The 5 Biggest Contracts In MLB History

Vladimir Guerrero Jr. struck a deal with the Blue Jays on Sunday evening that will likely keep him in Toronto for the rest of his career. The two sides made history in the process, too, as the contract that the first baseman signed was the third-largest in MLB history.

The negotiations have been lingering for some time. There was some speculation that the deal would get done this past off-season, as the 26-year-old was set to hit free agency this coming winter, but there was no agreement made before Opening Day. But just over a week into the season, it was announced that Guerrero Jr. had signed a deal worth $500 million, which will be paid out over the next fourteen seasons.

The 5 Richest Contracts In MLB History

Where does it rank amongst his peers who are making top dollar? We take a look at the five biggest contracts in MLB history in terms of overall value:

1. Juan Soto – New York Mets (15 years, $765 million)

Soto was the premiere free agent this past off-season, and there were a handful of teams in the running to sign the 26-year-old, who is already a four-time All-Star. He was coming off of a season in which he helped lead the Yankees to the World Series, who were hoping that he would remain in pinstripes for the foreseeable future.

Soto indeed remained in New York, but instead opted to sign with the Mets, who gave him an offer he couldn’t refuse. The outfielder will make $51 million per season for the next 15 years, and the $765 million total value was $65 million higher than any other contract in MLB history.

2. Shohei Ohtani – Los Angeles Dodgers (10 years, $700 million)

When Ohtani signed his deal with the Los Angeles Dodgers ahead of the 2024 season, he shattered all kinds of records. Not only was the $700 million roughly $275 million more than the next-richest ever, but it was set to be paid out over just 10 years. That meant that Ohtani would receive an annual value of an incredible $70 million, which blows the rest of the competition out of the water.

3. Vladimir Guerrero – Toronto Blue Jays (14 years, $500 million)

While he now has the third-largest overall deal in baseball history, the annual value barely keeps him in the top-10. The $35.7 million annually currently tanks Guerrero somewhere between Gerrit Cole and Mike Trout when it comes to the highest yearly wages, who ranked 8th and 9th on that list before Sunday’s signing.

Unlike Ohtani’s deal, Guerrero’s doesn’t include any deferred money. He was also granted a no-trade clause as a part of the deal.

4. Mike Trout – Los Angeles Angels (12 years, $426.5 million)

When he signed his extension prior to the 2019 MLB season, Mike Trout became the highest-paid athlete in North American sports history. It was well deserved, as he was already a three-time MVP at the age of 27, and was widely regarded as the best player in baseball for at least a half decade leading up. His numbers declined a bit as he entered his 30s, and has been dealing with injury issues during the last few seasons. In fact, since the 2020 campaign, Trout has played more than 82 games in a season just once.

5. Mookie Betts – Los Angeles Dodgers (12 years, $365 million)

Mookie Betts signed an extension upon being traded to the Dodgers in 2020, which at the time was the third-richest in North American sports. But it still ranks as the 5th largest deal in MLB history even after the Guerrero extension, but puts him in 18th place when it comes to annual value. Los Angeles has certainly reaped the benefits, as Betts has continued to play at an All-Star level, and they’ve already won two World Series titles with him in the fold.