#4 Alex Bregman
Seeing Alex Bregman this low on the list may come as a surprise. It's no fault of his own, but rather, the market. Alex Bregman has been a cornerstone of the Golden Era, and he's one of the top-five third basemen in the MLB.
But is he worth $300 million?
He'll likely command that number, and unless Bregman can tap back into the power stroke he had in 2018 and 2019 (or if the MLB brings back juiced baseballs), he may not be worth that amount.
Alex Bregman absolutely should finish his career as an Astro. If Jim Crane operated as aggressively as John Middleton of the Phillies, it wouldn't be a question. But since Crane pinches pennies, there's no chance of Bregman getting $30 million a year AND any of the above deserving candidates getting their extension.
If Crane wakes up tomorrow and decides to operate entirely differently and spend like the players and fanbase deserve, then yes, lock Alex Bregman up. If you're going to let Kyle Tucker walk the following year, lock him up. But if you do what's right and secure Altuve and Tucker for the future and Crane doesn't undergo a philosophy switch, there likely isn't room for Bregman.