Since the first free-agent signing of the modern era back in 1974, there have been several free-agent deals that shook the baseball world and realigned power across the Majors. Here’s a look at several moves that changed the landscape of baseball, and in some cases were downright shocking:
It wasn’t exactly surprising that Cole signed with the Yankees, but the size of his deal, as well as his move from one American League powerhouse — the Astros — to another were monumental. The right-hander was coming off the best season of his career, one in which he finished runner-up in AL Cy Young Award voting to teammate Justin Verlander, and he inked a nine-year, $324 million deal with New York. It was the longest deal ever given to a pitcher, as well as the most valuable.
The Phillies long had been rumored as a possible destination for Harper, since before the slugger even officially became a free agent. Philadelphia was coming out of a rebuilding cycle with money to spend and a fanbase hungry to see its club return to glory.
At times during Harper’s long free agency, there were doubts about whether all of those rumors would come to fruition. When they finally did, the union between the two sides wasn’t so surprising by itself. The fact that Harper not only set a record for the largest financial commitment in MLB history ($330 million), but also signed on for 13 years without any opt-out clauses, certainly raised some eyebrows, though. While opt-outs have become a common feature of contracts for premium free agents, Harper and Philly are tied together into the 2030s.
Even before the 2018-19 offseason started, we knew it would be defined by the Machado and Harper free-agent sweepstakes. After a long winter of waiting, the first winner finally emerged: the Padres, who landed Machado on a record-setting 10-year, $300 million deal.
That made Machado not just baseball’s first $300 million free agent, but the first in the history of the four major North American professional sports — beating Harper to that feat by about a week. The deal could keep the shortstop in San Diego through the 2028 season, putting Machado in position to anchor the team’s talented young core for years to come.
The pursuit of Ohtani, the two-way superstar from Japan who captivated the Majors even before he made his big league debut, was the hottest topic of the offseason. All 30 clubs submitted proposals to Ohtani as to why they would be the ideal fit for the 23-year-old, but the finalists along with the Angels were the Cubs, Dodgers, Giants, Mariners, Padres and Rangers. The fact that Ohtani chose the Angels, particularly over the neighboring Dodgers, who were coming off a World Series appearance, was shocking to many.
In the end, however, a “family-like atmosphere” and a “comfort level” with the organization is what led Ohtani to choose the Halos, according to then-Angels general manager Billy Eppler. Ohtani lived up to the hype, winning the 2018 AL Rookie of the Year Award. Despite missing time due to injury that required Tommy John surgery, he hit .285/.361/.564 with 22 home runs in just 367 plate appearances, while also posting a 3.31 ERA and 30 percent strikeout rate on the mound. And in 2021, he had one of the most incredible seasons in baseball history, becoming the 19th unanimous winner of an MVP Award. Ohtani hit .257/.372/.592 with 46 homers and posted a 9-2 record with a 3.18 ERA and 156 strikeouts in 130 1/3 innings in ’21.
Canó had been a Yankee for all nine seasons of his career when he signed a 10-year, $240 million contract with the Mariners in December 2013. Not only was it a blockbuster move because of the sheer amount and length of the deal, but because Canó left the big stage of New York to join a Seattle franchise that hadn’t been to the postseason since 2001.
For some time, Canó appeared destined to follow in the footsteps of former teammates Derek Jeter, Mariano Rivera and Jorge Posada in spending his entire career with the Yankees. But Seattle’s offer reportedly far exceeded New York’s in both monetary value and length, prompting the second baseman to head to the opposite coast. He slashed .296/.353/.472 with 107 home runs in five seasons with Seattle, and served an 80-game suspension in 2018 after testing positive for a banned substance. He was traded to the Mets following the 2018 season.
A Cardinal for his entire 11-year Major League career to that point, Pujols inked a 10-year, $254 million contract with the Angels in December 2011, a move that stunned the baseball world after it appeared the Cardinals, among a handful of other teams, were favorites to sign the future Hall-of-Fame slugger. The deal was the second-largest in baseball history in terms of average annual value behind Alex Rodriguez’s 10-year, $275 million deal with the Yankees in 2007.
Pujols, the 2001 National League Rookie of the Year Award winner and three-time NL Most Valuable Player Award winner while with St. Louis, was hampered by injuries with the Angels, including foot ailments that have required multiple surgeries. Overall, he hit .256/.311/.447 with 222 homers in parts of 10 seasons with Los Angeles after slashing .328/.420/.617 with 445 homers in 11 seasons with St. Louis. Pujols was released by the Halos in May of 2021 and ended up finishing the season with the Dodgers.
