Cubs 2026 Offseason Guide on Free Agents, Trade Targets, More Roster Shakeups After Wild Card Loss

The Chicago Cubs had the highest-scoring offense in baseball in 2026 and were also the league's best defensive team by almost every measure, but that wasn't enough to keep them out of an early playoff exit.

The offense was silenced in Game 1 when Padres ace Michael King carried a no-hitter into the seventh inning, and they fell behind early in Game 2 and couldn't claw back in another quiet night from their bats against Nick Pivetta and the San Diego bullpen.

The biggest immediate question will be whether they push to re-sign one or both of Seiya Suzuki and Ian Happ, but the more pressing need will be to upgrade a pitching staff that was the team's clear weakness throughout the 2026 season.

Rebuilding the bullpen, upgrading the rotation and retooling the outfield are all part of the offseason to-do list, and we've addressed all of that and more in the Cubs' offseason guide.

Free-Agent Hitters

Matt Dirksen/Getty Images

Seiya Suzuki

OF Seiya Suzuki
OF Ian Happ
OF Michael Conforto
OF Tyrone Taylor
1B Tyler Austin

Pete Crow-Armstrong will return to anchor the Cubs outfield from center field, but who will flank him in right and left field is still up in the air.

Seiya Suzuki, Ian Happ, Michael Conforto, and Tyrone Taylor accounted for 295 of the 324 starts at the corner outfield spots, with most of the remaining playing time going to Matt Shaw in his super-utility role, so there aren't many viable in-house replacement options.

Suzuki (131 OPS+, 26 HR, 5.1 WAR) would be extremely difficult to replace in the middle of the lineup, while Happ (103 OPS+, 24 HR, 2.9 WAR) is the team's longest-tenured player and a veteran leader.

The club will likely try to re-sign one of them, but both might be a stretch. A reunion with Taylor, given how well he played in a platoon role against left-handed pitching, is also worth considering.

C Carson Kelly ($7.5 million mutual option)

A middling season from Miguel Amaya and the trade of Moisés Ballesteros leave the Cubs without an obvious replacement behind the plate if Kelly walks after starting 94 games behind the dish in 2026.

The 32-year-old has been a good fit for the Cubs, and while he'll likely decline his end of the mutual option, a quick re-up on a new multi-year deal would make sense for both sides.

Free-Agent Pitchers

Matt Dirksen/Getty Images

Shota Imanaga

SP Shota Imanaga
SP Kevin Gausman
SP David Peterson
RP Aaron Civale

Shota Imanaga was the Cubs' best starter this season, finishing 11-10 with a 3.77 ERA, 1.10 WHIP and 174 strikeouts in 174.1 innings. He remained homer-prone, serving up 35 long balls, but finished on a high note with a 2.25 ERA over five September starts.

Kevin Gausman was a deadline rental, while David Peterson proved to be a great scrapheap pickup, posting a 3.70 ERA in 80.1 innings over 15 starts after the Mets cut him loose.

Veteran Aaron Civale posted a 1.72 ERA over 36.2 innings in 18 relief appearances, recording a pair of saves at the height of the club's bullpen uncertainty. He might prefer a chance to start elsewhere.

SP Matthew Boyd ($15 million mutual option)
SP Clay Holmes ($12 million player option)
RP Hunter Harvey ($8 million mutual option)
SP/RP Colin Rea ($7.5 million club option)
RP Caleb Thielbar ($6 million mutual option)
RP Jacob Webb ($2.5 million club option)

Matthew Boyd and Clay Holmes are safe bets to test free agency, while Hunter Harvey will be a no-brainer to have his option declined and Caleb Thielbar will also likely be cut loose.

Colin Rea (34 G, 19 GS, 4.34 ERA, 137.0 IP) was a valuable swingman, finishing second on the club in innings pitched, and $7.5 million is a reasonable price tag for what he provides.

The easy decision here is to exercise Jacob Webb's reasonable club option, as he recorded a team-high nine saves while posting a 3.36 ERA and 9.8 K/9 in 68 appearances.

Biggest Needs

Matt Dirksen/Getty Images

Justin Steele

Starting Pitching: The Cubs will essentially be rebuilding their rotation from the ground up, assuming Shota Imanaga, Matthew Boyd, Kevin Gausman and Clay Holmes all hit the open market. A healthy Justin Steele should be ready to return to the starting staff, while Edward Cabrera will be given every chance to reclaim his spot in the rotation, but this is a complete teardown-and-rebuild situation.

