Jeff Passan hints Red Sox could face unexpected roster upheaval in free agency

Trevor Story has been a revelation for the Red Sox in 2025. Does that mean he's likely to leave in free agency?
Boston Red Sox shortstop Trevor Story celebrates against the Cleveland Guardians.
Boston Red Sox shortstop Trevor Story celebrates against the Cleveland Guardians. | Winslow Townson/GettyImages

Trevor Story has been one of the best stories in baseball this season, regardless of team. What once appeared to be a lost cause and eventual DFA has turned into one of the key pieces of Alex Cora's lineup, and one of the key factors in the Red Sox's postseason chances.

Story began the year struggling badly at the plate, and the walls started closing in throughout May. During that month, the veteran shortstop slashed .158/.200/.232 with a 34.7% strikeout rate, good for a paltry 13 wRC+. By that latter metric, he was 87% worse than the league-average hitter in May.

Luckily, things have turned around, and Story has righted the ship in a big way since the All-Star break. He's slashing .265/.324/.476 in the second half, which comes out to a 114 wRC+, adding nine steals and eight home runs to his season total to enter the fabled 20/20 club.

All that recent success has fans and analysts now asking a shocking question: Will Story opt out of his contract at season's end?

Jeff Passan questions if Red Sox SS Trevor Story will make shocking free agency decision

To this point, it has practically been a guarantee that Story would opt in to the remainder of his contract, which spans two years and is worth $55 million.

However, Jeff Passan of ESPN re-opened the question in his latest offseason preview, acknowledging that Story actually has a decision in front him, even if the answer appears obvious.

"The lack of shortstop depth in the class makes it tempting, but the combination of what Story is owed (two years, $55 million) and his age (33 next year) is too risky to give up, even after a strong comeback season," the ESPN reporter wrote.

Passan did conclude that Story would "probably not" opt out, but it is a testament to the shortstop's turnaround that the word "probably" has to even be thrown into the conversation.

On the year, he's hitting .259/.306/.436 with 23 home runs and 25 steals. If he can hit two more blasts, he'd become the third Red Sox player ever with a 25/25 season, joining Mookie Betts (2016 and 2018) and Jacoby Ellsbury (2011).

If he didn't have a history of injuries and underperformance — this is the first time he's played more than 100 games in a season since signing with Boston, and he's never posted a wRC+ above 103 with the Red Sox — the opt-out conversation would probably be a bit trickier to navigate.

Still, this version of Story is more than worth the remainder of his contract. If he does opt in, Red Sox fans should be excited to see what he can bring to the table in 2026 and 2027.