Cubs must decide whether to trade or extend a breakout Ian Happ

Anyone who’s played MLB The Show in recent years, knows that almost every time Ian Happ steps to the plate, he’s referred to as ‘Pittsburgh area native, Ian Happ’. Clearly, the Cubs outfielder loves facing the Pirates – he’s got a .979 OPS against them in his career.

This week, Happ went 5-for-16 with a home run, two doubles and a pair of runs, despite the Cubs dropping three-of-four to Pittsburgh. That aligned with the first update on All-Star Game voting which, despite his breakout season, finds Happ on the outside looking in when it comes to making the National League team next month.

Among NL outfielders, only Mookie Betts carries a better OPS than Happ this year, who has been buoyed by a torrid pace here in June. The switch-hitting Happ is batting .368/.443/.605, emerging as a force for a Cubs team searching for answers after losing 13 of its last 17 games. With the trade deadline looming, Jed Hoyer faces a tough decision: do you trade Happ with one-plus year of team control left, when his value is higher than ever before, or is now the time to extend him?

As we know, the Cubs haven’t been successful at locking guys up to extensions – you can delve into the ‘why’ for days, but the end result remains the same: a lack of homegrown players sticking around once their arb years pass. The money is surely there, but are you paying Happ for what he’s doing here in 2022 or the ups and downs that, at one point last year, had him looking like a non-tender candidate?

Cubs have reinforcements on the way in the outfield

Chicago’s prospect rankings are littered with outfielders: according to MLB Pipeline, Brennen Davis, Pete Crow-Armstrong, Kevin Alcantara and Owen Caissie all rank in the organization’s top 10 list. Obviously, at the big league level, you’ll have Seiya Suzuki for the foreseeable future, as well, and free agency could always further bolster the outfield mix.

In other words, there’s going to be options for Ross in the outfield with or without Happ. Really, the decision over whether to trade or extend him will come down to what timeline the front office is working off. If they have no intention of drastically improving the club and returning to the postseason heading into 2023, then trade him now, when you could dangle one of the best outfielders in the league and get a massive haul in return.

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We know Willson Contreras is as good as gone but, for whatever reason, there’s been far less speculation regarding Happ. If the team isn’t thinking extension, now is the time to trade him – especially given his absolutely scorching hot month of June that warrants Player of the Month consideration.