In December 2013, Jacoby Ellsbury arrived in the Bronx with one of the richest contracts ever handed to a center fielder: seven years, $153 million guaranteed. The Yankees were betting on a fast, versatile outfielder who could contribute on both sides of the ball for the better part of a decade. Instead, the deal turned into one of the most debated contracts of the modern era.
The Contract Breakdown
- Team: New York Yankees
- Signed: December 7, 2013
- Length: 7 years (2014–2020)
- Total guaranteed value: $153 million
- Average annual value: $21.9 million
The deal was structured as a straightforward, fully guaranteed commitment — no opt-outs, no notable performance bonuses, just a consistent annual salary for seven years. That kind of structure works when the player stays healthy and productive. Ellsbury was neither for most of the contract’s run.
The Fine Print That Led to a Legal Fight
In MLB, a fully guaranteed contract means the team owes every dollar regardless of injuries, performance, or roster changes. Ellsbury had exactly that protection. But it didn’t prevent a fight: the Yankees attempted to withhold approximately $26 million, claiming the outfielder had undergone unauthorized medical treatments. The MLB Players Association filed a grievance in December 2019, and the dispute was ultimately settled out of court in April 2022.
Where This Contract Stands Historically
Despite its size, Ellsbury’s deal doesn’t crack the top tier of the biggest contracts in MLB history. Its legacy isn’t about prestige — it’s about how quickly a fully guaranteed, long-term investment can unravel when a player can’t stay on the field.
How He Got Here
Before joining the Yankees, Ellsbury hadn’t signed any significant multi-year deals. The 2013 agreement was a career-defining leap — and ultimately a career-defining burden. Over his entire MLB career, he collected $148 million in salary earnings (base salary, signing bonuses, and earned bonuses — not including endorsements or any play outside the U.S.).
Why This Contract Is Still Talked About
Ellsbury played in just four of the seven seasons covered by the deal (2014–2017). He didn’t appear in a single MLB game in either 2018 or 2019 due to recurring injuries. The Yankees released him in November 2019 with roughly $26 million still owed and tried to avoid paying it — a battle that ended with a private settlement in 2022. It’s the kind of contract story that front offices still reference when weighing the risks of long-term, no-escape deals for players on the wrong side of 30.
