The Houston Astros are cruising on the field. But off the field, they might just have run into their biggest opponent yet. And no, it’s not the Rangers nor the Yankees. Try Scott Boras—yes, the super agent in MLB. The same guy who helped Juan Soto clinch the massive $765 million deal.

Well, shortstop of the Astros, Jeremy Peña, is in the middle of having a career year. He is crushing the baseball, flashing Gold Glove defense, and climbing the AL MVP ladder. So naturally, you’d think that Houston would want to lock him up for the long term, right?

It turns out that the talks were happening, and the numbers to lock him down long-term were floating around. A $100 million extension for five years looked like it was on the cards. But then the plot twist no one saw coming—Peña changed agents. He shifted to none other than Boras!

According to Chron and other outlets, the extension talks are now paused. Peña is expected to test free agency once his current deal ends in 2027. But now with Boras by his side, it usually means it’s top dollar or bust for the team. And it’s honestly a tough pill to swallow for Houston Astros fans, because it’s not the first time Boras has taken the reins over their superstar player. Astros fans have seen this move before with Carlos Correa and Alex Bregman. The team develops a star, wins with him, and then watches from the back foot as he walks to another team. And though Boras has worked on multiple extensions in Houston, like those for Jose Altuve or Lance McCullers, those are exceptions. And honestly, for fans, the Bregman is still too fresh.

The timing could not be worse. Peña is breaking out offensively this season with a .326 batting average, a .380 OBP, and a .493 slugging percentage. His 144 OPS+ puts him well above the league average, and he already has a 4.5 WAR. This is the third best in the AL; he is just behind Aaron Judge and Cal Raleigh. So maybe, just maybe, given the stats above, the $100 million might not cut it anymore. As Fat Joe said, “Yesterday’s price is not today’s price.”

One can’t forget Peña is just 27 years old and now has Boras on the negotiation table. Soto didn’t end up going to the Mets, not with a mere hundred-dollar difference from the Yankees’ offer; the Mets had a lot to offer. So Peña could be getting ready for a megadeal, too. But that’s just one long-term storyline for the Astros. Right now, they have more business at hand—the trade deadline.

Are the Houston Astros quietly plotting ahead of the deadline?

Now, while the Houston Astros have surged in the standings and it looks like a playoff run is on the cards, their roster still has gaps. Starting pitching is a need, and the front office knows it. And sure, Spencer Arrighetti, Cristian Javier, and Luis Garcia are on track to return later this season, but no one knows how sharp those arms are, right? Not after such an extended layoff. So having a stable piece would offer them peace of mind in October. Now, the even more pressing issue is the hole left by Yordan Alvarez!

With no return date set, Houston’s left-handed power has disappeared. The only switch-hitter is Victor Caratini, and with Jacob Melton also sidelined, the depth is looking thin. So this is where Andrew Benintendi enters the picture.

The Chicago White Sox outfielder is having a bounce-back year. He is hitting .239 and has eight home runs and 29 RBIs. But the most important thing is that he has experience and is available. The Athletic mentions the Sox are open to eating a portion of Benintendi’s very heavy contract. He is owed $17.1 million this year and $15.1 million in 2027. But really, for a franchise that is cautious with big payrolls, this seems like a big deal.

Still, it’s not a sure thing, but if the price and payroll are low, then maybe Houston will pull the trigger. And if Benintendi helps patch the Yordan-sized hole in the lineup, he may be worth the risk. What do you think?