The Chicago Cubs have many players heading into free agency after the 2026 season, but not all of them will leave. A handful of players will have their club options picked up, while a few others could certainly be re-signed. But who should return for 2027 and beyond, and who should never come back? Let’s go over the list, starting with the trio of pitchers most likely to return based on their club options.
Club Options: Cubs Should Pick Up All 3
Javier Assad ($3.3 million club option)
The 29-year-old pitcher had another great year being the perfect fill-in guy for the Cubs’ pitching staff. Assad made 11 starts, appeared in 28 total games, and finished the regular season with a 3.63 ERA in 94.1 innings. He’s not flashy, doesn’t have the best stuff in the league, but he’s been dependable, now recording a 3.47 ERA in 106 career MLB games.
Assad can start, serve as a swingman out of the bullpen, or pitch in a more traditional relief role. No matter what, he gets outs. The $3.3 million club option will be an easy decision for the Cubs.
🔥 Subscribe to the Untold Chicago YouTube channel to hear Chicago legends tell stories you’ve never seen in headlines — real moments, real experiences, straight from the athletes themselves.
Colin Rea ($7.5 million club option, $1 million buyout)
Did you know Rea has started the third-most games for the Cubs in the past two years? It definitely wasn’t by choice, but the veteran righty was asked to step into a starting role in each of the last two seasons, and like Assad, he was an underrated arm who helped a lot. In two years with the Cubs, Rea has posted a 4.13 ERA in nearly 300 innings.
This one will cost the Cubs a bit more, but given the club option worth $7.5 million, including a $1 million buyout, it’s really a $6.5 million decision to retain a steady pitcher.
Jacob Webb ($2.5 million club option)
I can hear Cubs fans screaming to stay the hell away from Webb, but as horrific as the reliever was during the final five weeks of the regular season, you also can’t ignore his overall season and previous work in the big leagues.
Webb had a streak of 24.2 scoreless innings over two months, and while he might not have been that amazing, you also can’t assume he’ll keep being as bad as he was down the stretch. The right-handed reliever has a career 3.07 ERA in 315 MLB games. At $2.5 million, Webb should be back in the bullpen next season, and obviously the Cubs should be making several more moves so that he’s not the one responsible for closing out games in September.
Now, let’s move on to the only guy who has a player option, who will decline it and become a free agent. He sucked at the end, but he’s also the perfect pitcher to be in the middle of the Cubs starting rotation.
Clay Holmes ($12 million Player Option)
The New York Mets signed Clay Holmes to a three-year, $38 million contract prior to the 2025 season. It was a decent chunk of change, but it also caught the baseball industry a bit off guard, as the Mets signed the pitcher with the intention of turning him into a starting pitcher.
Before the 2025 season, Holmes had four MLB starts, all during his rookie year with the Pittsburgh Pirates in 2018. Since then, Holmes was your traditional one-inning reliever, and from 2021-24, he was the go-to man in the New York Yankees bullpen. The righty saved 74 games in his last three seasons with the Yankees, including a 2022 All-Star nod.
But Holmes flawlessly returned to a starter role with the Mets and became an All-Star again in 2025.
He looked dominant in August with the Cubs, then fell apart in September. He was so bad that the Cubs stayed away from him, holding him back for a potential Game 3 against the San Diego Padres in the Wild Card Series. Yet, you look at his jaw-dropping ability to produce ground balls- a 60.7% ground ball rate in 2026 and a 62.3% ground ball rate in his career- and Holmes’ pitching profile is ideal with the elite infield defense that the Cubs feature.
You also have to think the Cubs don’t want to look really stupid by losing Holmes after having him for only a few months, after trading away their top prospect at the time, infielder Jefferson Rojas. So, while Holmes will opt out to test free agency, you should expect the Cubs to be heavily interested in re-signing Holmes, and they should bring him back.
Tyrone Taylor/Michael Conforto (Unrestricted Free Agents)
Take your pick here. The Cubs should bring back one of these two, but not both. We’ll see which direction the organization takes at corner outfield, since Seiya Suzuki and Ian Happ are also free agents this offseason and their futures with the Cubs seem uncertain at best.
I tend to lean toward Tyrone Taylor because of the price. He’s a short-side platoon bat who did a phenomenal job after the Cubs acquired him from the Mets, along with Holmes, at the trade deadline. Taylor can play either corner spot, and he can also give Pete Crow-Armstrong a breather in center field, as he did a handful of times late in the year.
Taylor’s track record isn’t as strong as Michael Conforto’s, so his market won’t be as high. Since the Cubs are already expected to divert most of their resources to the pitching staff, a modest deal for a fourth outfielder like Taylor seems more in their wheelhouse than paying Conforto as a starter.
Seiya Suzuki (Unrestricted Free Agent)
The Cubs should absolutely try to re-sign Seiya Suzuki this offseason, but it pains me to say early reports from team insiders indicate the front office isn’t interested in a bidding war for the right fielder.
Suzuki has been a consistent power bat for the Cubs for the past four years, averaging 25 home runs per season since 2023. His OPS has remained above .800 in his five-year MLB career, including an .840+ OPS in three of the last four years. His defense has always been maligned, but that was a bit unfair because a handful of lousy plays skewed that perception. In reality, Suzuki has been a solid defender in right field, and in 2026 he tied Victor Mesa Jr. of the Tampa Bay Rays for the highest Fielding Run Value mark in MLB among right fielders, according to Baseball Savant.
It is going to be a damn shame when Suzuki eventually signs elsewhere this upcoming winter because his production won’t be easy to replace. His slumps were downright annoying, but Suzuki has done more than enough to earn a longer look from the Cubs, whose pitching situation will apparently keep them from competing for his services in free agency.
