Cubs Rumors: An Ian Happ extension doesn't seem very likely before Opening Day

With Manny Machado off the board after signing a massive extension with the Padres and Shohei Ohtani on a level untouchable by the mere mortals he shares the field with on a daily basis, Cubs outfielder Ian Happ is in a position to score a major payday as one of the top free agent bats poised to hit the open market next offseason.

We've heard for some time now that the front office is interested in extending both Happ and Nico Hoerner, but if I were a betting man, I'd wager the latter has a far better chance of sticking long-term in Chicago than the former, who picked up his first All-Star selection and Gold Glove Award in 2022.

I think all the experiences you have in the game help prepare you. The experience in 2021 of those guys getting traded helped prepare me for going through it in ’22, and then going through that process helped prepare me for any time in the future when I might be involved in those rumors. It’s all part of it.

If the Cubs manage to hammer out the details of a long-term extension before the end of the season, it will almost certainly take the front office getting way out of its comfort zone. Happ's a savvy enough guy to know the dollars that could be available to him in free agency - especially if he can replicate what he did on the field a year ago, posting a 119 OPS+ with 42 doubles.

His earning potential isn't the only factor at play here, though. The Cubs farm system is dripping with outfield talent - headlined by top prospect Pete Crow-Armstrong, Brennen Davis, Kevin Alcantara and Alexander Canario. So it's worth wondering if Jed Hoyer and Carter Hawkins will want to sign someone like Happ to a long-term deal if it means potentially blocking one of those guys. And don't forget that Seiya Suzuki is locked up through 2026 via the contract he signed heading into last year.

Prospects (as Cubs fans know all too well) are far from a sure thing. But we know that developing that consistent pipeline of talent is a top-of-mind focus for the organization and the outfield is a position of strength in that regard. Between the potential logjam moving forward and Happ's potential to net a nine-figure deal in free agency, I'm not overly optimistic about a deal getting done here.