During the 2018-19 offseason, Bryce Harper became the highest-paid free agent in baseball history, thanks to the $330 million contract he signed with the Phillies. He passed Manny Machado, who was the record-holder for less than two weeks -- the $300 million contract he signed with the Padres had just eclipsed Alex Rodriguez's $275 million megadeal with the Yankees from 2008.
• Photos: Highest paid MLB players
In the 2019-20 offseason, Gerrit Cole and Stephen Strasburg did the same to the free-agent contract mark for pitchers. Strasburg's $245 million deal with the Nationals broke David Price's record $217 million deal with the Red Sox from December 2015. The very next week, Cole signed with the Yankees for $324 million, breaking Strasburg's record. Cole is now the highest-paid free-agent pitcher ever.
Here are all the standard bearers -- the players who have held the title of highest-paid free agent in history, by total contract value -- from Harper to A-Rod all the way back to Pete Rose. This is a progressive list of the single highest-paid MLB free agent over time, going back to the biggest known contracts from the early days of baseball free agency, which began in December 1975.
Note: This list considers free-agent contracts only, and not contract extensions -- such as Mike Trout's all-time record $426.5 million extension with the Angels, or Giancarlo's Stanton $325 million extension signed with the Marlins. It's ranked by the total amount of the contract and not average annual value (AAV), another popular method of ranking contracts. This list also excludes Hall of Fame pitcher Catfish Hunter, who was made a free agent and signed with the Yankees in December 1974 -- a year before the official dawn of free agency -- when his contract with the A's was voided following a salary dispute.
2019: Bryce Harper, Phillies -- 13 years, $330 million
Machado's deal with San Diego set the floor for Harper's asking price, and Stanton's 13-year, $325 million extension with the Marlins (which he is now playing out with the Yankees) also provided parameters for Harper and his agent, Scott Boras. Harper's deal notably did not include any opt-outs, in addition to a full no-trade clause, meaning Harper and the Phillies' fortunes will be wed to each other for more than a decade to come. Already a National League Rookie of the Year, MVP and six-time All-Star when he joined the Phillies, Harper has continued to shine bright in Philadelphia, but the team hasn't reached the postseason in three seasons with the star slugger.
2019: Manny Machado, Padres -- 10 years, $300 million
Machado was knocked off the mantle in less than a month, but he will go down as the first $300 million free agent in MLB history. When Machado inked his deal, no free agent in the history of the four major North American professional sports had ever signed a contract that big. The 26-year-old Machado got his deal coming off a season in which he hit 37 home runs with 107 RBIs, and he was already a four-time All-Star and two-time Gold Glover.
2008: Alex Rodriguez, Yankees -- 10 years, $275 million
Before Machado, A-Rod was the longtime record-holder, most recently under the blockbuster new deal he negotiated with the Yankees before the 2008 season. Rodriguez's $275 million contract broke the record that had previously been held… also by A-Rod, under his first blockbuster contract -- the one he signed with the Rangers at the beginning of 2001.
That Rangers contract had carried over to New York when Rodriguez was traded to the Bronx Bombers in 2004. But Rodriguez controversially opted out of the final three years -- during Game 4 of the 2007 World Series -- before ultimately re-signing with the Yankees in December. Rodriguez would say that, "All along, I knew I wanted to be a Yankee."
2001: Alex Rodriguez, Rangers -- 10 years, $252 million
When A-Rod signed the first of his two multi-hundred-million-dollar deals, it was the largest contract awarded in professional sports history, doubling Kevin Garnett's $126 million deal signed with the Timberwolves in the NBA in 1997. The blockbuster signing brought Rodriguez from Seattle to Texas at age 25, after he emerged as a superstar shortstop with the Mariners.
Even though the Rangers would go on to trade him to the Yankees after three seasons, Rodriguez played up to his historic contract. He capped his tenure in Texas by winning the American League MVP Award in 2003, and averaged 52 home runs and 132 RBIs in a Rangers uniform, leading the AL in homers every year.
2001: Manny Ramirez, Red Sox -- 8 years, $160 million
This was really just a placeholder in the 2000-01 offseason, between Mike Hampton and Rodriguez. When Manny signed his deal with the Red Sox in December, everyone already knew A-Rod was going to be baseball's first $250 million man. But that deal wasn't official until January. (News of Ramirez's contract actually broke less than 24 hours after A-Rod's.) In Boston, Manny was Manny -- and an elite hitter in the AL for the better part of the next decade who won two World Series rings with the Red Sox.
2001: Mike Hampton, Rockies -- 8 years, $121 million
Hampton held the record for only a short time, as A-Rod finalized his contract with the Rangers just weeks later. But he topped the $116.5 million contract extension Ken Griffey Jr. had signed with the Reds a year earlier and the $105 million free-agent contract another pitcher, Kevin Brown, had signed with the Dodgers the year before that. Of course, Hampton's contract is considered one of the worst in free-agent history -- he lasted just two years with the Rockies, with a 5.75 ERA, before he was traded in November 2002.
1999: Kevin Brown, Dodgers -- 7 years, $105 million
Brown was baseball's first $100 million man. After winning a World Series ring with the shock-the-world Marlins in 1997, then helping the Padres reach the '98 Fall Classic after he was traded to San Diego in the Marlins' post-championship selloff, Brown got his megadeal from the Dodgers that December. Brown's deal eclipsed several other big contracts handed out that offseason -- Mike Piazza's $91 million deal to stay with the Mets (Piazza was eligible for free agency but didn't file), Bernie Williams' $87.5 million free-agent contract with the Yankees and Mo Vaughn's $80 million free-agent deal with the Angels. Brown joined the Dodgers entering his age-34 season and went on to have several productive seasons in Los Angeles.
