There is value in keeping some young players cheap, but at some point they can price out the future. It’s a risk but so is free agency. The one extension everyone questioned was Rafaela, but right now that looks like the best one.
Bregman is 32, and signed through age 36 and hasn’t been the same player he was in 2017-19 since, well, 2019. Chances are very good he continues to decline over the next 5 seasons and is no longer “good” before they end.
With free agency, you need to get the good years upfront or you’re f***ed. With extensions, you still have a chance if the player doesn’t hit the ground running…