In March 2019, the Boston Red Sox locked up Chris Sale for five seasons in one of the biggest pitcher contracts of that era. Sale was in his prime, Boston wanted to stay competitive in the AL East, and the two sides got a deal done before he ever hit free agency. Injuries would later complicate things — but the money was never in question.
His Last Big Contract
- Team: Boston Red Sox
- Signed: March 22, 2019
- Length: 5 years (2020–2024)
- Total Guaranteed: $145 million
- Average Annual Value: $29 million
How the Deal Was Structured
Sale received $145 million fully guaranteed over five years, averaging $29 million per season. The extension was negotiated before he reached free agency, letting Boston retain him without a bidding war. The deal included deferred payments — though the exact breakdown hasn’t been publicly confirmed — and carried no performance clauses. Sale collected every dollar regardless of what happened on the mound.
What «Fully Guaranteed» Actually Means
In MLB, a fully guaranteed contract means the player gets paid in full no matter what — injuries, poor performance, or even a trade don’t change that. Sale collected everything Boston owed him even as injuries limited his appearances, and even after the Red Sox dealt him to Atlanta before the 2024 season.
The deferred portion of the deal — payments made after the contract ends — is standard practice in large MLB agreements. It helps spread out the salary cap impact without reducing what the player ultimately earns.
Where Sale Ranks Among MLB Pitchers
- Rank among highest-paid pitchers in MLB history: #22
Rankings are based on total guaranteed value, not adjusted for deferrals. Data via Spotrac and Baseball-Reference as of August 11, 2026.
At $29 million per year, Sale sits firmly in the elite tier of MLB pitchers — not at the very top, but well inside the conversation. The ranking reflects both his talent and the reality that the market has since pushed several arms past that number.
Earlier Contracts
- Chicago White Sox, 2013–2019: $32.5 million extension
Sale built his market value on the South Side of Chicago, where a $32.5 million extension kept him with the White Sox through 2019. Those were the years he established himself as one of the best starters in the American League — consistent, dominant, and nearly unhittable when locked in.
The jump to Boston represented the full payoff: $145 million for five years. And even though injuries slowed him down in New England, Sale reminded everyone what he’s capable of when healthy — winning the 2024 NL Cy Young Award with the Atlanta Braves.
Career Earnings
Add it all up and Chris Sale has earned $178 million in guaranteed MLB money across his career. That figure covers base salary, signing bonuses, and earned bonuses — not endorsements or any income from outside the United States.
