Cubs face an awfully tough decision when it comes to Ian Happ
There are a lot of variables for the team to consider going into the deadline. They may be hesitant to extend Happ because,, while this has been inarguably the best stretch of his career, it’s only been half a season and there have been large stretches of Happ’s career that look encouraging only for them to be followed by equally lengthy periods rife with struggle. It also always takes two to get a deal done and Happ may be more inclined to hit the open market rather than taking an extension at this stage.
On the other side of the coin, the Cubs are likely to be more hesitant about trading Happ due to the fact that he’s been a force offensively and could be a big help on a more competitive 2023 team. It’s been reported Chicago will be big spenders in the coming offseason in an effort to be more competitive, and trading Happ would make that a more difficult task. Many are also reporting that a Happ deal still appears unlikely.
The one certainty with the Happ situation is that it seems unlikely that Jed Hoyer would force a trade of the veteran outfielder. Unlike with Contreras or anyone else traded recently, Hoyer has the luxury of having more team control with Happ so the Cubs don’t have to play their hand if they don’t want to. It’ll likely take a deal that blows the front office away to pry Happ away, but what team would be willing to do that, and what could such a trade look like?
For the best answer to this question, the Cubs should look to the Bronx for their ideal Happ suitor. The Yankees seem likely to move Joey Gallo at the deadline which would slot Aaron Hicks in as a starter, so it’s likely they’ll look for an upgrade in the outfield once again. Fittingly enough, that Gallo trade is a good baseline to start with for a trade that sends Happ to New York.