Yesterday, in the bottom of the sixth inning, Ian Happ hit his first home run of the 2026 regular season, a three-run shot (as a righty) with two outs off Ken Waldichuk. That was also his 174th homer in the big leagues, all of which have come as a member of the Chicago Cubs.
And, as it turns out, that was a pretty notable milestone for the franchise, as Ian Happ is now tied with Andre Dawson for the 14th most homers in franchise history. Andre Freakin’ Dawson.
But here’s the thing, there are a few more rungs on this ladder Happ can climb before the end of the season, when he becomes a free agent. And that means we have a little something extra to track this year:
Cubs All-Time HR Leaderboard:
Sammy Sosa: 545 HRs Ernie Banks: 512 HRs Billy Williams: 392 HRs Ron Santon: 337 HRs Ryne Sandberg: 282 HRs Anthony Rizzo: 242 HRs Aramis Ramirez: 239 HRs Gabby Hartnett: 231 HRs Bill Nicholson: 205 HRs Hank Sauer: 198 HRs Hack Wilson: 190 HRs Alfonso Soriano: 181 HRs Derrek Lee: 179 HRs Ian Happ: 174 HRs Andre Dawson: 174 HRsWith just five more homers this season, Happ will match Derek Lee at 179. With seven more, he catches Alfonso Soriano at 181. With 16 more and he’s tied with Hack Wilson at 190. And with 24 more homers this year (25 total), he’ll enter the top-10 among all Chicago Cubs in franchise history. That’s incredible, especially for a guy with four consecutive Gold Glove awards in left field.
So how likely is that to happen? Well, let’s look backwards to see.
Ian Happ HRs x Season:
2017: 24 HRs 2018: 15 HRs 2019: 11 HRs 2020: 12 HRs (short season) 2021: 25 HRs 2022: 17 HRs 2023: 21 HRs 2024: 25 HRs 2025: 23 HRsAs you can see, 25 is pretty much the top-end of homers in a good Happ year. He was really hurt by that short 2020 season, because that was actually BY FAR his best home run to fly ball ratio. If they played more than 60 games that year, he might already be at or very near the top-10. Alas.
But, hey, he could still do it. ZiPS projects him to hit just 22 long balls this year, which would leave him a little short of the top-10. Of course, this is all assuming the Cubs don’t bring him back after the season.
As a reminder, 2026 is the final year of Ian Happ’s three-year contract extension, making him a free agent this winter. And it’s not really clear whether the Cubs are all that interested in keeping him in Chicago for his entire career, as is his wish. They did just lock up a couple of other players on extensions, though, so maybe they’ll want to keep the good times rolling.
And it’s not like there’s not a TON of money coming off the books as is:
Money coming off #Cubs books at the end of this season (luxury tax): Imanaga: $22.025MHapp: $20.3MSuzuki: $17MTaillon: $17MBoyd: $14.5MRea: $6.5M*Harvey: $6MKelly: $5.75MThielbar: $4.5MMilner: $3.75MCarlson: $2MConforto: $2MWebb: $1.5M*Austin: $1.5MTotal:…
— Michael Cerami (@Michael_Cerami) March 28, 2026The issue, however, is that the Cubs also have another outfielder, Seiya Suzuki, poised to hit free agency. And they could be grooming Matt Shaw to be an outfielder long-term, now that the entire infield is locked up for at least the next four seasons. And that goes without mentioning Kevin Alcantara, whom they still hope can unlock his immense upside.
Way back in January, I explored some comps for an Ian Happ extension, though this assumes just a typical or slightly below typical Ian Happ year in 2026. If he gets better or more consistent, there’s reason to believe he could get much more than this. Walk year performance is important. No big news there.
Ian Happ Extension Comps
Looking back at the last six years of free agency, a few comps stand out:
2022 Chris Taylor
Age: 31 Season before FA: 2.8 WAR Qualifying Offer: Rejected Signed: 4 years, $60M (Dodgers)Relative to Ian Happ: Way more defensively versatile, one year younger, worse offensive upside/consistency.
2023 Joc PedersonAge: 31Season before FA: 2.4 WARQualifying Offer: AcceptedSigned: 1 year, $19.65M (Giants)
Relative to Ian Happ: Coming off a monster offensive season, but an absolute black hole defensively and extremely rough vs left-handed pitching.
2025 Teoscar HernadezAge: 32Season before FA: 3.4 WARQualifying Offer: RejectedSigned: 3 years, $66M (Dodgers)
Relative to Ian Happ: Better offensive walk year, much higher realized offensive career, more power, worse defensively.
To me, this boils down to the following ask in free agency (again, assuming a normal Ian Happ year in 2026).
Years:
Absolute ceiling (unlikely): 4 years Should ask for: 3 years Should get at least: 2 yearsTotal Guarantee:
Absolute ceiling (unlikely): $60M Should ask for: $39 Should get at least: $30MWorking in Happ’s favor is that he’ll be hitting free agency after a new CBA is reached, which should provide rules and financial certainty for all interested front offices. He’ll also be heading into just his age-32 season, which is still on the right side of “yeah, he’ll get one more multi-year deal, assuming all goes well.”
And, don’t get me wrong, if he somehow has a monster season in 2026, following so many years of consistency, you can throw this all away. In that scenario, he certainly could get a lot more. But I think the most likely outcome is just another typical Happ year, which has, well, the sort of value I laid out above.
In terms of an extension with the Cubs right now, then, I’d guess the most he’d be realistically able to tack on is two years (maybe 1+team option) after 2026. So, given that makes $19M in 2026, maybe a REALISTIC FOR THE CUBS new deal that starts immediately (i.e., replaces 2026) is something like: 3 years, 45M (i.e., tacking on two years and $26M in new money to keep him in Chicago through 2028).
OR, more likely, something that includes just one more guaranteed year, but another club option/buyout for 2028. Think something like two years, $35M with a $5M buyout and $15M club option for 2028.
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I think Ian Happ would call the above proposals low, and it’s not difficult to see why. At the same time, the Cubs have so far not shown a particular interest in going big on an extension with him, and they have dolled out a fair bit of cash already lately. So when I was coming up with those numbers, it was more about what could REALISTICALLY be appealing to the Cubs and potentially acceptable to Happ, not what I think Happ might be able to command on an open market with a fresh CBA in place. It might come down to how badly he wants to stay in Chicago.
Ultimately, I think this will be one of those negotiations that actually makes it to free agency, but where both the team and the player do have some interest in sticking together. Happ has made Chicago his home and has routinely indicated how badly he’d like to be a Cub for life. And given how good he’s been year in and year out (and the fact that he’s a great defensive outfielder who can switch-hit), the Cubs should probably try to find a way to make that happen.
Until then, however, let’s root for at least 25 homers this season. It would be a very nice feather in the cap of the Cubs very successful 2015 first-round pick.
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