This season didn’t end the way the Chicago Cubs wanted. While they achieved the original goal of returning to the playoffs for a consecutive season — something they haven’t done in close to a decade — they had their doors blown off in the Wild Card Round by the San Diego Padres.
It was a tough pill to swallow for the team with the sixth-highest payroll in MLB. Heading into the offseason, their payroll number falls to eighth. Which means they’ll have extra cash to spend to bolster the roster around MVP candidate Pete Crow-Armstrong and try to make a World Series run in 2027.
But what players could they target this winter? We offer up 12 bold, and also realistic, options in the months ahead, including superstar pitcher Tarik Skubal.
Michael King, SP
12Sep 29, 2026; San Diego, California, USA; San Diego Padres pitcher Michael King (34) reacts after the fifth inning against the Chicago Cubs during game one of the Wildcard round for the 2026 MLB Playoffs at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images
While the Cubs could be in the market for Skubal, a strong Plan B in the second tier of free-agent pitchers this winter is Padres starter Michael King, if he opts out of his deal this offseason. King is a battle-tested starter who has been a borderline All-Star for much of the last six seasons. He handles pressurized situations well — as he showed with seven no-hit innings against the Chicago Cubs in the Wild Card Series — and he would be a viable option as a frontline starter next season.
Randy Arozarena, OF
12Sep 27, 2026; Seattle, Washington, USA; Seattle Mariners left fielder Randy Arozarena (56) hits a two-run doubleduring the sixth inning against the Los Angeles Angels at T-Mobile Park. Mandatory Credit: Stephen Brashear-Imagn Images
After a bit of a down year in 2024, eight-year MLB veteran Randy Arozarena has had a resurgence in his early 30s with a pair of strong seasons the last two years. However, 2026 was his best yet as he posted a .281 average and .865 OPS. With 26 home runs, 79 RBIs, 113 runs scored, and 23 stolen bases.
Chicago could lose two of their three outfielders in free agency this winter. The three-time All-Star would be a strong option to replace the numbers they would lose if Seiya Suzuki signed elsewhere this offseason.
Joe Ryan, SP
12Sep 19, 2026; Anaheim, California, USA; Minnesota Twins pitcher Joe Ryan (41) pitches during the second inning against the Los Angeles Angels at Angel Stadium. Mandatory Credit: Kiyoshi Mio-Imagn Images
While the 2027 season is in limbo and we don’t know if it will come with a new salary cap, it is very likely that Twins pitcher Joe Ryan will not opt into another season in Minnesota and will seek out a multi-year deal in free agency.
Although he finished the season with a 4.60 ERA, Ryan is a two-time All-Star and is in the middle of his prime at 30 years old. He would be a great addition to a team that needs more high-level starters in the rotation if they want to compete with the elites in the National League.
Raisel Iglesias, RP
12Sep 29, 2026; Cumberland, Georgia, USA; Atlanta Braves pitcher Raisel Iglesias (26) pitches against the Philadelphia Phillies in the ninth inning during game one of the Wildcard round for the 2026 MLB Playoffs at Truist Park. Mandatory Credit: Dale Zanine-Imagn Images
If you want to be competitive in MLB, you can never have enough pitching in the bullpen. Especially in the late innings of games. That is why Atlanta Braves closer Raisel Iglesias should be on the Cubs radar in the offseason.
While he turns 37 in January, he had another strong year for the Braves as he posted a 2.55 ERA and 34 saves for the National League East champs. If Chicago really wants to make a World Series run in 2027, they need a proven closer, and Iglesias is one of the better options available in free agency.
Tarik Skubal, SP
12Sep 14, 2026; Cincinnati, Ohio, USA; Los Angeles Dodgers starting pitcher Tarik Skubal (29) pitches against the Cincinnati Reds in the first inning at Great American Ball Park. Mandatory Credit: Katie Stratman-Imagn Images
The two-time Cy Young is the best talent — by far — on the free agent market this winter. And he will be looking for the biggest contract a starting pitcher has ever received. A potential salary cap could change a lot of teams’ plans to pursue Skubal, but if there is one thing the Cubs lack, it is an elite ace pitcher.
But if signing Skubal meant letting players like Suzuki and Happ walk in free agency, it would be a worthwhile swap for a player who is considered the best pitcher in the game. The Cubs would still be good offensively if they lose Happ and Suzuki, but their pitching staff would look far different with Skubal at the top of it.
Jazz Chisholm Jr., INF/OF
12Sep 9, 2026; Bronx, New York, USA; New York Yankees second baseman Jazz Chisholm Jr. (13) looks on during the eighth inning against the Colorado Rockies at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images
Another options as a potential replacement in the outfield for Happ or Suzuki this winter is two-time All-Star Jazz Chisholm Jr. Yes, he is streaky and can be a handful in the locker room. However, despite his flaws, he has a legit power bat and can steal bases (He had a career-best 41 this season).
