DEAL DONE: Milwaukee has finalized a major agreement, signing a five-year contract valued at $300 million with a new addition to their team….

Largest Contract Extensions in MLB History

To prevent key players from entering free agency, teams often sign them to contract extensions beforehand. The Phillies did this with ace pitcher Zack Wheeler, agreeing to a three-year, $126 million extension through 2027. Wheeler’s initial five-year, $118 million contract with Philadelphia would have expired at the end of the 2024 season, making him eligible for free agency next offseason. Wheeler’s new deal, at $42 million annually, is the highest average annual value for an extension in MLB history.

While Wheeler’s contract has the highest annual salary, Mookie Betts’ $365 million extension with the Dodgers is the largest in terms of new guaranteed total money added to an existing contract.

Here are the largest contract extensions in Major League history, listed in descending order of total dollars:

1. **Mookie Betts, Dodgers** — 12 years, $365 million
Signed in 2020, runs through 2032
Betts was traded from the Red Sox to the Dodgers in 2019. Expected to test free agency after 2020, he instead signed a massive extension with the Dodgers. Betts was runner-up for the 2020 NL MVP Award and helped lead the Dodgers to a World Series championship.

2. **Mike Trout, Angels** — 10 years, $360 million
Signed in 2019, runs through 2030
This extension added to Trout’s remaining two years and $66.5 million, making his new deal worth $426.5 million, the richest in North American professional sports history at the time. Trout rewarded the Angels by hitting a career-high 45 home runs and winning his third league MVP Award in 2019.

3. Manny Machado, Padres– 11 years, $350 million
Signed in 2023, runs through 2033
Originally joining the Padres on a 10-year, $300 million contract in 2019, Machado had the option to opt-out after 2023 but chose to stay with the Padres under this new 11-year contract.

4. **Francisco Lindor, Mets** — 10 years, $341 million
Signed in 2021, runs through 2031
After being traded from Cleveland, Lindor signed the richest ever extension for a shortstop, starting in 2022.

For a list of the longest contracts, including free agent deals, click here.