What Would Ian Happ Extension Have to Look Like for Both Sides to Agree?

The comprehensive roster churn of the last five years on the North Side is nearly enough to have created a Mandela Effect when it comes to Ian Happ. So as legions of Cubs fans spent much of Wednesday and very early Thursday celebrating the sixth anniversary of the greatest sports moment of their lives, I had to keep reminding myself that Ian Happ wasn’t part of that team.

Not only did he miss out on being bestowed with irrevocable legend status as a World Series winner, but he also flew under the radar when talk turned to extending the core. Happ has always been an above-average producer, sometimes barely so, and never really spurred the team to make a decision on his future one way or the other.

That included this year’s trade deadline, up to which the Cubs were shopping their switch-hitting left fielder with the intent to move him. He and Willson Contreras said their goodbyes to one another, their teammates, and the fans, then both were back at Wrigley when offers didn’t match Jed Hoyer’s asking prices. Now Happ is an All-Star and Gold Glove winner who looks like he could help to anchor a much better lineup.

Not that accolades alone are enough to get a new deal done.

“I can’t say that this one thing is going to be the determining factor of that,” Happ told reporters in the wake of his Gold Glove win. “But I will say that just putting together a whole year, putting together both on the offensive and defensive side and the consistency from both sides of the plate, all those things give me a chance to be somewhere long term.”

Happ has maintained all along that he’d prefer to stay with the Cubs, the only professional organization he’s known since being drafted ninth overall in 2015. He’s built a life in Chicago and his bond with the fans is obvious, but he’s also a pragmatic union rep who understands the way the business works.

“I’ve always been up-front about the fact that I love it here,” Happ said. “I love the organization, I love the people — coaches and teammates and people in the city that have made my time here really special.”

No matter how many times he repeats it, hope alone isn’t enough to keep Happ in a Cubs uniform. It isn’t overriding his desire to capitalize on a big year in what might be his only shot at free agency, nor will it spur the Cubs to soften in their reluctance to meet those same desires by previous stars. The big difference in this case is that Happ just finished the best season of his career and displayed a greater degree of consistency at the plate and in the field.

Between the Gold Glove and injuries to two of the Cubs’ top outfield prospects, Hoyer might have a little more motivation to firm up the foundation of his Next Great Cubs Team. Then again, Hoyer might see this as a way to increase the asking price for Happ as part of a roster overhaul this winter. What direction they choose to take comes down to how much faith the team has in Happ’s ability to continue being this player long-term.

That will be reflected in what kind of offer they extend, assuming there’s a willingness on the part of the front office to negotiate at all. Happ has just one year remaining on his rookie deal and he figures to make around $10-11 million via arbitration in his age-28 season, so there’s really no discount for buying out arb years. The Cubs have indicated a desire to limit contract durations and it feels like going beyond five years is out of the question.

Would something like five years at $75 million be enough to get it done? Including the arb year at $11 million, that would be another $64 million over four years of “new” money ($16M AAV). That’s probably a little light for Happ, but how about the same length at $87 million and at least a partial no-trade clause and some performance incentives?

Getting $19 million annually in new money plus the security from the NTC means Happ can avoid reliving the anxiety of this past deadline. The duration means the Cubs get the remaining prime years of Happ’s production while he can test the market again heading into his age-33 season, at which point he might still be able to land another decent contract.

There’s some wiggle room in between those figures above and I could see something closer to the higher end making sense for both sides. But even if everyone involved is amenable to the concept of an extension, we might have to wait right up to the very end of spring training for something to get done. The Cubs will prioritize additions via free agency and trades, with the resultant haul determining how much they’ve got left in the budget for current players.

“Maybe there’ll be something down the road, but it’s their job to look at all possible outcomes and the way that that shapes their thinking for not only free agency and trades but long-term internally,” Happ said.

Though Hoyer obviously hasn’t come out and said it directly, indications are that a new deal for Nico Hoerner will take precedence over an extension for Happ. The organization will also want to see how its cadre of young outfielders perform this spring, as that collective development process could well determine exactly how the Cubs value Happ beyond 2023. All of which is to say Happ is absolutely correct about the Gold Glove not being much of a factor.

I can see a deal being worked out, but I think the path to it happening is winding and marked by more than a few forks that will have to be navigated in tandem. With so many opportunities for team and player to diverge, the likelihood of them arriving at the same destination feels anything but assured.

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