2. Ian Happ
Oh, people are not going to like this one. Look, I love Ian Happ just as much as the next Cubs fan, but the reality is his contract is expiring at the end of the year. While he has emerged as a leader and is a fan-favorite, it probably will not be worth it to re-up on a switch-hitting outfielder, who will be 29 years old at the time of his free agency. This team needs a long-term, power-hitting corner outfielder, and Happ has never been able to exceed 25 home runs, and at times his power numbers have been pretty bad. 25 home runs are nothing to complain about, but doing that once every four or five years is not going to cut it. I think giving him a large contract when you have several power-hitting outfielders on your top-ten prospect list would be unwise.
I would rather see the Cubs invest in Nico Hoerner long-term while seeing what you can get for Happ at the deadline if he is performing well enough. Happ's stock is also high right now, as he is fresh off winning a gold glove and leading the Cubs in 2022 with 72 RBI. He is a versatile player that could fetch the Cubs a decent prospect or two at the 2023 deadline if a playoff run does not look likely.