Baseball has a long and storied history as America's pastime, with players captivating fans for over a century with their athletic feats on the field. While the game itself hasn't changed much, the business side of baseball certainly has. In recent years, salaries and contracts for MLB's biggest superstars have reached astronomical levels, shattering records and redefining just how much teams are willing to shell out to land premier talent.
In this article, we'll take a closer look at some of the most lucrative contracts in Major League Baseball history and break down exactly who has scored the biggest deals in the sport. From decade-long megadeals to record-setting average annual values, we'll examine the money behind MLB's upper echelon.
Overview
To determine who has scored the richest contracts in baseball history, there are two major factors to consider - the total overall dollar amount of the deal and the average annual value (AAV). The overall dollar total represents the grand sum a player will earn over the entire length of their contract. The AAV is determined by dividing the total value by the number of years, showing what a player makes per season on average.
Both metrics are important in gauging contract size, as massive overall sums indicate the incredible investment teams are making, while sky-high AAVs reveal how much annual salary elite superstars can command. When looking at the biggest deals around MLB, the largest totals and highest AAVs help identify the cream of the contract crop.
The largest deals in baseball have traditionally gone to superstar position players - fearsome sluggers and sensational hitters that can single-handedly change the fortunes of a franchise. Mike Trout, Mookie Betts, Manny Machado and Bryce Harper headline position players that have signed deals worth over $300 million. For pitchers, aces like Max Scherzer, Justin Verlander and Gerrit Cole have scored massive $200+ million deals thanks to their mound dominance.
In the past few offseasons, with revenues in baseball soaring, we've seen some eye-popping contracts that have raised the bar yet again. Aaron Judge returned to the Yankees on a $360 million deal, while Manny Machado extended with the Padres for $350 million. Both deals rank near the top in overall value, while Judge's $40 million AAV established a new high water mark for position players, surpassing Mike Trout's previous record.
Let's take a deeper look at who precisely has landed the most lucrative contracts in MLB history, starting with the biggest overall totals.
Largest contracts (total money) in MLB history
Mike Trout, Angels: $426.5 million (2019-30)
The 12-year extension Mike Trout signed prior to the 2019 season absolutely stunned the baseball world. At the time, the $426.5 million total value was the largest deal ever handed out in pro sports history. The contract kept baseball's best all-around player with the Los Angeles Angels for what will likely be the remainder of his incredible career. Trout's massive deal tops this list in overall dollars.
Mookie Betts, Dodgers: $365 million (2021-32)
Prior to the 2021 season, star outfielder Mookie Betts agreed to a huge 12-year, $365 million extension with the Los Angeles Dodgers. Betts' $365 million total trails only Trout for the second-largest deal ever. Still just 30 years old, Betts figures to be among the game's elite players for the duration of this record contract.
Aaron Judge, Yankees: $360 million (2023-31)
After an epic 2022 season, Aaron Judge hit the open market and secured a $360 million, nine-year deal from the New York Yankees. The $40 million average annual value is a new high water mark for position players, and the $360 million total is the third-largest deal in MLB history. Judge spurned more years and higher offers elsewhere to remain in the Bronx.
Manny Machado, Padres: $350 million (2023-33)
Manny Machado joins Judge in reaching a $350 million contract this offseason. He signed an 11-year, $300 million deal with the San Diego Padres prior to 2019, but the team tore that up in favor of a new 10-year, $350 million extension that will make Machado a lifelong Padre. His $350 million total ranks 4th among all MLB player deals.
Francisco Lindor, Mets: $341 million (2022-31)
The New York Mets opened their checkbook in a big way to lock up Francisco Lindor long term, signing him to a 10-year, $341 million extension before the 2022 campaign. Lindor's deal trails only Betts and Lindor for shortstops and ranks 5th among all players in total value.
Fernando Tatis, Padres: $340 million (2021-33)
In February 2021, star shortstop Fernando Tatis Jr. and the Padres stunned baseball by agreeing on a 14-year, $340 million extension. Tatis' $340 million total is the 6th-largest deal ever handed out. While he has yet to play on the extension due to injury and suspension, it signifies the Padres' commitment to make Tatis the face of their franchise.
