Chicago Cubs star outfielder Ian Happ has opened up about the chance of returning to the team for the 2027 season. The slugger is set to become a free agent as his three-year, $61 million contract expires. During his decade in Chicago, the star became an All-Star, a four-time Gold Glove winner, and a leader in the clubhouse. Despite this, a pending breakup seems fairly likely.
Cubs president of baseball operations Jed Hoyer recently claimed that “everything’s on the table” regarding Happ. The star also previously tossed a baseball with beer money attached to it into the Wrigley Field bleachers during the team’s final regular-season home game. The All-Star outfielder certainly knows he could have played his last game for Chicago.
Happ has since made an appearance on The Rahimi & Grote Show to discuss his future. Mark Grote specifically asked the pending free agent about his chances of returning to the Chicago Cubs. “That’s a good question,” replied Happ. “I don’t have any answers about it right now.”
“Obviously, like I’ve said, I’ve loved my time in Chicago. It’s been amazing. The free agency process, it’s not something that I’ve been through before. I was lucky enough to sign the extension before having to go through the process earlier in my career. So I don’t really know what the process holds or how it’s going to play out.”
Chicago Cubs Could Already Have Ian Happ Replacement in Mind
Happ went on to admit that the Chicago Cubs “have a bunch of different directions they can go in” regarding offseason moves. This is certainly true. After all, Hoyer and Co. have several key players heading towards free agency. Along with the outfielder, Chicago will also have to figure out the futures of Seiya Suzuki, Shota Imanaga, Kevin Gausman, and most likely Clay Holmes.
Because these three starting pitchers make the list, the Cubs are expected to spend a significant portion of their funds on strengthening their rotation. If true, Chicago could very well deploy Pedro Ramirez in Happ’s typical place in left field. The Cubs are known to be extremely high on the versatile rookie. Going this route would save the organization money to put towards starting pitching.
The Chicago Cubs have also been linked to a trade for Cleveland Guardians star Steven Kwan to replace Happ. While he is a proven MLB veteran, Kwan is expected to only earn around $10 million in 2027. Replacing a four-time Gold Glove winner with another would be a smart move by Chicago.
Chicago Unlikely to Reward Hitter This Winter
While neither Happ nor the Chicago Cubs are closing the door on an extension, a reunion seems unlikely. According to Spotrac, the star slugger was the fifth-highest paid left fielder in baseball in 2026. While he somewhat underperformed his usual offensive output this season, the veteran will likely look for a substantial salary this winter.
Chicago, however, is not expected to give out a big contract to a hitter in the coming months. Happ has also talked about the Cubs in the past tense, and he told The Rahimi & Grote Show that he is excited and interested to see how the free agency process pans out.
Cubs Star Ian Happ Hints at Future Plan as $61 Million Deal Ends