Chicago Cubs: Looking ahead: Who gets the first extension?

Kris Bryant

The best player on the team, a Bryant extension won’t come cheap. Tom Verducci of Sports Illustrated said extension talks this offseason “went nowhere” and Bryant himself said he’s focused on ‘playing it out’ rather than worrying about any deal.

Pros: Bryant is a monster, plain and simple. His first two big-league seasons rank among the best for any player ever. Without him, the Cubs don’t win a World Series. An extension will almost definitely be a record-setting one, but it’ll also definitely be worth it for the franchise.

Cons: Like Russell, Bryant’s agent is Boras, so the MVP will most likely hit free agency, unless the extension is one he can’t refuse. With Bryant it’s not why he shouldn’t get an extension, it’s more a matter of how.