2004-05: Vladimir Guerrero signs with Angels
Guerrero possessed every tool one could want from a Major League player — most especially his light-tower power and a cannon throwing arm from right field — but he perhaps wasn’t as big a star as he should have been while playing for cash-strapped Montreal. The five-year, $70 million deal Guerrero signed with Anaheim changed all that, as the Angels capped an offseason that also saw them add Bartolo Colon, Kelvim Escobar and Jose Guillen by inking the biggest free agent on the market.
While the Angels were ultimately unable to add to their 2002 World Series title with Guerrero in tow, their star acquisition did just about everything else. The slugger hit .337, belted 39 homers and drove in 126 runs to capture the American League MVP Award in his L.A. debut and finished his six-year West Coast tenure with four All-Star selections and 137 dingers. In 2018, Guerrero became the first Hall of Fame player to don an Angels cap on his plaque in Cooperstown.
2004-05: Carlos Beltrán, Pedro Martinez sign with Mets
Martinez had accomplished just about everything he could in Boston, putting together two of the greatest pitching seasons in history in 1999 and 2000 before helping the Red Sox capture their first World Series title in 86 years in ’04. Omar Minaya had begun his tenure as the Mets’ general manager just weeks before he took advantage of rocky negotiations between Martinez and the Red Sox, swooping in to sign the future Hall of Famer to a four-year, $51.5 million deal that sent shockwaves through the sport.
“We were willing to go the extra year and until then the Red Sox weren’t,” Minaya later recounted. “When they did, it was too late.”
Martinez showed he had plenty left in the tank, going 15-8 with a 2.82 ERA in his first season in Queens before injuries began to set in. The righty made just 48 starts over the final three years of his contract with New York before moving on to his final season with the Phillies.
Beltrán, meanwhile, was coming off one of the greatest postseason performances of all time for the Astros when he signed a seven-year, $119 million deal with the Mets in January 2005. The Royals traded Beltrán to the Astros in June 2004 as part of a three-team deal, and he went on to hit .435 with three doubles and eight homers between the NL Division Series and NL Championship Series as Houston fell a game short of reaching the World Series. The New York Times reported that it was the Martinez deal that helped convince Beltrán to join the Mets.
In his seven seasons with New York, Beltrán hit .280/.369/.500 with 149 home runs. In 2011, he was traded to the Giants in the deal that sent Zack Wheeler to New York. Beltrán then played two seasons with the Cardinals, two-plus seasons with the Yankees and a season with the Rangers before returning to Houston to help the Astros win the World Series in 2017.
2003-04: Ivan Rodriguez signs with Tigers
Coming off a season in which he helped the upstart Marlins defeat the Yankees in the World Series, Rodriguez was a free agent catcher entering his age-32 season with back issues. That caused him to remain on the market through the holidays that offseason, but the Tigers made a surprising four-year, $40 million offer to the 10-time All-Star. The signing turned out to be the beginning of a rejuvenation for the club, serving as a catalyst for other moves that would follow to take the franchise from a 119-loss season in 2003, to the World Series by 2006.
Rodriguez never went on the injured list during his five-year run with Detroit, hitting .298/.328/.449 and being named an AL All-Star four straight seasons from 2004-07.
2000-01: Alex Rodriguez signs with Rangers
Rodriguez landed the largest contract in sports history — doubling the size of NBA star Kevin Garnett’s deal with the Minnesota Timberwolves — when he signed a 10-year, $252 million deal with the Rangers in January 2001. At age 25, Rodriguez was the brightest young star in the game, having hit .309/.374/.561 with 189 home runs and 133 steals in five full seasons with the Mariners.
Rodriguez put up big numbers, as expected, with Texas, slashing .305/.395/.615 with 156 homers in three seasons before the Rangers traded him to the Yankees. Following the 2007 season, Rodriguez opted out of the final three years on his contract, and later re-signed with the Yankees on a new record 10-year, $275 million contract. In a 22-year career, Rodriguez finished with 696 home runs and a .930 OPS. He was a three-time AL MVP Award winner and a 14-time All-Star.
2000-01: Manny Ramirez signs with Red Sox
In a truly franchise-altering move, Boston signed Ramirez to an eight-year, $160 million contract in December 2000. It came as a surprise in many quarters that Ramirez would leave his comfort zone in Cleveland, where he established himself as a slugging star over the first eight seasons of his career. While Cleveland’s offer to re-sign him was a strong one, Boston won out, and within four years, Ramirez would join with David Ortiz and Pedro Martinez, among other later signings to bring the city its first World Series title since 1918.
Ramirez was the MVP of the 2004 World Series, in which the Red Sox swept the Cardinals. Overall, in eight years with Boston, he hit .312/.411/.588 with 274 home runs. He also helped the 2007 club win the World Series with a sweep of the Rockies.
