Several Factors Make Ian Happ Extension Far From Likely

Jed Hoyer has talked more than once about having in-house candidates he’d like to extend and he’s also stated that he’d prefer to have negotiations complete prior to spring training. Among other factors, that timeline may complicate matters when it comes to the possibility of working out a new deal with Ian Happ. While the Gold Glove left fielder has reiterated a desire to remain in Chicago, his savvy and responsibility as the team’s union rep mean he’s probably not open to taking much of a hometown discount.

Sahadev Sharma predicted Happ would end 2023 in a different uniform, though not via trade. In similar fashion to how the Cubs never really engaged Willson Contreras in a meaningful way, the club and Happ may simply end up with disparate valuations. Just as Contreras and his reps probably targeted the J.T. Realmuto deal rather than trying to beat Yasmani Grandal‘s, Happ may be looking at what Brandon Nimmo got instead of starting from Andrew Benintendi‘s Sox contract as a baseline.

Contreras did end up beating Grandal’s deal in terms of time and total value, but the White Sox catcher has a higher AAV. Between Contreras likely seeking even more in the early going and the Cubs already looking to move in a different direction behind the plate, there was simply too much ground to cover for something to work out.

Likewise, Happ coming to the table with anything close to the eight-year, $162 million Nimmo got from the Mets would put the kibosh on a swift agreement. It’s hard to imagine the Cubs being willing to stretch into nine figures, at least not fully guaranteed, so the chances of anything getting done during the spring are slim. Unless Happ is willing to carry talks into the regular season, or unless his ask is much lower, we get back to the Contreras situation.

The Cubs are also going to want to see what happens with their young outfielders in the early going, as that’s going to determine their willingness to pay Happ long-term. Brennen Davis is reportedly doing well and shouldn’t be impacted further by the stress reaction that shelved him during Arizona Fall League play. Alexander Canario is recovering from a nasty broken ankle and could return by mid-season, then the Cubs have Kevin Alcántara and Owen Caissie making noise.

The question will be whether the organization believes any of those players can be more valuable than Happ over the next 5-6 years, a proposition that will be heavily influenced by cost. After all, getting similar production at around $20 million less per season produces far more value and frees up even more room for bigger additions like Rafael Devers or Shohei Ohtani. While those acquisitions are far from guaranteed, the first part of the equation is a little easier to solve.

Just like the Cubs have little urgency due to their up-and-coming prospects, Happ will almost certainly not be in a rush to sign quickly. The longer it goes with neither side pushing to get something done, the more likely it becomes that nothing ever does. That shouldn’t come as any surprise because it’s pretty much been the Cubs’ MO with extension talks all along.

Now, there’s a case to be made that securing Happ for the next half-decade or so provides stability in the field and the lineup while creating flexibility for Hoyer to make moves with those young outfielders. Paying for a little more certainty than they’d have with prospects might be worthwhile, though, again, the Cubs might prefer to may a big splash elsewhere while replacing Happ from within.

I won’t be surprised if something does end up being worked out, but I’ll be even less surprised if this ends with both sides kind of shrugging their shoulders and saying, “Welp, we just couldn’t get anything done.”