Jeremy Peña is putting together the best season of his career, and it’s time to start asking some serious questions about what comes next.

After a strong rookie campaign and a magical playoff run in 2022, Peña has reemerged as one of the best shortstops in baseball. His numbers are now right in line with, and in some cases better than, Bobby Witt Jr., the player many consider the gold standard at the position. But Peña's resurgence isn't the only headline, he’s now officially signed with Scott Boras, baseball’s most powerful agent, signaling that a major payday could be on the horizon.

That decision raises real questions about Peña’s future in Houston. With just two years left on his deal, is he heading toward the same path as other homegrown stars who have ultimately walked in free agency? Or will the Astros finally reverse course and invest long-term in one of their own? The team’s payroll philosophy, built around letting expensive veterans leave while developing new talent, has worked for years. But Peña’s rise is testing just how far that system can stretch.

As his star continues to rise, the pressure is mounting. Will Houston commit to keeping him, or let another one slip away?

Be sure to watch the video below as ESPN Houston's Paul Gallant weighs in!

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