What would an Ian Happ contract extension look like?

Ian Happ and the Cubs just settled on a 2023 contract to avoid arbitration:

That’s $250,000 above the MLB Trade Rumors projection for Happ, so actually pretty close to reality. Incidentally, it’ll be the first time since 2020 that the Cubs will not go to an arbitration hearing (Happ in 2021 is the most recent Cub to go to a hearing since then).

The Cubs have talked about signing Happ (and Nico Hoerner) to long-term extensions, but so far, that’s been only talk. It was talked about again at the Cubs Convention last weekend by Cubs President of Baseball Operations Jed Hoyer:

“We have interest in both (Happ and Hoerner), in keeping them long term,” Hoyer said. “We’ve started the process I guess I would say, we’ve had dialogue with the agents. Where that is in the process I would never reveal or what the offers are, but certainly there’s a real desire and we’ve had those meetings with the representatives.”

So yeah... a lot of talk, no action.

That’s certainly not going to stop me from discussing what a possible Happ extension might look like. For an example, we might look at the five-year, $75 million deal Andrew Benintendi just signed with the White Sox. Happ and Benintendi are the same age (29 this year) and were drafted in the same round (first round, 2015).

For a time, it looked like Benintendi would be the better player. From 2017-19 with the Red Sox, he posted a .276/.354/.440 line and hit 49 home runs, stealing 51 bases. Meanwhile, Happ found himself spending much of 2019 at Triple-A Iowa.

But after that injuries hurt Benintendi and Happ broke out with an All-Star, Gold Glove season in 2022 in which he hit 42 doubles. In 2022 Benintendi wound up traded from the Royals to the Yankees, hit just five home runs and had his season ended in early September with a hamate bone injury.

So right at this minute, Happ looks like the better player.

I’m just going to make it simple. Benintendi’s contract includes a 2023 salary of $8 million, then $16.5 million each year from 2024-26 and $14.5 million for 2027. Happ’s should be larger, because, well, he’s the better player. Happ’s making more than Benintendi for 2023, so let’s have him make more in the other years as well.

Five years, $90 million, with a sixth-year team option of $22 million or a $6 million buyout. That would make it a six-year, $112 million deal ($18.67 million AAV) if the team option is exercised, or six years, $96 million ($16 million AAV) if the Cubs make the buyout.

Who says no?

Incidentally, since I’ve made the Happ/Benintendi comparison, I should tell this little story that involves both of them. The first part of the story is this Cubs/Brewers game on Sunday, September 28, 2014, a sunny afternoon game played at Miller Park. Anthony Rizzo went 3-for-4 with a two-run homer and the Cubs won 5-2, thus finishing 2014 with a 73-89 record.

Meanwhile, that afternoon in Boston the Red Sox lost to the Yankees 9-5.

If those two games had gone the other way — in other words, the Cubs losing and the Red Sox winning — the Cubs and Red Sox would have wound up with identical 72-90 records. Had that happened, the Cubs would have drafted ahead of the Red Sox since they had a worse record the previous year (2013). And in that case, the Cubs almost certainly would have selected Benintendi in 2015, as I know they were interested in him on draft day.

Funny thing, now both players will play in Chicago, and hopefully the Cubs extend Happ and they’ll both be in town for a while.