The 20 biggest MLB contracts for pitchers with Tarik Skubal set to shatter record - USA Today

Back-to-back Cy Young winner Tarik Skubal is a free agent this winter and will likely fetch the richest contract for a pitcher in Major League Baseball history, a mark currently held by the Los Angeles Dodgers' $325 million pact with Yoshinobu Yamamoto.

Skubal, who turns 30 on Nov. 20, won the 2024 and 2025 AL Cy Young Awards with the Detroit Tigers and was traded to the Dodgers this summer with the Tigers anticipating they wouldn't be able to afford their homegrown lefty come winter.

Yamamoto's 12-year deal with the Dodgers upon his arrival from Japan broke the record set by Gerrit Cole, who agreed to a nine-year, $324 million contract with the New York Yankees prior to the 2020 season. Cole's deal was signed just days after Stephen Strasburg's $245 million contract temporarily was the largest in baseball history.

The biggest contract for a left-handed pitcher belongs to the New York Yankees' Max Fried, who signed an eight-year deal with the Yankees after the 2024 season.

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