And it counted more in earlier seasons - it's adds up to the same amount. This team going to be hanging around the luxury tax every year its in contention at this point so all you're doing is helping one year and hurting a different year. And at this point, you have no idea what the luxury tax even will be 3 years from now - either in the team's needs or with the new CBA - so it's not something you can efficiently plan for.
A player on your team who you must compete with the whole league to keep for another season is a de-facto free agent and has ceased to be an extension candidate.
Mathematically you are correct. But the extension benefits the team regardless. Maybe they have an extra $10-$15M to spend early and $10-$15M less late. But you are still able to get a $30+M per year talent within the CBT because you signed him early. But the AAV is the same regardless of what you actually pay him. You lose some on the front end and gain it on the back end, but you always get more value than the player is actually worth, if he's healthy and performs where you expect. Thats where luck, but also good scouting and systems come in. Bregman had 18.5 bWAR (if you project 2020 to 162g) during his 5/$100M extension. Thats 3.7 WAR per year for $5.4M per WAR. Considering FAs cost at least $8M per WAR it was a great value. If you wait and sign him as a FA most teams can't afford him and/or go over the CBT. Thats the reality of why extensions are more valuable than free agent contracts.
If the Stros are unwilling to give him 5 years honestly that’s pretty ****ing outrageous considering they gave Abreu three. That’s absolutely ridiculous on every plane of existence. I imagine he wants a lot more than that.
You keep saying things matter of factly. The Astros were open to Bregman resigning for $30 million a season, which was $10 million more per year than Walker or Kikcuhi. Kikuchi would also be replacing Valdez's underpaid contract the next year, so not a long term hit. Payroll wise, nothing about his deal was a dealbreaker. Personnel wise, they were complacent and thought a couple of their question marks would pan out. None have, and now you go into next season with Brown being the only reliable starter. You need SP to compete for titles... period.
You say that matter of factly. Walter has absolutely proven himself. He just needs to prove his health. There are still 2 months in the season for Arrighetti, Javier, Garcia, Gusto, Gordon, Alexander, and/or even Blubaugh/Ullola to "pan out" and go into next season as reliable starters. And I still think the Astros get a playoff caliber SP today. He could possibly have control.
