Why the Trevor Story $55 Million Opt-In May Not Be Guaranteed
The Boston Red Sox find themselves at a pivotal juncture regarding Trevor Story’s future. While it may seem logical that Story will simply play out the remaining two years and roughly $55 million on his contract, the reality is far more complicated. Here are the key reasons why that remaining guarantee may not be as secure as it appears.
1. The Opt-Out Dynamic
Story’s deal included a player opt-out after the 2025 season, meaning he has the choice to walk away from those final two guaranteed years. (SI)
From the Red Sox side, while the team appears “cautiously optimistic” that Story will stay, there’s no formal decision yet. (SI)
Thus: the guarantee exists only if Story opts in. If he opts out, that $55 million becomes moot.
2. Market Value Uncertainty
Story had an excellent 2025 season: healthy, full-time, productive—25 home runs, 96 RBIs, 31 stolen bases. (athlonsports.com)
But prior to that, the first three years in Boston were marred by injuries and diminished performance. (BoSox Injection)
Given his age (turning 33 in November) and history, the open-market value for him may not exceed what he’d earn by staying. One insider called opting out at this point “a financial blunder.” (SI)
So Story and his camp must weigh risk vs reward: bank the sure $55 million now, or gamble for more in free agency with less guaranteed.
3. The Red Sox’s “Escape Hatch”
Interestingly, the club possesses a mechanism to blunt Story’s opt-out: if he chooses to leave, Boston can exercise a seventh-year club option worth ~$25 million for 2028. (bostonsports.today)
In effect, this gives Boston bargaining leverage: either Story opts in for two years, or the team triggers the extra year and still retains him under contract.
That diminishes the leverage Story might have in negotiations, reducing his incentive to risk opting out.
4. Team Strategy & Roster Considerations
From Boston’s perspective, locking in Story for the next two years (or three, if option exercised) provides stability on the left side of the infield. (SI)
Yet, financially speaking, $55 million is a non-trivial commitment for a player whose defensive value has come under scrutiny. Some analysts believe the club might prefer to explore younger, cheaper alternatives rather than commit long-term to a veteran. (BoSox Injection)
If the team were less invested in his long-term presence, they may not push hard for the opt-in, creating additional uncertainty around that guarantee.
5. The Timing Factor
Story must declare his decision within five days after the World Series ends. (SI)
Until that deadline passes, nothing is set in stone. This limbo gives both sides some flexibility — and risk. For Story: he must decide whether to opt in or test the market. For Boston: they must prepare for either scenario.
What this means: the “guaranteed” $55 million is contingent, not absolute — the decision hasn’t yet been made.
In summary
While it appears simple — Story opts in, earns $55 million over two years — the reality is layered:
- He can opt out and test free agency.
- His market value may not exceed what he already has guaranteed, given age/injuries.
- The Red Sox hold an option that weakens his leverage.
- Team strategy and roster dynamics may push either side toward a pivot.
- The decision is still pending, so “guaranteed” remains a bit of a misnomer.
For Boston fans, it’s a reminder: contracts are rarely as straightforward as they read. We’ll have clarity soon — once Story signals his choice.
If you like, I can pull up a breakdown year-by-year of his contract and what opting in vs opting out means financially.
