#2. Ian Happ
Ian Happ has been one of the few Cubs players living up to expectations of late. In a depressed offensive season across the league, his .229/.345/.419 slash line is good for a 120 wRC+. Since the start of May, he's also been one of the few sources of slugging on this roster with a .237/.352/.480 line and a 136 wRC+. He's not grading out as the Gold Glove defender he was in 2022, but his bat could be a big upgrade for a team with an open corner outfield spot.
The rub, again, is the contract. The Cubs inked Happ to an extension last season that pays him $20 million this year and next followed by $18 million in 2026. That is a big expenditure for a left fielder who isn't always a difference-maker on offense, but eating a bit of money could sweeten the deal. Even harder to overcome, however, is his no-trade clause allowing him to veto any deal if he'd rather not leave Chicago.
If they can get over both hurdles, however, he's shaping up as one of their best pieces to dangle at the deadline while shaking up the Cubs' core. Moreover, they can afford to lose pieces from the outfield this season with Owen Caissie getting very close and Alexander Canario deserving of another shot. Such a move would leave questions for 2025, but everything needs to be considered for the right offer if it can help put this organization back on the rails.