Jeremy Peña nearly signed an extension with Astros before one key detail ruined it

The Houston Astros had a pair of reminders over the weekend that they may want to prioritize an extension for shortstop Jeremy Peña. Peña's deal to avoid arbitration was a reminder that his price is only going to get higher, and Alex Bregman getting the last laugh one year after walking away from Houston shows that Dana Brown and the front office should act quickly.

It seems that the Astros were on a path toward accomplishing that goal before a familiar foe got involved in the process. The Athletic's (subscription required) Chandler Rome reports that the Astros and Peña were in the final stages of agreeing to a contract extension before Peña decided to switch his representation to Scott Boras. Boras' involvement in the deal derailed the deal, and it remains unclear if the two sides can return to the table.

Astros insider reveals Jeremy Peña tidbit that could kill any hope of an extension

Astros fans are no strangers to the damage that Boras can do with a Houston star. It was Bregman who passed on a long-term deal with the Astros last offseason to sign a creative three-year deal from the Boston Red Sox. Of course, for Bregman, it seems that getting the most money while also having long-term stability was the difference maker.

The Astros offered Bregman a six-year contract, but didn't have the highest AAV or the most overall money in their proposal. It's a steady reminder of what the future may hold for Peña.

Almost as a principle, Boras strongly urges his clients to avoid contract extensions before they reach free agency. There are instances where a team can provide an exception, but Houston likely isn't the first team that comes to mind when doing so. When faced with paying more to keep a player or trading him before he hits free agency, the Kyle Tucker trade already answers that debate for what Houston prefers.

That being said, if there was a time for Houston to buck the trend, it would be now. They have nearly $100 million coming off their books next season, and are even cleaner the offseason after that. That's more than enough flexibility to pay Peña at the top of the market while also leaving themselves flexibility for moves elsewhere.

It's Boras, so that scenario shouldn't be viewed as likely, but that doesn't mean Houston should just give up on something they once believed had to get done.