10 biggest contracts handed out in the history of MLB free agency

Bryce Harper was always destined for a monster free agent contract. Photo from NYT.

The biggest MLB free agent contracts ever involve serious dollar amounts.

The collective bargaining agreement in MLB is the strongest in American sports and contracts in the league are fully guaranteed. This means that players see every one of these dollars unless there is a buyout or renegotiation somewhere down the line. These are not inflated like NFL contracts where the final years of a contract are rarely seen because of salary cap limitations. These are simply massive contracts that are among the biggest in sports history.

Biggest MLB free agent contracts ever

One of the reasons that baseball contracts have such eyewatering values is their length. Unlike football contracts which tend to be for four or five years, the top baseball deals lock a player in for seven to ten (or more) seasons.

Baseball players can produce at a higher level for longer than other sports because the wear on the body is different. This is especially true for position players (except catchers) though when the decline comes, it comes fast. Here is a look at the ten largest MLB free agency contracts of all time.

Albert Pujols, Angels – 10 years, 240 million

Albert Pujols signed a contract with the Anaheim Angels in 2012 that tied him to the franchise for 10 seasons. His previous 11 years with the St. Louis Cardinals saw him win a pair of World Series titles and the MVP three times in 2005, 2008, and 2009.

The problem was that the contract was signed when Pujols was already 32 years old and injuries (along with age) meant that Pujols was overpaid for his time in the American League.

What stops Pujols from being one of the biggest MLB free agent busts is that he was able to put up 1,180 hits and 222 home runs on the West Coast.

Anthony Rendon, Angels – 7 years, $245 million

Anthony Rendon hit the free-agent market in a year he was considered to be the best position player available. Selected sixth overall in the 2011 MLB Draft by the Washington Nationals, Rendon was an All-Star and World Series Champion with the team in his contract year.

That parlayed into Rendon signing a megadeal with the Los Angeles Angels that pays $35 million per season, the highest annually for a third baseman.

Stephen Strasburg, Nationals – 7 years, $245 million

Sometimes taking a gamble pays off. Stephen Strasburg still had $100 million left on his initial deal with the Washington Nationals when he opted out of the final four years of that contract. It was the correct decision for the player, with the right-handed pitcher putting up a 3.32 ERA while leading the National League in wins (18) in his contract year.

He also won the World Series MVP, but as of 2021, he looks like one of the worst free agent busts as he has made just seven starts with an awful 5.74 ERA through the first two seasons of his megadeal.

Alex Rodriguez, Rangers – 10 years, $252 million

This was the first megadeal in the history of baseball and ushered in a new era of free-agent spending. The biggest deal before this was signed days earlier when Mike Hampton agreed to a head-turning $121 million deal with the Colorado Rockies.

That the A-Rod deal would so thoroughly blow that one out of the water sent shockwaves throughout the sports world. The contract took a 25-year-old Rodriguez with his entire future in front of him to Texas. He only played three years of the deal before being traded to the New York Yankees.

This wasn’t because the deal was a bust, however, with A-Rod winning the American League MVP in 2003 and averaging 52 home runs and 132 RBIs over those three seasons.

Alex Rodriguez, Yankees – 10 years, $275 million

To be on a list like this twice is almost hard to believe. That is where Rodriguez finds himself however after he opted out of the final three years of his initial monster deal.

He had already won two more MVP Awards with the Yankees in 2005 and 2007 and everything (other than postseason hitting) was in his favor. The timing of his opt-out in the middle of Game 4 of the 2007 World Series was nonsensical, but it led to A-Rod resigning with the Yankees for more money from 2007-17.

The sides made up and were vindicated with the Yankees winning the 2009 World Series.

Manny Machado, Padres – 10 years, $300 million

The way contract values were increasing it was only a matter of time before someone became baseball’s first $300 million player. That someone was third baseman/shortstop Manny Machado when he left the Los Angeles Dodgers, who he had been traded to that July, for the San Diego Padres.

Machado’s contract runs from 2019 to 2028 and after a year of finding his feet in San Diego, he has been a success. After signing one of the largest MLB free agency contracts of all time, Machado finished third in National League MVP voting in 2020 and is considered one of the elite offense/defense players in the league.

Gerrit Cole, Yankees – 9 years, $324 million

Gerrit Cole‘s deal which saw him leave the Pittsburgh Pirates for the New York Yankees was the richest annually ever signed at the time. The contract is also unique as it is the second-longest ever given to a pitcher, a position where burnout and injury can ruin a career in an instant.

The only longer deal was signed by Wayne Garland in the 1970s and the two contracts do not compare.

Cole has been a success so far with the Yankees. He has 337 strikeouts and a 3.11 ERA with the New York franchise through two seasons, though he will need to rebound from a poor showing in the 2021 Wild Card Game against the Boston Red Sox.

Max Scherzer, Mets – 3 years, $130 million

This deal needs to be on the list even though it is not close to the rest in overall value.

At 37-years-old, Max Scherzer became the oldest player to sign a $100 million deal with his contract from 2022-24 with the New York Mets.

The deal is the largest by annual salary in the history of the sport, paying the pitcher $43.33 million per season.

Scherzer even has an option to opt-out after the second year of the deal should he not want to earn such crazy money the year he turns 40. Scherzer is a three-time Cy Young award winner who even at 36-years-old was getting the job done. He went 15-4 with a 2.46 ERA the year before this monster deal was signed.

Corey Seager, Rangers – 10 years, $325 million

The second of the biggest MLB free agent contracts ever was signed in the 2021-22 by Corey Seager when he put pen to paper on a deal with the Texas Rangers.

The 27-year-old was the National League Rookie of the Year with the Los Angeles Dodgers in 2016 before starring in their 2020 World Series run.

Seager was named both NLCS and World Series MVP that year as he powered the Dodgers to the championship. They may not have had the same success as a team in 2021, but Seager’s slash line of .306/.394/.521 was as impressive as they come. Seager had interest from teams like the New York Yankees and Toronto Blue Jays before deciding his future was in Dallas.

Bryce Harper, Phillies – 13 years, $330 million

Bryce Harper‘s insane deal that he struck with the Philadelphia Phillies contracted the star to the franchise for parts of three decades.

Running from 2019 all the way to 2031, the right fielder left the Washington Nationals to join the Phillies after seven highly successful seasons in the nation’s capital. A former National League Rookie of the Year, Harper went on to win the NL MVP with the Nationals in 2015.

Signing the biggest contract ever by a free agent (Mike Trout‘s deal with the Los Angeles Angels was a contract extension) hasn’t weighed on Harper as he slugged his way to a second MVP award at the end of the 2021 season. At 29 years old, Harper is in the prime of his career and he should continue to be one of the best players in the game well into the 2020s.