day, and the Cubs could see him as a long-term solution in their outfield mix. If Shaw proves to be a capable defender there, I'd bet Suzuki will not be in Chicago past 2026.

Starting Pitchers: Shota Imanaga, Jameson Taillon, Matthew Boyd

I can confidently say that the Cubs' starting rotation will look very different in 2027, and I don't think Shota Imanaga, Jameson Taillon, or Matthew Boyd will be back. All three men are on the wrong side of 30 and have all shown signs of their production deteriorating.

Taillon will be 35 next year, missed significant time due to injury in 2025, and struggled with giving up home runs when he was healthy. Imanaga was ineffective for much of the second half of 2025, to the point where the Cubs were not willing to pick up his three-year club option in the offseason.

Boyd is technically not a free agent since he has a $15 million club option for 2027. A club option that I have a hard time seeing the Cubs pick up. While Boyd was fantastic with a 3.21 ERA last year, he slowed down in the postseason, and it's unrealistic to expect him to produce like he did as he approaches his age-36 season next year.

The Cubs will have Justin Steele, Cade Horton, and Edward Cabrera still under contract, with affordable club options for Javier Assad ($3.3 million) and Colin Rea ($7.5 million). And the Cubs' top pitching prospect, Jaxon Wiggins, will have a full season in the Iowa Cubs' rotation this year if he can stay healthy, which will hopefully prime him for a big-league rotation spot in the future.

If the Cubs let Boyd, Taillon, and Imanaga walk, they will also have $57 million coming off their payroll, some of which can be used in an intriguing starting pitching market. I don't expect the Cubs to land a big fish like Tarik Skubal, who is poised to land a mega deal after back-to-back Cy Young Awards. But names like Freddy Peralta, Zac Gallen, and Brandon Woodruff could be realistic options.

I hate to be so analytical about this because Boyd, Taillon, and Imanaga have been integral players for the Cubs in recent years, and it will be hard to see them leave. They all helped this team make the postseason last year and gave Cubs fans great memories. But age becomes a factor for every player in MLB at some point, and the Chicago front office is clearly committed to making the Cubs a persistent contender, especially after extending Hoerner and Pete Crow-Armstrong. And to do that, the starting rotation needs to get younger at some point.

Relief Pitchers: Hoby Milner, Caleb Thielbar, Hunter Harvey

Relief pitchers' futures are notoriously hard to predict since they are the most volatile players in baseball. There's no guarantee these guys will even be on the team in June. It's entirely dependent on how they perform.

Milner is on a one-year deal worth $3.75 million. Thielbar and Harvey have mutual options for next year, but I included them because mutual options are rarely exercised. Hopefully, all three guys pitch well this year because the Cubs have been very good at retooling their bullpen on the fly under Jed Hoyer. The only guy I am fairly comfortable predicting won't be back in 2027 is Thielbar, who will be 40 next year.