Chicago Cubs News: What an Ian Happ extension will look like

The most challenging road to navigate this winter is how the Chicago Cubs want to proceed with Ian Happ. After coming off an All-Star and Gold Glove season, the switch-hitter's value is at a strange middle ground where if he keeps playing as he did in 2022, he could easily be one of the more sought-after bats in free agency next season.

On the other hand, Happ has been inconsistent throughout his career until the 2nd half of 2021. The reality, though, is we're almost two years removed from any Happ inconsistencies. He has turned a corner and deserves to get paid a handsome salary. Although he has stated that he wants to be in a Cubs uniform long-term, more often than not, money talks.

After Rafael Devers was extended to a long-term deal with Boston, next year's free agent market further deteriorated with top-of-the-line bats. Aside from Shohei Ohtani and Manny Machado (assuming he opts out or doesn't get extended), Happ is right up there with anyone else as a top target next winter.

From a common sense standpoint, the front office obviously wants to avoid seeing Happ walk in free agency next year. The predicament is the Cubs are trying to compete now, and if that is the case come summertime, they won't want to trade him either. Therefore, a very real and unfortunate reality here is that it's either an extension or he walks for free with nothing more than a qualifying offer that is detrimental for him to accept at that point. Michael Cerami of Bleacher Nation wrote up a solid piece on even more reasons the Cubs should bet on Happ.

Unless he is genuinely willing to take a team-friendly deal, the Cubs will have to up the ante considerably. The two sides could respectfully agree to let talks wait to see how things play out for Happ in 2023 until just before the season ends to reasonably determine his value over an even bigger block of work. So if something doesn't get done soon, it doesn't necessarily mean it won't happen at some point.

Chicago Cubs: What would the front office have to do to make it work?

If the Cubs can land Happ on an extension before the arbitration hearings commence, it will likely be structured with a lower AAV for 2023. With all the money coming off the books next season (Heyward, Hendricks? Stroman?), the finances are there for a higher price tag in 2024 for Happ than they are this season. The Cubs presumably still want to add another bat or bullpen depth. If they're going to stay under the luxury tax, which they should, adding a reliever or bat and a big contract for Happ this season starts to become unrealistic if they want to have funds available for the trade deadline.

The fact that top-tier bats are limited next winter is a double-edged sword because where Happ can use that to his advantage, Jed Hoyer may want to avoid missing on bats like he did this year with certain players. Knowing Happ will get a substantial payday if he has any type of good season, which I think we can agree he at least should, needs to be enough for Hoyer to know the market and sign him now. The Cubs must also break the stigma that they never extend home-grown talent. We've seen Kris Bryant, Javy Baez, and Willson Contreras all leave the organization without a contract extension.

Elsewhere, keeping Happ opens up trade scenarios regarding one of the Cubs' outfield prospects, such as Owen Caissie or Kevin Alcantara. We know Pete Crow-Armstrong is a center fielder who Happ wouldn't block. The health uncertainties around Brennen Davis and Alexander Canario are too ominous to assume they will be everyday contributors at the top level. You're then left with two outfield prospects who are a couple of years away when the Cubs openly state they want to win now. There is no sense in letting Happ go, hoping that Canario or Davis will work out and excel to the point Happ is already at, anyway, especially when you have the resources to pay a guy like Happ moving forward.

Can Andrew Benintendi's contract for five years/$ 75MM be a starting point? We're at a point where we have to consider north of that. Happ has more pop in his bat, and if he puts it together with the home runs and batting average this season, he is worth substantially more. If he chooses to bet on himself, there's reason to believe that an offer of five/$85MM wouldn't even be enough to make him ink his name, knowing what he can garner in a bidding war next offseason if he has another all-star campaign.

Projection to get it done: 5 years, 90.0MM, 18MM AAV.