Rafael Devers, Red Sox: $331 million (2023-34)
After a breakout 2022 season, All-Star third baseman Rafael Devers joined the $300 million club with a new 11-year, $331 million contract with the Boston Red Sox. Devers' extension represents the largest deal in Red Sox franchise history. At just 26, Devers figures to anchor Boston's lineup for the next decade-plus.
Bryce Harper, Phillies: $330 million (2019-31)
Long one of baseball's biggest superstars, Bryce Harper signed a record 13-year, $330 million free agent deal with the Philadelphia Phillies prior to 2019. Harper's $330 million deal was the largest in baseball history at the time, and still ranks as the 8th-biggest contract ever handed out.
Giancarlo Stanton, Marlins/Yankees: $325 million (2015-27)
In 2014, slugger Giancarlo Stanton inked a groundbreaking 13-year, $325 million extension with the Miami Marlins. After being traded to the Yankees, Stanton is still working off this massive contract, which ranks as the 9th-largest in MLB history. When he signed it, Stanton's $325 million deal was the biggest in the sport.
Corey Seager, Rangers: $325 million (2022-31)
Before the 2022 season, the Texas Rangers made a huge free agent splash by signing star shortstop Corey Seager to a massive 10-year, $325 million deal. It stands as the largest contract Texas has ever handed out and trails only Francisco Lindor's for shortstops. Seager's $325 million total ties Stanton's for the 9th-richest contract.
In addition to these colossal totals, MLB stars are also getting record-shattering average annual salaries. Let's look at the deals with the highest AAV figures in baseball history.
Highest average annual value (AAV) in MLB history
Max Scherzer, Mets: $43.33 million (2022-24)
Future Hall of Fame pitcher Max Scherzer raised the bar for AAV in MLB when he signed a three-year, $130 million deal with the New York Mets prior to 2022. Scherzer's $43.33 million AAV surpassed previous record-holder Mike Trout. He trails only co-teammate Justin Verlander for the highest AAV ever.
Justin Verlander, Mets: $43.33 million (2023-24)
In an incredible turn of events, the Mets followed up their Scherzer signing by inking Justin Verlander to an identical two-year, $86.67 million contract for 2023-2024. Verlander's $43.33 million AAV matches Scherzer for the highest ever for a pitcher.
Aaron Judge, Yankees: $40 million (2023-31)
On top of landing one of the largest overall contract values, Aaron Judge also scored a record $40 million AAV on his new Yankees deal. That $40 million per year average salary is the most ever for a position player, outdoing Mike Trout's previous high of $35.54 million.
Jacob deGrom, Rangers: $37 million (2023-27)
Legendary pitcher Jacob deGrom left the Mets after the 2022 season to join the Texas Rangers on a five-year, $185 million contract. His $37 million yearly salary trails only Verlander and Scherzer for the 4th-highest AAV ever for an MLB player.
Gerrit Cole, Yankees: $36 million (2020-28)
The Yankees made Gerrit Cole baseball's highest-paid pitcher at the time by signing him to a nine-year, $324 million deal before the 2020 season. Cole's $36 million average annual value remains among the top five marks in MLB history.
The exponential growth of contracts in recent years shows how much teams are willing to invest in elite stars who can elevate their franchises. With salaries and player mobility continuing to escalate, don't be surprised if more staggering contracts get signed in the near future. For now, the players above represent baseball's financial elite when it comes to the biggest deals in the sport's history.
Conclusion
As revenues and payrolls expand around baseball, teams seem more willing than ever to commit to decade-long megadeals for premium superstars who can change a franchise. With other young phenoms like Juan Soto approaching free agency in coming years, it seems likely even bigger contracts could be signed in the future.
For now, the biggest deals belong to a select group of elite players like Trout, Betts, Judge, Machado, and Scherzer. The escalating paydays enjoyed by MLB's highest performers reflect their tremendous on-field impact and star power. But with teams now proven to have nearly bottomless pockets, another superstar could soon come along and land an even more monumental deal, raising the bar yet again.
The massive contracts handed out to baseball's best make it clear: elite talent commands an elite paycheck in today's MLB landscape. Don't be surprised if the record books get rewritten as this economic environment enables franchises to spend more than ever before to land premier superstars. The sky is truly the limit for the sport's next blockbuster deal.