Chisholm Jr. is still only 28 years old, and because he had a down year in 2026, he might be available at a reasonable price. The goal would be to play him in the outfield, but he is a versatile defender who can also be used at third, short, and second.
Carlos Estevez, RP
12Sep 20, 2025; Kansas City, Missouri, USA; Kansas City Royals pitcher Carlos Estévez (53) on the mound during the ninth inning against the Toronto Blue Jays at Kauffman Stadium. Mandatory Credit: William Purnell-Imagn Images
An intriguing name to watch on the reliever market this winter is two-time All-Star Carlos Estevez. In 2025, he led MLB with 42 saves and had a 2.45 ERA. He was one of the best closers in the game. However, in 2026, a freak shoulder injury forced him to the sidelines all year before he eventually needed season-ending surgery.
If his shoulder is healthy and there is a belief that he can return to the pitcher he was last year, Estevez would be an intriguing offseason target if the cost is reasonable.
Bryce Harper, 1B/DH/OF
12Sep 30, 2026; Cumberland, Georgia, USA; Philadelphia Phillies outfielder Bryce Harper (3) rounds the bases after hitting a solo home run against the Atlanta Braves in the eighth inning during game two of the Wildcard round for the 2026 MLB Playoffs at Truist Park. Mandatory Credit: Brett Davis-Imagn Images
Not all of the options to upgrade the roster will be in free agency. There has been recent speculation that the Philadelphia Phillies will take a hard look at trading two-time MVP Bryce Harper.
Harper would be an obvious option for the outfield, first base, or DH in 2027. While the Cubs don’t necessarily need him, the X-factor he brings on the field, in the locker room, and how he plays in the playoffs are unique talents that make him feel like the missing piece of a World Series team.
Hiromi Itoh, SP
12Mar 14, 2026; Miami, FL, United States; Japan pitcher Hiromi Itoh (14) delivers a pitch against Venezuela in the sixth inning during a quarterfinal game of the 2026 World Baseball Classic at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images
As mentioned above, the Cubs need to upgrade their rotation. That is why six-year Japanese League veteran Hiromi Itoh should be on their radar. The 29-year-old posted a 3.44 ERA in 172.2 innings for the Nippon-Ham Fighters in 2026. He has a seven-pitch arsenal, a fastball that can hit as high as 96 mph, and he used it all to win the Sawamura Award — Japan’s version of the Cy Young Award — a year ago.
Itoh would be a very nice option as the Cubs’ new No. 2 or 3 starter in 2027 and will cost less than the top pitchers in free agency.
Sandy Alcantara, SP
12Sep 23, 2026; Chicago, Illinois, USA; Miami Marlins pitcher Sandy Alcantara (22) celebrates after defeating the Chicago Cubs after the ninth inning at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images
There have been rumblings over the last couple of years about the Miami Marlins trading Sandy Alcantara. However, they held on to the 2022 Cy Young and hoped that in 2026 he could prove he was fully recovered from Tommy John surgery to boost his value. But while he was better this season (13-11 record), he still had an ERA near four (3.87).
It all means the Marlins might more seriously consider a trade this offseason and try to sell the idea that he is nearing his previous All-Star form. Alcantara would certainly be a good addition to the Chicago rotation. The big question is: Do they have good enough prospect assets to get a deal done?
Byron Buxton, OF
12Aug 18, 2026; Minneapolis, Minnesota, USA; Minnesota Twins pinch hitter Byron Buxton (25) celebrates his run against the Atlanta Braves in the eighth inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images
Another replacement option for Happ or Suzuki in the winter could be Minnesota Twins veteran Byron Buxton. The three-time All-Star (including this season) was in trade rumors last year, but Minnesota held on to him. After another losing year, the Twins may be more open to trying to get his contract off their books and get a solid prospect return.
The 12-year veteran can help replace the lost numbers on offense, and the one-time Gold Glove winner brings more reliable defense to the outfield.
Pete Fairbanks, RP
12Aug 15, 2026; Cincinnati, Ohio, USA; Miami Marlins relief pitcher Pete Fairbanks (29) pitches against the Cincinnati Reds in the ninth inning at Great American Ball Park. Mandatory Credit: Katie Stratman-Imagn Images
One last name that should be on Chicago’s radar as an addition to the bullpen is eight-year veteran Pete Fairbanks. And that is because he might come at a surprisingly low price this winter. Since 2022, Fairbanks has been one of the better relievers in baseball and has tallied 20 or more saves three times. However, he had a miserable season in 2026 as he posted a 6.31 ERA for the Marlins.
A major reason why was nerve irritation and numbness in his throwing arm, for which he had season-ending surgery for late in the year. If medical evaluations show he can return to the player he was for the last few years the Cubs should take a hard look at signing him in free agency.
After earning his journalism degree in 2017, Jason Burgos served as a contributor to several sites, including MMA Sucka … More about Jason Burgos