Addison Russell
Russell is a defensive stud and is a budding power bat. Drilling 21 homers and driving in 95 runs as a 22-year-old shortstop is impressive, and he’s definitely going to get better. An extension now would be very expensive, but could be worth it.
Pros: Russell is already extremely important to the Cubs. He’s only going to get better and, like Báez, locking him up now could save big money long-term. He’s proven himself as a threat at the plate and is one of the best defensive infielders in all of baseball.
Cons: Russell’s agent is Scott Boras, who’s notorious for getting his clients to free agency. Unless the extension is massive, it looks like the young shortstop will reach the open market.