The Astros don’t want to repeat the missteps of the past, especially the one that cost them Alex Bregman. This time, with Jeremy Pena emerging as a cornerstone of their future, the front office isn’t wasting a moment. The urgency was quite noticeable the moment word got out that Pena had aligned himself with powerhouse agent Scott Boras. That development sent a clear message across the league: Pena is preparing for a big payday. But the Astros? Well, they’re just as ready to fight for him.
This year is going great for Pena. He’s setting personal bests across the board, hitting .322, with a .378 OBP, a .489 slugging percentage, and an .867 OPS, all career highs. Locking him up long-term would be a major win for the Astros.
Quite naturally, the team’s GM, Dana Brown, dialed Boras, signaling the organization’s intent to go all in on retaining their star shortstop. Afterwards, Brown even pulled back the curtain on what exactly was discussed between him and Boras.
“Astros GM Dana Brown told the team’s pregame radio show that he called Scott Boras right away after Jeremy Pena hired Boras as his agent. Brown said he told Boras that we’re still interested in signing Jeremy long-term and we’ll be in touch,” MLB insider Chandler Rome revealed on X.
Astros GM Dana Brown told the team’s pregame radio show that he called Scott Boras “right away” after Jeremy Peña hired Boras as his agent. Brown said he told Boras that “we’re still interested in signing Jeremy long-term and we’ll be in touch.”
— Chandler Rome (@Chandler_Rome) June 29, 2025
Yep, the Astros have long been hailed as one of baseball’s model franchises. But there’s a persistent critique surrounding their track record with retaining key players. Over the past several years, the front office has allowed multiple franchise cornerstones to walk in free agency, drawing mixed reactions from fans and analysts.
Last offseason, they let go of Bregman, Kyle Tucker, and Ryan Pressly, and the fans weren’t entirely happy about it. Now, losing Pena would draw further backlash, which the management wouldn’t want.
Pena parting ways with his old agent and joining hands with Boras drew a bit of criticism from the ex-Marlins president, David Samson. However, the move is understandable. He is looking for a much bigger payday, and who better than Boras to get him the best deal possible?
But considering the Astros’ willingness to retain Pena, the drama might not last long.
A record-breaking deal might be in the making for Jeremy Pena
Currently, Jose Altuve is the highest-paid player on the Astros’ roster, with a 5-year $125 million deal with the team. Now, if the speculations are anything to go by, Jeremy Pena would make a new record in Houston.
Reportedly, the Astros were looking to close in on a $100 million deal with Pena. But Scott Boras’ entry might change the entire scenario now. As reported by Sporting News, one teammate of Pena suggested he deserves $300 million. That might sound like a stretch, but Pena’s performances are making a strong case. So, how much would be enough for the Astros to retain Pena?
Well, as of 2025, there are eleven shortstops with deals worth over $100 million. And guess what, Pena is outperforming all of them in WAR this season! However, it’s still highly unlikely that he will land one of those massive $300 million deals.
For some perspective, Willy Adames landed a 7-year, $182 million deal with the Giants last December. And he’s been pretty average compared to what Pena’s doing right now. One would think anything above and around $200 million would be a justified amount for Pena.
However, as Boras is now in the scene, expect the unexpected and a record-breaking money-roll in the history of the Astros.
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