Why Red Sox Star's $55 Million Opt-In May Not Be Guaranteed

How will this play out?

Mar 21, 2018; Port Charlotte, FL, USA; A view of a Red Sox baseball bag in the game of the Boston Red Sox against the Tampa Bay Rays at Charlotte Sports Park. Mandatory Credit: Aaron Doster-Imagn Images | Aaron Doster-Imagn Images

Fear not, Boston Red Sox fans. After a month of inaction, there will finally be significant roster moves this week.

"Fear not" might be the wrong phrase to use, though, because there are lots of things up in the air, and it's hard to determine just what Boston should be rooting for. And Trevor Story's intriguing opt-out situation is near the top of that list.

Story isn't in the same situation as Alex Bregman, who has been destined to opt out all along. There would have been almost no argument for him to turn down his two-year, $55 million guarantee entering the season, but leading the team in home runs, RBIs, and stolen bases could change the equation.

Could Story opt out? It's not out of the question

Oct 1, 2025; Bronx, New York, USA; Boston Red Sox shortstop Trevor Story (10) celebrates after hitting a one run home run during the sixth inning against the New York Yankees during game two of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

On Sunday, Chris Cotillo of MassLive reported that although the Red Sox feel somewhat confident about Story's return, there are a couple of other reasons to believe an opt-out is possible, including the representation decision he made four offseasons ago.

"Red Sox executives have been cautiously optimistic that Story, who has two years and $50 million (plus a $5 million buyout) left on his contract, will decide to return. He also hasn’t informed the team of his decision," wrote Cotillo.

"A Story opt-out can’t fully be ruled out because of this winter’s weak shortstop class among free agents (beyond Bo Bichette) and the fact Story switched agencies, from Excel to Wasserman, after signing with the Red Sox in 2022."

Story's six-year, $140 million deal with the Red Sox was viewed by some as a bargain, though it didn't play out that way for the Red Sox in the star's first three years in Boston, all of which were disrupted by injuries.

The question, as ever, is whether Story believes a team out there might be willing to pay more than that $55 million figue to bring him in. And if so, he then must weigh that pay bump against the prospect of leaving this Red Sox squad, for whom he has become a real leader.

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