Biggest contracts in MLB history: Where Vladimir Guerrero Jr. ranks as newest member of $500 million club

Vladimir Guerrero Jr. became the third member of MLB’s $500 million contract club when he signed a 14-year extension for that exact figure with the Toronto Blue Jays on Sunday night. It’s the latest in a string of record-breaking deals baseball has seen in recent years. Guerrero’s pact is the largest contract extension ever signed, and he beat Mike Trout’s previous mark of $426.5 million.

The deal comes two weeks into the 2025 MLB regular season and four months after Juan Soto broke records in free agency. Soto signed a 15-year, $765 million contract with the New York Mets in December. That deal broke a record set by two-way superstar Shohei Ohtani a year earlier.

With MLB’s Biggest Contract Ever Leaderboard in consistent flux over the last few years, you might be wondering: What are the most lucrative deals in the sport’s history?

Well fancy that, below you’ll find the answer to that particular question. We’ve sorted by total guaranteed salary without any adjustments made for deferrals. That’s why, as you’re about to see, Dodgers two-way superstar Shohei Ohtani comes in at his $700 million despite the fact that his salary obligations are heavily, heavily deferred into the distant future, thus significantly lowering the present-day value of his contract.

To the (very high) numbers … 

Biggest contracts in MLB history

(List based on total money)

1. Juan Soto, New York Mets: 15 years, $765 million (free agent) 
2. Shohei Ohtani, Los Angeles Dodgers: 10 years, $700 million (free agent)
3. Vladimir Guerrero Jr., Toronto Blue Jays: 14 years, $500 million (extension)
4. Mike Trout, Los Angeles Angels: 12 years, $426.5 million (extension)
5. Mookie Betts, Los Angeles Dodgers: 12 years, $365 million (extension) 
6. Aaron Judge, New York Yankees: Nine years, $360 million (free agent)
7. Manny Machado, San Diego Padres: 11 years, $350 million (extension)
8. Francisco Lindor, New York Mets: 10 years, $341 million (extension)
9. Fernando Tatis Jr., San Diego Padres: 14 years, $340 million (extension)
10. Bryce Harper, Philadelphia Phillies: 13 years, $330 million (free agent)

Ohtani set the record (and then some), but barley held it for a year. Now Soto holds that honor, a $765 million pact with the Mets the likes of which MLB has never seen before. Is this the new normal, record-setting contracts or extensions every year? Probably not. But suffice to say, there’s plenty of money to go around.