Cubs should roll the dice and get an extension done now
Which players Jed Hoyer and the Cubs will keep for the future remains to be seen. Whether it’s Bryant, Baez, Contreras or Rizzo, each will likely be paid a large amount in a long-term deal.
Maybe they can’t keep them all but think about this for a second. It’s hard enough to put a number on each player now. The difficulty will increase at the end of this season if each player performs at a high level. Besides Contreras, each player will hit the free agent market, where other teams will make their bids.
That’s why I say extend at least one of those players now. There’s a chance each player and their agents will wait out the season, so they receive a larger payday, but if there’s a possibility to reach an agreement now I think it’s worth the gamble.
From both the perspective of the front office and that of the players, waiting out the 2021 season will be a risk. I’m not projecting this as his worth or what he’s asking for, but let’s say Bryant and the Cubs agree on a two-year, $50 million extension. If Bryant underperforms, it’ll be viewed as too much money spent. If Bryant plays at an MVP-level, he will likely be looking for an offer somewhere in the Nolan Arenado range (eight-year, $260 million).