1999: Bernie Williams -- 7 years, $87.5 million
A fan favorite and key member of the late-1990s Yankees dynasty, Williams almost didn't re-sign with the Bronx Bombers after their historic 1998 season. He wanted a seven-year contract, but the Yankees were only offering five. They almost even lost Williams to the rival Red Sox. But after the Orioles made a $65 million offer to Albert Belle, the Bronx Bombers didn't want to lose out on both outfielders, and George Steinbrenner quickly upped his offer to what Williams was looking for. Bernie stayed in New York and played out his entire career in pinstripes.
1996: Albert Belle, White Sox -- 5 years, $55 million
The baseball world was incensed when the White Sox offered Belle significantly more money than any other club was willing to offer, but that wasn't team owner Jerry Reinsdorf's concern. The South Siders had just seen Belle torment their club with the Indians, cresting with the first (and still only) 50-double, 50-homer season in 1995 and then 48 homers and 148 RBIs the following season.
"It is perfectly fiscally responsible for us to give [Belle] this money," said Reinsdorf. "We have to compete under the system that exists. We have an obligation to our fans to try to win."
Chicago didn't get any closer to a title, but Belle continued to slug on the South Side, nearly replicating his 50-50 feat again in '98 when he hit 48 doubles and 49 homers and drove in 152 runs. But his White Sox tenure ended early thanks to a rare clause in Belle's contract that allowed him to demand that he remain one of the three highest-paid players in each year of the deal. When Belle invoked the clause after that stellar '98 season, the White Sox declined to comply and let him sign with the Orioles in free agency. Just like that, Belle was gone from Chicago.
1992: Barry Bonds, Giants -- 6 years, $43.75 million
"The best should be paid the best," agent Dennis Gilbert said of his client Bonds, and he delivered with a contract worthy of a player coming off two NL MVP Awards in the span of three years. Bonds' total sum shattered baseball's previous high mark of Cal Ripken Jr.'s $32.5 million extension with the Orioles, and his contract brought him back to the city where his father, Bobby, became a star two decades prior.
"This agreement will make Barry Bonds the best-paid player in the game," said Giants owner Peter Magowan. "It is a lot of money, but there is only one Barry Bonds."
That statement would prove prescient, as Bonds went on to win five more MVP Awards, set the all-time home run record and finish with one of the greatest statistical careers in baseball history.
1991: Bobby Bonilla, Mets -- 5 years, $29 million
The Mets signed Eddie Murray and Bonilla in back-to-back weeks, breaking their prior frugal habits with a deal that made Bonilla the highest-paid athlete in North American professional team sports, edging out Knicks center Patrick Ewing by average annual salary. The slugger made two All-Star teams with the Mets, but ultimately couldn't reach his 1991 zenith, when he finished third in NL MVP voting after pacing the league with 44 doubles and helping the Pirates reach Game 7 of the NLCS.
In 2000, the Mets opted for deferred payments that began in 2011 instead of paying Bonilla the $5.9 million he was owed that season. That means Bonilla receives a paycheck worth nearly $1.2 million every July through the year 2035.
1980: Dave Winfield, Yankees -- 10 years and roughly $23 million
It's actually hard to pin down just how much Winfield and Steinbrenner settled on, as the two sides had to be brought back to the negotiating table after there was confusion over the original terms. That was the start of a rocky relationship between the star slugger and owner, as Steinbrenner routinely voiced his displeasure with Winfield's play and was ultimately suspended from baseball after he hired gambler Howard Spira to track down unfavorable details about Winfield.
Through it all, the ultra-athletic Winfield proved to be one of the best hitters of the 1980s, finishing with 205 homers, 818 RBIs and a 134 league-adjusted OPS+ over his nine-year tenure in the Bronx.
1979: Nolan Ryan, Astros -- 4 years, $4.5 million
The Ryan Express became baseball's first million-per-year man with this deal, which brought him to within an hour's drive of his hometown of Alvin, Texas. Ironically, Ryan told the press early in his career that he would buy his own bus ticket to Houston if it meant he could pitch for the Astros.
Ryan's addition formed a superb rotation in Houston including J.R. Richard, Joe Niekro and eventually Don Sutton, and while the Astros never made the World Series with the local fireballer, he did enjoy plenty of personal highlights. The righty tossed his record fifth career no-hitter on Sept. 26, 1981, and racked up 1,866 strikeouts and compiled a 3.13 ERA while wearing Houston's colorful uniform.
1978: Pete Rose, Phillies -- 4 years, $3.2 million
The hit king received all kinds of offers when he made his first foray into free agency: Oil investments from Royals owner Ewing Kauffman, a $100,000-per-year pension plan for life from the Braves, a Budweiser beer distributorship from the Cardinals and two broodmares from the Pirates. The Phillies' initial offer of three years and $2.1 million was actually the lowest offer Rose received, but former club president Bill Giles convinced a local TV station to contribute $600,000 to the cause.
Rose liked how close the Phillies were to a title, having bowed out in the NLCS in each of the previous three seasons. With Rose in tow at first base, Philadelphia would finally capture its first-ever World Series title in the fall of 1980.