With 22 games to go, our Boston Red Sox maintain a record of 78-62. They are 2.5 games back of the Toronto Blue Jays for the American League East lead. They sit tied atop the Wild Card race with the New York Yankees, up 4.5 games on the third-place Seattle Mariners and up 6 games on a playoff spot. At this point, it would take a pretty disastrous collapse for the team not to at least make a postseason appearance.
So, ever the man to live in the moment, I wanted to take a peek at what Craig Breslow
and company will be tasked with this winter to turn this successful season into a run of multiple successful seasons.
The Red Sox’ offseason will begin with two very big decisions, but not by the team. The elder statesmen of the team’s offense, Alex Bregman and Trevor Story, both have opt-outs in their contracts. While both players are in their early thirties and man the left side of the team’s infield, their contract situations — and the effect on the team at large — could not be more different.
Bregman is in the first year of a three-year/$120 million deal with an opt-out after each of the first two seasons. Aside from having his best offensive season since 2019, Bregman has become an invaluable leader in the clubhouse and offered loads of stability in a season without much. On top of that, the Red Sox do not have any sort of internal successor at third base. If and when he opts-out, I firmly believe a long-term deal will be reached with the third baseman to keep him in Boston for the rest of his career.
Trevor Story’s situation is a bit more complicated. In the fourth year of a six-year/$140 million contract, Story has finally had his coming out party in Boston. After a middling 2022 and a disastrous 2023 and 2024, Story has been a revelation in 2025. He has been worth 3.0 fWAR in 136 games and is leading the team with 88 RBIs. The pair of him and Bregman have been offered the incredibly young team a sort of north star to aspire to. All that being said, Trevor only needs to beat $50 million if he elects to opt-out. As he continues his revenge tour, it is becoming harder and harder to see some team not offering him that.
Where Story’s deal gets complicated is the Red Sox’ option to opt-in and tack on a seventh year to the deal if Story opts-out. Now, initially I scoffed at this idea. Paying a 35-year-old Trevor Story $25 million seems ill-advised. And it probably is! But… I might do it?
Marcelo Mayer is the obvious heir to the Red Sox shortstop job. But his concerning injury history and relative underperformance with the bat in his MLB stint this year (small sample size, I know) does give one pause in regards to simply handing him the keys next season. If Story walks and Mayer disappoints next season, the Red Sox will simply be out of a shortstop. It’s a dangerous path to go down.
In a perfect world, Story simply opts-in and plays out the last two years of his deal. He likely moves over to second base at some point while Mayer takes over short. But we don’t live in a perfect world, and the headache that third year might cause may just be worth it in the end. Whatever happens, the Alex Bregman and Trevor Story experience has been a blast to watch in 2025. I can only hope it continues next year.
