Will the Cubs once again look to trade Ian Happ this offseason?

Despite the standing ovations and dugout hugs that transpired in the days leading up to this year’s Aug. 2 trade deadline, both Willson Contreras and Ian Happ finished the year with the Cubs.

Contreras now looks likely to reject the qualifying offer Chicago plans on extending, hitting free agency for the first time in his career. The three-time All-Star remains one of the best offensive backstops in the game, but faces questions about his work behind the dish.

Cubs have multiple options when it comes to Ian Happ

As for Happ, there are three paths forward:

1. The Cubs attempt to work out a long-term extension with the switch-hitting outfielder this winter.
2. Jed Hoyer shops Happ on the trade market, potentially in a deal to add a frontline starting pitcher like Pablo Lopez or Shane Bieber.
3. Much like they did with Contreras this summer, the Cubs take a wait-and-see approach and re-evaluate where things are at ahead of the 2023 deadline.

We’ve heard rumors the Cubs will look to extend Happ and/or Nico Hoerner this winter already, but if those talks fail to go anywhere, a Happ trade can’t be ruled out given the relative weakness of this winter’s class of free agent outfielders.

"“We’ve taken the first steps,” Hoyer told 670 The Score, when asked about Happ and Hoerner. “As you guys know, we’re not going to talk about it once we do (get more in depth). But certainly there are players that we’d love to keep in a Cubs uniform for a long time. Hopefully we can work hard on those and get some across the finish line.”"

Brandon Nimmo and Andrew Benintendi stand out as the top free agent outfielders not named Aaron Judge this winter and you can bet the Mets will do everything they can to retain the former. That could allow Hoyer to net a strong return for the final year of Happ, who is coming off a quietly impressive 2022 performance.

While him home run output was down, Happ smacked a career-high 42 doubles this year for Chicago, slashing .271/.342/.440 – good for a 119 OPS+. The front office couldn’t find the right deal for him at the deadline, which wasn’t a big deal given he’s under contract through the 2023 campaign.

The Cubs moved on from Jason Heyward at season’s end, choosing to pay out the last year of his deal, while giving the veteran a chance to latch on with a new club this winter. That leaves Seiya Suzuki in right field, assuming he’s on the roster come spring, Happ in left, and some combination of Nelson Velazquez and Christopher Morel in center.

We’ve talked a lot about starting pitching, shortstop and first base when looking ahead at the Cubs’ offseason plans, but don’t rule out an outfield upgrade, either. It almost becomes a ‘must’ if you trade Happ, although top prospect Brennen Davis will almost certainly make his big league debut next season.

You’re not going to move Happ just for the sake of moving him, but as we talked about recently, you need trades to build a championship contender – and if the market favors such a move, the Cubs won’t hesitate to send their All-Star outfielder packing.