1998-99: Randy Johnson signs with D-backs
The D-backs were fresh off their inaugural season, in which they lost 97 games, when they signed a 35-year-old Johnson to a four-year, $52 million contract. The move was considered curious by many, given that Arizona was an expansion franchise and Johnson would be under contract through the age of 38. But the skepticism proved to be wrong when Johnson went on to win four consecutive NL Cy Young Awards and helped lead Arizona to the 2001 World Series title in seven games over the Yankees.
Johnson was named co-MVP along with Curt Schilling for the World Series, coming on in relief during Game 7 after having started Game 6, and tossing 1 1/3 scoreless frames before the D-backs won on a Luis Gonzalez walk-off single off Mariano Rivera in the ninth inning. In all, the Big Unit spent six seasons with Arizona in his first stint with the club (he would return for two more seasons from 2007-08), posting a 2.65 ERA and 11.9 strikeouts per nine innings.
1998-99: Kevin Brown signs with Dodgers
Brown made history in December 1998 when he signed a seven-year deal that made him the first $100 million player in baseball history. The right-hander was entering his age-34 season, but he was also coming off a stellar season with the Padres in which he went 18-7 with a 2.38 ERA and helped San Diego capture its second pennant in franchise history.
The deal was not popular among rival executives who were less eager to begin handing out nine-figure deals — especially to a pitcher — but the Dodgers defended the move by pointing to the huge contracts handed out to players like Mike Piazza and Mo Vaughn that set the escalating precedent.
“We’re getting criticized because we were the most recent ones,” argued then-Dodgers general manager Kevin Malone. “The fact of the matter is that we’re just falling in line with what our competitors have done.”
Brown had some high points during his Dodgers tenure, including 18 wins in his debut season and an ERA title in 2000, but injuries prevented him from fulfilling the full value of his record deal. Los Angeles traded Brown to the Yankees in December 2003, but he continued to struggle to stay on the field on a full-time basis before ultimately retiring in ’06.
1996-97: Albert Belle signs with White Sox
White Sox owner Jerry Reinsdorf flexed his financial muscles by inking Belle to a record five-year, $55 million contract in a move that pulled the slugger away from Cleveland, Chicago’s AL Central rival. Belle’s prior two seasons in Cleveland were something to behold: A 52-double, 50-homer combo in 1995 followed by 148 RBIs in ’96 that established the left fielder as one of the game’s premier sluggers.
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, before he invoked an unusual clause in his contract that allowed him to demand that he remain one of the three highest-paid players in baseball. The White Sox declined Belle’s demand, instead letting him leave via free agency, through which he signed another megadeal with the Orioles.
1994-95: Larry Walker signs with Rockies
The 1994 players’ strike forced the Expos to cut payroll, meaning Montreal had to say goodbye to its talented right fielder. The Rockies swooped in and signed Walker to a four-year, $22.5 million deal shortly after the work stoppage concluded, and their new acquisition took full advantage of the halcyon hitters’ environment of pre-humidor Coors Field. Walker’s OPS would sit above .900 in all but one of his nine full seasons in Denver as he made four All-Star teams and captured the ’97 NL MVP. He was elected to the Hall of Fame on his 10th and final ballot in 2020.
1992-93: Greg Maddux signs with Braves
Maddux was the reigning NL Cy Young Award winner in the winter of 1992, a free agent after spending the first seven seasons of his career with the Cubs. It was expected that the Yankees would land the right-hander, but in a surprise twist, it was Atlanta that inked Maddux to a five-year, $28 million contract on Dec. 9 during the Winter Meetings. While the contract was for less than what New York was offering, Maddux wanted to join what would become one of the greatest starting rotations in baseball history with Tom Glavine, John Smoltz and Steve Avery.
Maddux would go on to become the best starting pitcher of the 1990s, and indeed one of the best in baseball history. The Hall of Famer won three consecutive NL Cy Young Awards from 1993-95 for Atlanta, making it four straight overall. He helped the Braves win the 1995 World Series over a powerhouse Cleveland club for the franchise’s first championship in Atlanta. Maddux also won 10 consecutive NL Gold Glove Awards with the Braves, and in 11 seasons had a 2.63 ERA.
1992-93: Barry Bonds signs with Giants
In a move that was more monumental than surprising, Bonds left the Pirates and joined the team his father, Bobby, had starred with from 1968-74. Bonds’ godfather is Giants legend Willie Mays, and Bonds grew up in the Bay Area while his father played for San Francisco. The Giants were nearly sold and moved to Florida following the 1992 season, but a new ownership group purchased the team and kept it in San Francisco, giving it a jump-start by landing Bonds — a two-time NL MVP Award winner — with a six-year, $43.75 million contract.
