Baseball history is littered with players whose dreams fizzled before they got their first massive payday, or guys who retired before MLB salaries rocketed into the stratosphere.
But for the lucky few who’ve reached the sport’s pinnacle in recent years, riches awaited.
Let’s examine the 10 biggest MLB contracts of all time, in terms of total dollars rather than average annual value. Note that if a player inked an extension as opposed to a new deal, we only counted the extension money.
We’ll begin with a pair of pacts signed by a controversial former superstar and end with arguably the two best outfielders in the game today.
10. Alex Rodriguez, Texas Rangers, 10 years, $252 million (signed in Dec. 2000)
Alex Rodriguez spent three seasons with the Rangers.
(Jed Jacobsohn/Getty Images)
After the Rangers signed him to a then-record contract prior to the 2001 season, Alex Rodriguez swatted 156 home runs in three seasons and won American League MVP honors in 2003.
Despite that impressive output, Texas traded A-Rod to New York, where he continued putting up superstar numbers and snagged two more MVPs with the Yankees.
9. Alex Rodroguez, New York Yankees, 10 years, $275 million (signed in Dec. 2007)
Alex Rodriguez spent the largest chunk of his career with the Yankees.
(Lisa Blumenfeld/Getty Images)
After winning the MVP in 2007 with the Yanks, A-Rod opted out of his contract and signed another, even-more lucrative one to remain in the Bronx.
He made three more All-Star appearances and helped the Yankees win a title in 2009, but he missed the 2014 season due to a performance-enhancing drug suspension and finished his career under a PED-tainted cloud.
8. Manny Machado, San Diego Padres, 10 years, $300 million (signed in Feb. 2019)
Manny Machado left the Dodgers to join the Padres.
(Sean M. Haffey/Getty Images)
When Manny Machado reached free agency prior to the 2019 season, there was no doubt he’d land a massive payday.
The San Diego Padres ultimately won the bidding war for the superstar infielder, who was entering his age-26 season and had already made four All-Star teams and won a pair of Gold Gloves.
Now, along with another star we’ll meet later on this list, Machado anchors the lineup of an ascendent Friars club.
7. Gerrit Cole, New York Yankees, nine years, $324 million (signed in Dec. 2019)
Gerrit Cole left the Astros to join the Yankees.
(Christian Petersen/Getty Images)
Gerrit Cole led the game in strikeouts (326) and ERA-plus (185) in 2019 with the Houston Astros and finished second in AL Cy Young Award voting.
He then signed a massive contract with the Yankees and proceeded to post a 2.84 ERA with 94 strikeouts in 73 innings in the truncated 2020 season.
Cole remains one of the game’s rare, unequivocal aces entering his age-30 campaign.
6. Giancarlo Stanton, Miami Marlins, 13 years, $325 million (extension signed in Nov. 2014)
Giancarlo Stanton signed a major deal with the Marlins.
(Christian Petersen/Getty Images)
The Miami Marlins locked up Giancarlo Stanton, a generational slugger, to a seismic contract prior to the 2015 season.
Stanton smacked 59 home runs and won a National League MVP award in 2017 before being dealt to the Yankees.
Injuries have limited Stanton thus far in the Bronx, though the 31-year-old still has time to redeem his New York legacy.
5. Bryce Harper, Philadelphia Phillies, 13 years, $330 million (signed in March 2019)
Bryce Harper left the Nationals to sign with the Phillies.
(Mitchell Leff/Getty Images)
As with Machado, Bryce Harper’s free agency was a major event heading into the 2019 season. He was entering his age-26 go-round and already had an NL MVP trophy under his belt.
Ultimately, Harper ditched the Washington Nationals, the club that drafted him, in favor of a lucrative deal with the division-rival Philadelphia Phillies.
The Phils have yet to make the playoffs with Harper on the roster, but he has a chance to change that in 2021.
4. Fernando Tatis Jr., San Diego Padres, 14 years, $340 million (extension signed in Feb. 2021)
Fernando Tatis Jr. signed a megadeal with the Padres.
(Sean M. Haffey/Getty Images)
Fernando Tatis Jr. burst on the scene with a .969 OPS in 84 games during his rookie year in 2019 and followed that up with a .937 OPS and top-four MVP finish in the truncated 2020 season.
That led to a mega-extension from the San Diego Padres, who locked up the preternaturally talented 22-year-old shortstop for what should be the bulk of his big league career.
3. Francisco Lindor, New York Mets, 10 years, $341 million (extension signed in March 2021)
Francisco Lindor signed a major deal with the Mets.
(Mike Stobe/Getty Images)
Francisco Lindor came to Queens this winter via trade from Cleveland. It was part of the New York Mets’ makeover under a new ownership regime led by Steve Cohen.
Lindor was an impending free agent and thus a potential rental, but Cohen and Co. took care of that.
Before he played a regular season game with the Mets, Lindor inked a decade-long extension that should set the market for next season’s rich free-agent shortstop class.
2. Mike Trout, Los Angeles Angels, 10 years, $360 million (extension signed in March 2019)
Mike Trout could spend his whole career with the Angels.
(Sean M. Haffey/Getty Images)
Mike Trout is the best baseball player of his generation. The Los Angeles Angels (the only MLB team he’s ever known) made sure he wouldn’t be able to test free agency.
Just ahead of the 2019 season, the Halos signed Trout to a whopping 10-year extension.
He rewarded the Angels by winning a third career MVP award in ‘19, and it’s probable the 29-year-old will net at least a couple more trophies before he hangs ‘em up.
All that’s left now? Success in the postseason, where Trout has gone a paltry 0-3.
1. Mookie Betts, Los Angeles Dodgers, 12 years, $365 million (extension signed in July 2020)
Mookie Betts was traded from the Red Sox to the Dodgers.
(Tom Pennington/Getty Images)
Mookie Betts didn’t win the NL MVP award in 2020, but he did finish second and guided the Los Angeles Dodgers to their first championship since 1988.
That came after Betts was traded to L.A. from the Boston Red Sox and signed a 12-year extension.
Needless to say, the early returns are positive for the 28-year-old four-time All-Star and the Dodgers after the biggest contract in MLB history.
More From Audacy Sports
- 5 MLB Underachievers Who Are Way Overpaid
- Ranking the 12 Worst Contracts in MLB Ahead of 2021 Season
LISTEN on the Audacy App
Sign Up and Follow Audacy Sports
Facebook | Twitter | Instagram
