The World Series is almost over, so it’s that time of year when MLB insiders start releasing their top free-agent lists. This week, Jim Bowden’s top-40 free-agent list over on The Athletic is gaining traction, and he has five Chicago Cubs free agents in his rankings heading into the 2026-27 offseason.
As a reminder, up to 17 players on the Cubs’ 2026 MLB roster could be eligible for free agency this winter. Roster turnover will be heavy heading into next season, and the Cubs will need to be active to replace a lot of talent. Most, if not all, of the five most popular Cubs free agents on Bowden’s list will likely sign elsewhere in free agency. We’ll list them from the highest to lowest ranking on Bowden’s top-40 free agent list.
Seiya Suzuki (No. 6)
Seiya Suzuki should be near the top of the Cubs’ offseason wishlist, as the right fielder has been one of the team’s most consistent offensive performers since arriving in 2022. The right-handed hitter posted a 134 wRC+ in 2026, with a .270/.368/.473 slash line and 26 home runs.
Suzuki will likely depart in the offseason because his contract will price the Cubs out. At least that’s the early sentiment among team insiders, as the Cubs are expected to focus most of their resources on pitching this offseason.
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Best Team Fits | Contract Prediction (according to Jim Bowden):
Toronto Blue Jays, Philadelphia Phillies
Contract: 5 years, $120 million
Clay Holmes (No. 10)
The starting rotation will be the Cubs’ No. 1 priority heading into 2027, and after trading away top prospect Jefferson Rojas, you have to imagine Jed Hoyer wants Clay Holmes for more than just a couple of months.
The veteran right-handed pitcher has the ideal pitching profile to work in front of the Cubs’ elite defense. He was injured in 2026, but that came from a fluke incident in which Holmes suffered a broken bone in his leg after being hit by a line drive. Holmes is a two-time All-Star as a reliever, and in 2025, the righty excelled in his first full season as a starter, posting a 3.53 ERA over 165.2 innings.
Best Team Fits | Contract Prediction (according to Jim Bowden):
San Francisco Giants, Chicago White Sox
Contract: 2 years, $44 million
Ian Happ (No. 19)
The most polarizing player for the Cubs in recent memory is, without question, Ian Happ. The 10-year pro will now be a free agent for the first time in his career, and the Cubs haven’t exactly extended an olive branch to the left fielder.
Happ put up a down 2026 season, with a slash line of .218/.326/.412, 24 home runs, and a 107 wRC+. The switch-hitter was also largely forced into a platoon role after the trade deadline, with the arrival of Tyrone Taylor. You shouldn’t rule out a reunion on a short-term deal, but the Cubs won’t give Happ a raise in 2027, which Bowden’s contract prediction suggests.
Best Team Fits | Contract Prediction (according to Jim Bowden):
Chicago Cubs, Cincinnati Reds
Contract: 2 years, $45 million
Shōta Imanaga (No. 21)
The overall numbers were fairly decent in 2026 for left-hander Shōta Imanaga: a 3.77 ERA and 24.6 K%, and he also had another healthy year, making 32 starts and logging 174.1 innings, but this marriage needs to end.
For the second straight postseason, the Cubs avoided using Imanaga in an elimination game; he gave up the second-most home runs as a starter; and at a projected salary of $20+ million per year, the Cubs need a higher ceiling to upgrade their rotation.
Best Team Fits | Contract Prediction (according to Jim Bowden):
Chicago Cubs, Houston Astros, San Francisco Giants
Contract: 3 years, $69 million
Kevin Gausman (No. 25)
Like Imanaga, the Cubs simply need to aim higher this offseason in their starting pitcher targets. Kevin Gausman was fine after the Cubs acquired him from the Toronto Blue Jays at the trade deadline, but fine isn’t going to cut it moving forward.
Plus, it seems like Gausman is either thinking about calling it quits or is leaning toward returning to the Blue Jays to end his career, so it may be out of the Cubs’ control regardless of their level of interest.
Best Team Fits | Contract Prediction (according to Jim Bowden):
Chicago White Sox
Contract: 1 year, $22 million
