The Cubs are staring at a busy offseason, and the list of players eligible for free agency after 2026 is long enough to keep the front office occupied for a while. Some decisions are straightforward.
Others are more complicated. A few feel like the kind of calls that will tell you exactly where Chicago’s priorities really are for 2027 and beyond.
Start with the easy money: the Cubs should exercise all three of their club options.
Javier Assad’s $3.3 million option looks like a no-brainer. The 29-year-old did what he always seems to do for this pitching staff - show up, give the Cubs useful innings, and keep the train on the tracks.
He made 11 starts, pitched in 28 games overall, and posted a 3.63 ERA across 94.1 innings in the regular season. Assad isn’t going to wow anybody with pure stuff, but he’s been steady, and his career 3.47 ERA in 106 MLB games backs that up.
He can start, work as a swingman, or handle relief. However the Cubs want to use him, he gets outs.
Colin Rea’s situation costs more, but it still lands in the same bucket. His club option is $7.5 million with a $1 million buyout, which effectively makes it a $6.5 million decision.
Rea has started the third-most games for the Cubs over the last two seasons, even if that wasn’t exactly by design. He was pushed into a starting role in each of the last two years and held up well enough to matter.
Over two seasons in Chicago, he owns a 4.13 ERA in nearly 300 innings. That’s the kind of dependable work the Cubs can use.
Then there’s Jacob Webb, whose $2.5 million option might make some fans groan, but the broader picture still points toward a return. His final five weeks were rough, no question.
Still, he also put together a run of 24.2 scoreless innings over two months, and his career numbers are strong enough to matter: a 3.07 ERA in 315 MLB games. At that price, the Cubs can justify keeping him in the bullpen - as long as they make sure he’s not the guy finishing games in September again.
The lone player option belongs to Clay Holmes, and he’s expected to decline it. The $12 million player option is set to go unused, which sends him into free agency.
Holmes came to the Cubs after the Mets signed him to a three-year, $38 million deal before 2025, a move that turned heads because New York planned to convert him from reliever to starter. That conversion worked.
He became an All-Star again in 2025 and brought that starter profile with him to Chicago.
His time with the Cubs was uneven. He looked dominant in August, then collapsed in September so badly that the Cubs kept him out of the Wild Card Series and held him back for a possible Game 3 against the San Diego Padres.
Even so, the appeal is obvious. Holmes had a 60.7% ground ball rate in 2026 and a 62.3% mark for his career, which fits nicely with the Cubs’ elite infield defense.
There’s also the simple optics of it: Chicago traded away top prospect infielder Jefferson Rojas to get him, and it would look awfully strange to let Holmes walk after only a few months. Expect the Cubs to be in the mix hard, and expect them to want him back.
The corner-outfield situation is messier. Tyrone Taylor and Michael Conforto are both unrestricted free agents, and the Cubs probably should bring back one of them, but not both. With Seiya Suzuki and Ian Happ also free agents and their futures described as uncertain at best, there’s not exactly a clean path here.
If the Cubs are looking at value, Taylor makes the most sense. He’s a short-side platoon bat who fit in well after arriving from the Mets at the deadline with Holmes.
He can handle either corner and even give Pete Crow-Armstrong a break in center field, which he did a few times late in the year. Taylor’s resume doesn’t stack up to Conforto’s, but that also means his market should be lighter.
If Chicago is going to spend most of its energy on pitching, a more modest deal for a fourth outfielder feels a lot more realistic than paying Conforto to be a regular.
Suzuki is the name the Cubs should be fighting to keep. The problem, according to early reports from team insiders, is that the front office doesn’t sound eager to enter a bidding war for him.
That’s a tough stance to take on a player who has delivered consistent power for four years, averaging 25 home runs per season since 2023. His OPS has stayed above .800 throughout his five-year MLB career, including an .840+ OPS in three of the last four seasons.
The defense criticism has always felt a little exaggerated, too. In 2026, Suzuki tied Victor Mesa Jr. of the Tampa Bay Rays for the highest Fielding Run Value among MLB right fielders, according to Baseball Savant.
He’s the kind of bat that’s hard to replace, and the Cubs may end up losing him anyway. His slumps have been frustrating, but his overall production has earned him a longer runway.
If he leaves, it won’t be because the case for keeping him was weak. It’ll be because Chicago’s pitching needs apparently won out.
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