Red Sox Pitcher Chris Sale Has a Contract Quirk That’ll Keep Him Paid After Retirement

Chris Sale signed a five-year, $145 million contract extension with the Red Sox last year that kicks in this season. He won’t take the field this season after undergoing Tommy John surgery at the end of March, but the Red Sox are still going to have to pay him his salary this season.

And the Red Sox better get used to paying Sale when he’s not playing with them because they’ll be paying the ace long after he retires. As a way to save money now, the Red Sox put a lot of deferred money in Sale’s contract, which means they’ll be paying him tens of millions years from now.

Chris Sale’s MLB career so far

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The White Sox drafted Sale out of Florida Gulf Coast University with the 13th overall pick in the 2010 MLB draft. He would go on to play seven seasons for them, going 74-50 with a 3.00 ERA in 228 games, including 148 starts.

He struck out more than 1,200 batters in 1,110 innings. After the 2016 season, the White Sox traded Sale to the Red Sox for a package led by 3B Yoan Moncada and SP Michael Kopech.

In his first three seasons in Boston, Sale is 35-23 in 84 starts with a 3.08 ERA and 763 strikeouts in 519.2 innings. Overall in 10 seasons, he is 109-73 with a 3.03 ERA and 2,007 strikeouts in 1,629.2 innings over 312 appearances, including 232 starts.

Chris Sale’s latest contract with Boston

In the 2017 and 2018 offseasons, Boston exercised separate team options for $12.5 million and $15 million, respectively. Then just before the 2019 season started, Sale got his big payday when the Red Sox gave him the $145 extension effective this year.

The Providence Journal shares details of the extension, which kept his $15 million salary for last season intact. His salary doubles to $30 million for this season, and stays there until 2022, then it drops to $27.5 million each season in 2023 and 2024.

The team has a $20 million team option for 2025, when Sale will be 36. That option becomes guaranteed if Sale is healthy at the end of the 2024 season and finishes that year in the top 10 in Cy Young voting.

Sale’s finishes in Cy Young voting can also bump up his base salaries from 2021-24, with winning the award gives him another $2 million in salary for the following season.

There are other details in Sale’s contract, including one-time bonuses for winning certain season-ending awards, which could also increase the salary in his option year. Sale has an opt-out clause after the 2022 season; if he exercises it, he would become a free agent. And he has a limited no-trade clause, allowing him to block deals to three teams this year, and it becomes a full no-trade clause in the first half of next season, once he reaches 10 years of major league service time.

Paid through 2040

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Each season of the contract includes deferred money that guarantees Chris Sale will continue to get paid for many years to come. Each guaranteed season of the contract includes $10 million in deferred money that is due to Sale on June 30 in the 15th year after it is earned.

So the deferred money for 2024, the last guaranteed year of Sale’s extension, will be paid to him on June 30, 2039. If the Red Sox pick up the 2025 option, $5 million of the $20 million salary will be deferred until June 20, 2040.

Deferred money is common with big-money contracts, with the most famous example of a player getting deferred money is Bobby Bonilla. He retired in 2001, but the Mets continue to pay him more than $1 million annually and will do so through 2035. The payment comes on July 1 every year, and that day has become known as Bobby Bonilla Day around baseball.

-All stats courtesy of Baseball Reference