Cubs Facing Big Decision After Ian Happ's Comments

Chicago Cubs star outfielder Ian Happ is set to enter MLB free agency following the 2026 MLB season. The 31-year-old has spent his entire career in Chicago with the Cubs, but there is a chance that 2026 will be his final year with the ball club. Happ recently commented on his upcoming free agency, via Bruce Levine.

"It’s been a true honor for me to represent this great city, organization and fan base," Happ said. "The reality of this is, you can’t control if the team wants you back. It's totally plausible another chapter elsewhere awaits me."

Seeing Happ in a different uniform would feel strange. He has played with the Cubs since 2017. As he said, there is a chance that he could end up "elsewhere" given his upcoming free agency.

Will the Cubs re-sign him? Or, will Chicago attempt to sign him to a contract extension?

Cubs Could Offer Ian Happ a Contract Extension

The Cubs have built a quality core of players. Happ is among the guys who Chicago has built around. Losing him to another team would be far from ideal. It goes beyond strictly performance with Happ, as he's become a leader as well.

As far as his performance is concerned, Happ's offensive numbers have been up and down in recent years. He was an All-Star in 2022. In 2025, he hit just .243 across 150 games played. He did record a .762 OPS, 23 home runs and 32 doubles, however.

Happ's value only increases when it comes to his defense. He has won four consecutive Gold Glove awards. The Cubs are consistently able to rely upon Happ in the outfield. He has become one of the better defensive players in all of MLB.

There was a time when Happ was a utility player, spending time in the infield in addition to the outfield. Over the past few years, Happ has primarily handled duties in left field. It has been a good decision, as he's impressed at the position to say the least.

Will the Cubs bring Happ back? If he enters free agency, the chances of a reunion will become slim. The veteran is going to draw plenty of interest next offseason. The Cubs' best chance at keeping Happ for the long-term future will be via a contract extension.

They need to decide if they will discuss a potential deal with Ian Happ, though.