Largest Free Agent Contracts in MLB History: Shohei Ohtani Aiming for Record $600 Million Deal

Largest Free Agent Contracts in MLB History: Shohei Ohtani Aiming for Record $600 Million Deal

Joel Reyes
updated at December 5, 2023 at 2:02 AM
In this article:
Lionel Messi logo
Inter Miami CF logoFArgentina logo
  • Shohei Ohtani is expected to sign the largest free-agent contract in MLB history
  • Aaron Judge holds the current record, signing a $360 million contract with the Yankees
  • Bryce Harper held the previous record, signing a $330 million deal with the Phillies

The 2023 MLB Winter Meetings have officially begun.

All eyes are on Japanese superstar Shohei Ohtani, who is expected to sign a contract close to $600 million this offseason.

Sports Brief looks at the largest free agent contracts in MLB history, with the Ohtani sweepstakes heating up.

Shohei Ohtani, Aaron Judge, Bryce Harper, Gerrit Cole, MLB
Shohei Ohtani celebrates after hitting a home run for the Angels. Image: Scott Winters.
Source: Getty Images

MLB's largest free agent contracts

1. Aaron Judge (Yankees, $360 million)

Judge decided to test free agency after declining the Bronx Bombers’ $213.5 million extension offer shortly before Opening Day of the 2022 MLB season.

That decision paid dividends for Judge, who produced a season for the ages in his free-agent walk year.

He smashed the American League home run record last year, hitting 62 dingers.

The Yankees and the San Francisco Giants had a bidding war for Judge’s services, with the 6-foot-7 outfielder ultimately deciding to sign a nine-year, $360 million deal to remain in New York, per ESPN.

2. Bryce Harper (Phillies, $330 million)

Harper decided to move to the City of Brotherly Love in 2019, signing a 13-year, $330 million deal with the Philadelphia Phillies, per CBS Sports.

He had to wait until the second week of Spring Training games before signing at the time, the biggest free-agent contract in the history of the four major professional sports in North America.

The contract has proven to be a steal for the Phillies, given the large amounts of money being spent on superstar free agents recently.

Harper has lived up to his contract thus far, winning his second career National League Most Valuable Player Award in 2021 and leading the Phillies to a World Series berth in 2022. He won the NLCS MVP award that same year.

3. Corey Seager (Rangers, $325 million)

Seager decided to leave the Los Angeles Dodgers in 2021, signing a mammoth 10-year, $325 million deal with the Texas Rangers in free agency.

That has proven to be money well spent for the Rangers, who won the World Series this year thanks to Seager.

He was named the 2023 World Series MVP after hitting three homers over five games against the Arizona Diamondbacks.

He became just the fourth player in MLB history to win two World Series MVP awards, joining Sandy Koufax, Bob Gibson, and Reggie Jackson on the exclusive list.

4. Gerrit Cole (Yankees, $324 million)

The Yankees bolstered their pitching staff in a big way in 2019, signing Cole to a monster nine-year, $324 million deal to be their ace.

It remains the largest free-agent contract for a pitcher in MLB history.

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Ohtani and Messi's marketability

Sports Brief recently reported on an MLB exec comparing Ohtani to Lionel Messi in terms of their marketability.

Messi helped transform the fortunes of Inter Miami when he joined the MLS club last June.

Ohtani is expected to do the same for his future team, providing a boost to their ticket sales, merchandise sales, and TV ratings.

Joel Reyes photo
Joel Reyes
Joel Reyes is a sports editor at with a Bachelor of Arts degree in Journalism from the University of the Philippines. He has eight years of work experience in sports writing.