Relief Pitching: A healthy Daniel Palencia, deadline pickup Ryan Zeferjahn, breakout lefty Ryan Rolison and veteran Jacob Webb give the Cubs some pieces to build around in the bullpen, but they need multiple established veterans to fill in the gaps around them.

Outfielder: Unless they simply re-up with Seiya Suzuki and Ian Happ, which seems unlikely given their expected cost and the team's other needs, the outfield will look new in 2027. Former top prospect Kevin Alcantara could get an extended look this spring, and Matt Shaw could theoretically settle in as an everyday outfielder, but at least one notable outside addition is likely.

Free-Agent Targets

Julio Aguilar/Getty Images

Freddy Peralta

The Cubs should at least be in the Tarik Skubal conversation given their major-market status and clear need for a bona fide staff ace, but this is more than a one-piece-away situation.

Freddy Peralta and Trevor Rogers are the other frontline-caliber arms on the market this winter, while a reunion with Shota Imanaga, Clay Holmes or Kevin Gausman is a possibility. The next tier down will also be in play, with Tyler Mahle, Casey Mize, Nick Martinez, Foster Griffin, Jack Flaherty and Kris Bubic among the names to watch.

On the reliever side of things, Adrian Morejón, Alex Vesia and Bryan Abreu represent proven setup options with premium stuff, while more affordable options like Brock Burke, JoJo Romero and Jason Adam would also provide a boost. As for proven closers, David Bednar and Raisel Iglesias will be free agents, but a healthy Daniel Palencia is likely the ninth-inning guy.

To address the mass exodus in the outfield, expect a push to re-sign Seiya Suzuki or Ian Happ, and perhaps Tyrone Taylor or Michael Conforto if they are amenable to a part-time role.

Taylor Ward, Ramon Laureano and Adolis García are potential buy-low targets, but the trade market might be preferred to breaking the bank on top names like Randy Arozarena or Trent Grisham.

Trade Targets

Steph Chambers/Getty Images

Logan Gilbert

SP Logan Gilbert, Seattle Mariners

With a 3.73 ERA, 1.09 WHIP and 205 strikeouts in 186 innings, Gilbert would comfortably be the No. 2 starter on the market this offseason behind Tarik Skubal if he were a free agent.

Instead, he has one year of club control remaining, and after making just over $10 million in 2026, he will be less of a payroll drain than several second-tier free-agent options. The prospect price would be steep, but he would be an impact addition to plug their biggest roster hole.

SP Joe Ryan, Minnesota Twins

Ryan is in the same free-agent class as Gilbert and was an All-Star for the second straight year in 2026, logging a 3.79 ERA, 1.16 WHIP, and 159 strikeouts in 144.2 innings. The Twins were hesitant to move him last winter, but if they finally lean into a rebuild, he's their top trade chip.

OF Steven Kwan, Cleveland Guardians

Ian Happ has won four straight NL Gold Glove awards in left field. What better way to replace him than with the guy who has won the AL Gold Glove at the same position every year over that same four-year stretch? The Cubs have enough thump to offset Kwan's lack of extra-base impact, and an elite defensive team would arguably get even better while adding a table-setting bat.

Projected 2027 Opening Day Roster

Matt Dirksen/Getty Images

Starting Lineup
C Carson Kelly
1B Michael Busch
2B Nico Hoerner
3B Alex Bregman
SS Dansby Swanson
LF Matt Shaw
CF Pete Crow-Armstrong
RF Seiya Suzuki
DH Owen Ayers (R)

Bench
C Miguel Amaya
1B/OF B.J. Murray
IF James Triantos
OF Kevin Alcantara

A reunion with Seiya Suzuki and a new multi-year deal for Carson Kelly would keep the Cubs' offensive core intact, and Matt Shaw deserves regular playing time in left field after logging a 102 OPS+ over 202 plate appearances in a utility role. They can scour the bargain bin in free agency to fill out the bench, but have plenty of MLB-ready options down on the farm.

Starting Rotation
RHP Logan Gilbert
LHP Justin Steele
RHP Ben Brown
RHP Nick Martinez
LHP Kris Bubic

Bullpen
RHP Javier Assad
RHP Colin Rea
RHP Jacob Webb
LHP Brock Burke
RHP Jason Adam
LHP Ryan Rolison
RHP Ryan Zeferjahn
RHP Daniel Palencia

A blockbuster deal to acquire Logan Gilbert would give the Cubs enough financial flexibility to target a few mid-level arms like Nick Martinez and a healthy Kris Bubic, while Javier Assad and Colin Rea would provide rotation depth. Breaking the bank on a top-tier reliever might not be in the cards, but Brock Burke and Jason Adam can handle high-leverage work.