Can Ian Happ become one of the Cubs all-time home run leaders?

Ian Happ has 102 career homers, and because he’s never played anywhere else that means 102 with the Chicago Cubs. That puts him 25th on the team’s all-time homer leaderboard. Now “25th” may not sound all that impressive, but bear in mind this is a franchise that began its existence three decades before the advent of powered flight. There are a lot of guys who have hit at least one dinger for the Cubs, and Happ is already in the top 25. Right now he’s just behind Rick Monday (106) and just ahead of Keith Moreland (102) on the all-time list. How high could he rise?

The premise of this post is, of course, that the Cubs will sign Happ to an extension, a highly uncertain proposition. Happ wants to stay (subscription required), and most fans probably agree, but Jed Hoyer’s vote is the one that matters, and he’s given little direct indication one way or the other. That Hoyer was prepared to trade Happ for the right offer might suggest Happ won’t get an extension, but virtually every player on every team is available for “the right offer,” so that may not tell us much.

You learned why extending Happ would make sense in this space back in May, and these reasons are still valid. Kyle Schwarber’s recent free agent deal with the Phightin’ Phils (4 years/$79M) provides a potential benchmark for a Happ extension. When Schwarber signed that deal he had completed his age 28 season, amassing a 119 career wRC+ with entertaining, if not always effective defense. If the Cubs extended Happ in the winter, that would come after his age 27 season with a career wRC+ of around 114.

Defensive metrics offer a mixed assessment of Happ but he’s shown progress in left this year and can still play other positions in a pinch. Happ has played everywhere except catcher and short in his major league career, and while he’s not a true Zobristian Swiss army knife, he offers a lot more versatility than Schwarber. On the other hand, Schwarber’s Statcast card is drenched in red, while Happ’s most certainly is not. Also, if the Cubs extend Happ in the winter they’ll be buying out his last arbitration year, which probably leads to a bit lower AAV than if they were fishing Happ from the free agent pool.

One final point in Happ’s favor: his much discussed evolution against southpaws. He’s waxing southpaws to the tune of an .865 OPS this season, compared to Schwarber’s.705. But Happ’s progress comes with pockmarks: a 33-to-6 strikeout to walk ratio suggests he hasn’t yet fully mastered the crafty left-handers yet.

Put it all together and a four-year deal somewhere below $79M seems a reasonable guess for a  Happ extension. For purposes of this post we only care about the years, so I won’t spend any more time throwing darts at the salary board – something around $65M wouldn’t surprise me, but something farther away from that figure in either direction wouldn’t surprise me either.

Ian Happ has an outside chance to make Cubs home run history

During his career Happ has averaged 26 homers per 162 games. He’s never actually played a full slate, maxing out at 148 games in 2021. But he’s a durable player who is now an established everyday starter, so assuming he’ll average 148 games a season over the next four years is a reasonable if slightly optimistic guess. His career homer total translates to an average of 23.7 homers per each 148 game season.

So let’s say the Cubs sign Happ to a four-year extension and he averages 24 homers annually. To make things simple we’ll assume he hits no more homers this year, although that’s unlikely. That means Happ would hit 96 more homers with the Cubs, tying him for 10th on the all-time list with Hank Sauer. There is a good chance Happ would pass every currently active player on the Cubs homer list except Anthony Rizzo.

Holy Cow!  Active Cubs home run leaders:

• Anthony Rizzo – 242
• Kris Bryant – 160
• Javier Baez – 140
• Willson Contreras – 115
• Ian Happ – 102

(We could spin out a similar hypothetical involving a Contreras extension, but that seems even less likely than a Happ extension. Also, Willson is three years older and plays a particularly debilitating position, so the results probably would not be quite as impressive.)

Knocking Sauer down the all-time Cubs homer list is not a good reason to extend Ian Happ. But Happ is closer than you might think to securing a place in the Cubs Hall of Fame and, more importantly, he can help the team win a bunch of games on the way there.

If I was playing with real money I’d say Happ will probably be wearing someone else’s City Connect jersey next year. But the chance to see him make Cubs history, one blast deep into the Wrigleyville night at a time, is a good reason to hope otherwise.