The Bonds signing was a catalyst in vaulting the Giants to a 103-win season in 1993, and eventually four postseason appearances over the next decade. Bonds would win five more NL MVP Awards and hit 586 of his all-time record 762 home runs in 15 seasons with San Francisco. He was named to 12 All-Star teams over that span, and won six of his eight career NL Gold Glove Awards. During his tenure with the Giants, the franchise built a new waterfront ballpark and came within one victory of winning the World Series in 2002.
1991-92: Bobby Bonilla signs with Mets
Mets general manager Al Harazin characterized his club’s back-to-back acquisitions of Eddie Murray and Bonilla as a “staggering parlay” when Bonilla inked his five-year, $29 million deal. Bonilla’s $5.8 million average annual salary made him the highest-paid athlete in North American professional team sports, edging him ahead of Knicks center Patrick Ewing.
Bonilla 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. New York traded him to Baltimore just before the Trade Deadline in 1995, but got him back in a deal with the Dodgers in November 1998. In 2000, the Mets released Bonilla and worked out a deal with his agent to defer the final $5.9 million on his deal. Beginning in 2011, Bonilla began receiving a paycheck worth nearly $1.2 million every July 1 that lasts through the year 2035.
1980-81: Dave Winfield signs with Yankees
In what was at the time the richest contract in sports history, Winfield signed with the Yankees for 10 years and $23 million in December 1980. The big slugger had spent his entire eight-year career to that point with the Padres, having hit 154 homers while stealing 133 bases for San Diego. Winfield hit 205 home runs with an identical 134 OPS+ in nine seasons with New York before the Yankees traded him to the Angels in 1990. Despite his productivity, along with other stars such as Don Mattingly during the decade, the Yankees never made the postseason during Winfield’s time with the club after an appearance in the 1981 World Series.
1979-80: Nolan Ryan signs with Astros
Ryan began his career with the Mets and made a name for himself with the Angels, but he returned to his home state by signing a four-year, $4.5 million contract with the Astros, just 25 miles north of his hometown of Alvin, Texas, in November 1979. With the contract, he became the first player in MLB history to earn more than $1 million in a single season. In nine seasons with Houston, Ryan compiled 1,866 strikeouts with a 3.13 ERA, setting an MLB record by tossing his fifth career no-hitter on Sept. 26, 1981 vs. the Dodgers. Ryan also anchored the starting rotations of the franchise’s first two postseason clubs in 1980 and ’86.
Ryan would go on to play five more seasons with the Rangers after his tenure in Houston, and finished his career with seven no-hitters and a record 5,714 strikeouts. Though he played for four different teams in his 27-year career, Ryan’s contract with the Astros paved the way for lucrative deals for future free agents after he broke the $1 million per year barrier in 1979.
1978-79: Pete Rose signs with Phillies
Philadelphia couldn’t get past the NL Championship Series in three consecutive years from 1976-78, so the club entered into a competitive field for Rose with hopes of adding a fiery leader. The all-time hit leader received plenty of tempting offers — including incentives such as a stake in Royals owner Ewing Kauffman’s oil investments and the Braves’ offer of a $100,000-per-year pension for life — but Rose ultimately chose the Phillies thanks to their already-competitive roster.
“They were the closest team to get where I wanted to be at that stage of my life,” Rose later recounted, “and that was the World Series.”
Rose’s four-year, $3.24 million contract made him the highest-paid player in the game, and he helped lead the Phillies to their first World Series title in 1980, followed by another NL pennant in ’83.
1976-77: Reggie Jackson signs with Yankees
The Yankees won 97 games in 1976, but they were also swept by Cincinnati’s “Big Red Machine” in that year’s World Series. So, shortly after Thanksgiving, they added one more superstar in Jackson — the ’73 AL MVP who had already contributed to three World Series championship clubs in Oakland before clubbing 27 homers for the Orioles in ’76 — to help them get over the hump. Jackson’s five-year, $3 million deal with New York ushered in one of the wildest periods in Yankees history, but ultimately a successful one, too. Jackson memorably homered in three straight at-bats in Game 6 of the following year’s World Series to become a Bronx legend, and the Yankees defeated the Dodgers in back-to-back Fall Classics.
1974-75: Catfish Hunter signs with Yankees
Following a dispute with Oakland A’s owner Charlie Finley in 1974, an arbitrator ruled Hunter to be a free agent, the first such designation of a Major League Baseball player in more than a century. Hunter ultimately signed a landmark five-year, $3.75 million deal (with a $1 million signing bonus) with the Yankees on New Year’s Eve, opening the door for what would become MLB free agency over the decades that would follow.
Hunter helped the Yankees restore their fortunes as baseball’s best club, reaching the World Series each year from 1976-78, and winning back-to-back titles in ’77 and ’78. The Hall of Famer finished out his 15-year career with the Yankees, posting a 3.58 ERA over five seasons for New York.