Done Deal: The Houston Astros and Milwaukee Brewers have officially reached a record-breaking agreement, with the Astros paying $203 million to acquire a six-time All-Pro and three-time Cy Young winning premier pitcher Over Six Year, But…..

The extension chatter at present has primarily centered around three players: Alex Bregman, Kyle Tucker, and Framber Valdez. Brown has been vocal about retaining this trio of star players, but there is also reality to contend with. The odds of retaining all three, while not impossible, are unlikely, to put it mildly. Sooner or later, another star player will leave the Astros. Perhaps more than one. There is a bit of urgency regarding the next potential extension, especially for Bregman, who has only one more season of club control. Tucker and Valdez, however, have two more seasons, so the urgency isn’t necessarily paramount at this very moment. But make no mistake that the pressure is building.

Who could the Astros prioritize in extension negotiations? The easy answer is all three, which is technically correct. After all, Bregman, Tucker, and Valdez have all proven themselves crucial to the entire operation numerous times. Replacing any of them won’t be an easy task. While the farm system isn’t completely devoid of talent, it does lack some high-end talent, at least at the top. It won’t be easy to replace any lost production from those three, at least in the short term. But, again, who takes priority as someone has to?

But there’s not a crystal clear answer. I mean, there isn’t much in terms of public information about the state of negotiations, or lack thereof. A lot of the explanations given lately are more of a generic quality front office quality, such as listening to offers and seeing what the other side says. But receptiveness matters. Of course, each player has different priorities and how the organization views their long-term prospects could differ from the player himself. There’s also the allure of the open market and a player generating the best return they possibly can muster. I am curious, however, about how the Astros proceed as Josh Hader’s contract seems to indicate going all in. Signing Hader was such an interesting change of course from Crane and I can’t help but wonder if even he recognizes something had to adjust on his end about long-term commitments.

At this juncture, I’d speculate that Tucker ought to become the top priority. There is an age component to consider, especially when comparing Bregman and Tucker. Bregman, after all, is entering his age-30 season, although he won’t actually turn 30 for roughly a month. Tucker, however, has just turned 27, so any new contract for him ought to cover more prime years than Bregman. At some point or another, Bregman will enter his decline years while Tucker figures to have at least a few more prime seasons before his decline. Plus, Bregman has appeared to level out around a four-to-five-win player, with some variance in either direction based on his performance since 2022. Replicating his eight-win-plus peak from earlier in his career appears to be an unrealistic target now. While I am a big fan of Bregman’s plate discipline, there is probably more risk in bat than I’d initially suspected, especially if his pull power starts to falter.