In December 2000, Manny Ramírez put pen to paper on one of the most ambitious contracts in baseball history. The Boston Red Sox locked up the Dominican slugger for 8 years and $160 million fully guaranteed — the second-largest deal ever signed at the time — betting on him as the cornerstone of their franchise heading into the new decade.
The Contract Breakdown
- Team: Boston Red Sox
- Signed: December 12, 2000
- Length: 8 years (2001–2008)
- Total guaranteed value: $160 million
- Average annual value: $20 million
Ramírez was coming off seven dominant seasons in Cleveland and hit the free-agent market at the absolute peak of his powers. Boston’s investment reflected that — and then some.
How the Deal Was Structured
The contract was 100% guaranteed, meaning Ramírez was getting every dollar regardless of injuries or performance. It also included deferred money: a portion of the payments were spread out beyond 2008, with Boston still cutting checks to Manny years after he stopped wearing a Red Sox uniform. That kind of structure was common in the megadeals of that era, letting teams manage the payroll hit over a longer window.
In fact, according to recent reports, Boston’s deferred payments to Ramírez ran all the way through 2026 — nearly two decades after his last game in a Red Sox jersey.
Where He Ranks All-Time
Ramírez sits at No. 20 on the all-time MLB earnings list, based on total guaranteed contract value. Rankings are calculated without discounting deferred money, per Spotrac and Baseball-Reference data as of August 11, 2026.
Before Boston: Cleveland Indians (1994–2000)
- Team: Cleveland Indians
- Seasons: 1994–2000
- Amount: Not publicly disclosed (arbitration)
Manny broke into the big leagues with Cleveland in 1994 and spent seven seasons there, building a reputation as one of the best pure hitters of his generation. The exact figures from his arbitration years were never made public, but those numbers were good enough to make him one of the most coveted free agents on the market when he finally got there.
What He Won — and What He Earned
The Boston years delivered everything the Red Sox hoped for. Ramírez helped end an 86-year championship drought in 2004, was named World Series MVP, and added another ring in 2007. Over his entire MLB career, he collected $244 million in salary — base pay, signing bonuses, and earned bonuses combined, not including endorsements or money earned outside the United States.
Career earnings figures cover MLB salaries only, per Spotrac and Baseball-Reference.
