Ian Happ is a free agent after the 2026 season. It seems like he may be preparing for a post-Cubs career elsewhere.

Entering the 10th year of his big league career, Ian Happ is the longest tenured Chicago Cubs player on the roster. Happ has spent his entire career on the North Side of Chicago. However, 2026 may be his last calling Wrigley Field home.

Happ was a first-round draft pick by the Cubs in 2015, making his MLB debut in 2017. Since then, he has played 1,139 games for the Cubs. Happ has won four consecutive Gold Glove Awards in left field and made an appearance in the All-Star game in 2022. During the 2023 season, Happ signed a contract extension with the Cubs, avoiding free agency and keeping him in Chicago for three additional years.

At the end of 2026, Happ will become a free agent. He will be free to sign with any team that offers him a contract. While the Cubs may still be in play to retain him and keep him in Chicago, Happ seems to be preparing for the possibility of moving on.

Ian Happ Hints Cubs May Not Be in His Market; “Plausible” He Plays Elsewhere After 2026

Last week, MLB insider Bruce Levine asked Chicago Cubs left fielder Ian Happ about free agency and what could happen. Happ says it is “plausible” that he plays elsewhere after the 2026 season.

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However, Cubs beat reporter Sahadev Sharma from The Athletic (subscription required) reports that Happ is completely focused on winning this year, and the focus is on this team. Happ says going into his walk year is “a lot easier” because he is part of a good team.

The Cubs will indeed be good this year. Coming off their first postseason appearance since 2020 (if you even want to count that), the Cubs are the favorites to win the division and make a deep run in October. Happ, just as he’s done before, will quietly be a key contributor for the Cubs and their success. After 2026, though, one of the most underappreciated Cubs of this generation may take his talents elsewhere.