Since the modern era of free agency began in 1974, Major League Baseball has experienced a series of monumental signings that not only reshaped team rosters but also shifted the power dynamics of the league. These moves, whether through groundbreaking contracts or surprising departures, have left a lasting impact on the sport. Below, we’ll take a look at some of the most significant transactions from 1974 to 2025 that changed the game forever.
2024-25: Juan Soto to the Mets
The Mets, with their deep pockets, were widely considered favorites to land Juan Soto, but the drama surrounding his move was far from ordinary. In an unexpected twist, Soto chose the Mets over the Yankees, with whom he had just gone to the World Series. His 15-year, $765 million deal shattered the record books, surpassing the Yankees’ reported offer of $760 million. This deal not only broke hearts in the Bronx but also sent shockwaves across the baseball world.
2023-24: Shohei Ohtani to the Dodgers
While the Dodgers were long considered front-runners for Ohtani, his secretive negotiations and dramatic twists before signing made the deal even more compelling. After rumors swirled about his possible move to Toronto, Ohtani ultimately signed with the Dodgers for a historic $700 million over 10 years, the largest contract in MLB history at the time. In his first season with L.A., Ohtani delivered a World Series championship, cementing his place as one of the sport’s biggest stars.
2023-24: Craig Counsell to the Cubs
After a stellar nine-year tenure with the Brewers, Craig Counsell shocked the baseball world by leaving for the Cubs, in a divisional shift that made waves. His five-year, $40 million contract with Chicago exceeded the Brewers’ offer, and despite earlier reports linking him to the Mets and Guardians, Counsell’s unexpected move marked a new chapter for the Cubs and their quest for a championship.
2022-23: Carlos Correa Returns to the Twins
Carlos Correa’s free agency was nothing short of dramatic. After a reported 13-year, $350 million deal with the Giants was derailed by a medical review, and another 12-year, $315 million offer from the Mets fell apart, Correa ultimately re-signed with the Twins on a six-year, $200 million deal. This saga highlighted the volatile nature of the market and Correa’s significant value as one of the game’s top shortstops.
2022-23: Jacob deGrom to the Rangers
In one of the offseason’s early surprises, Jacob deGrom signed a five-year, $185 million deal with the Texas Rangers. Despite a history of injuries, deGrom’s ability as one of the league’s top pitchers drew Texas into the mix. Unfortunately, the deal hit a snag when deGrom underwent Tommy John surgery after only six starts, but the signing was still a major splash in a rebuilding Rangers squad.
2021-22: Marcus Semien and Corey Seager to the Rangers
Texas’ commitment to revamping their roster in 2021 resulted in the acquisition of two premium free agents, Marcus Semien and Corey Seager. Semien, coming off a career year with Toronto, inked a seven-year, $175 million contract, while Seager’s deal was even more eye-popping—a 10-year, $325 million pact. Their impact in 2023 helped the Rangers reach the World Series.
2019-20: Gerrit Cole to the Yankees
Gerrit Cole’s $324 million, nine-year contract with the Yankees was a landmark moment in baseball’s pitching market. Moving from the Houston Astros to New York, Cole became the highest-paid pitcher in history and one of the top free agents of his generation, signaling the Yankees’ intent to return to their championship-contending ways.
2018-19: Bryce Harper to the Phillies
Bryce Harper’s 13-year, $330 million deal with the Phillies was the largest in American sports at the time. With no opt-outs or deferred payments, Harper’s decision to sign with Philadelphia symbolized the team’s willingness to make a bold statement in its post-rebuild era. Despite some early questions, Harper would later lead the Phillies to the World Series in 2022.
2018-19: Manny Machado to the Padres
Manny Machado’s 10-year, $300 million deal with the Padres was another franchise-defining move in the 2018-19 offseason. With this signing, Machado became the first MLB player to reach the $300 million mark, a milestone that set the tone for future mega-deals and put San Diego on the map as a rising contender in the National League.
2017-18: Shohei Ohtani to the Angels
Ohtani’s choice to sign with the Los Angeles Angels instead of the Dodgers caught many off guard. The two-way star was drawn to Anaheim’s “family-like atmosphere,” a decision that not only surprised the baseball world but also had a lasting impact on Major League Baseball, as Ohtani’s unmatched skills as both a pitcher and hitter redefined the sport.
2013-14: Robinson Canó to the Mariners
In a shocking move, Robinson Canó left the Yankees after nine seasons to sign a 10-year, $240 million contract with the Mariners. It was a bold move, as Seattle had not made the postseason in over a decade, but Canó’s arrival signified a new direction for the Mariners’ franchise.
2011-12: Albert Pujols to the Angels
After 11 seasons with the Cardinals, Pujols made the surprising decision to sign a 10-year, $254 million deal with the Angels, leaving behind a storied career in St. Louis. The move was one of the largest in MLB history at the time and marked a pivotal moment for the Angels as they aimed to become perennial contenders.
2004-05: Carlos Beltrán and Pedro Martínez to the Mets
In two high-profile moves, the Mets added Carlos Beltrán (seven years, $119 million) and Pedro Martínez (four years, $51.5 million) to their roster. These signings signaled a new era for the Mets, who sought to build a championship-contending team in the mid-2000s.
2003-04: Ivan Rodríguez to the Tigers
Coming off a World Series title with the Marlins, Ivan Rodríguez signed a surprising four-year, $40 million deal with the Tigers, who were in the midst of a rebuild. The move paid off, as Rodríguez helped to catalyze a dramatic turnaround for Detroit, which reached the World Series by 2006.
2000-01: Alex Rodríguez to the Rangers
In 2001, Alex Rodríguez stunned the baseball world by signing a 10-year, $252 million contract with the Rangers, making it the largest deal in sports history at the time. The signing elevated Rodríguez to superstardom and reshaped the future of MLB contracts, setting a precedent for lucrative long-term deals.
2000-01: Manny Ramirez to the Red Sox
Manny Ramirez’s eight-year, $160 million contract with the Boston Red Sox in 2000 was a defining moment for the franchise. His signing helped spark a championship run, and within a few years, the Red Sox would break their 86-year title drought with Ramirez playing a key role.
1998-99: Randy Johnson to the D-backs
In an unexpected move, the Arizona Diamondbacks signed Randy Johnson to a four-year, $52 million deal after their inaugural season. Johnson went on to win four consecutive Cy Young Awards and led the D-backs to a World Series victory in 2001.
1998-99: Kevin Brown to the Dodgers
Kevin Brown made history when he signed a seven-year, $105 million deal with the Dodgers, becoming the first player in baseball history to secure a nine-figure contract. Brown’s deal set the stage for the escalation of player salaries in the years to come.
1996-97: Albert Belle to the White Sox
Albert Belle’s five-year, $55 million contract with the White Sox in 1997 was groundbreaking, as it was the first contract worth over $50 million. This signing was another example of MLB teams beginning to spend big money to acquire top talent.
1994-95: Larry Walker to the Rockies
After the 1994 strike, the Rockies seized the opportunity to sign Larry Walker to a four-year, $22.5 million contract. Walker’s time in Colorado solidified him as one of the game’s greats, benefiting from Coors Field’s hitter-friendly conditions.
1992-93: Greg Maddux to the Braves
Greg Maddux’s unexpected move from the Cubs to the Braves in 1993 was a pivotal moment in the Braves’ ascent to dominance in the 1990s. Maddux’s five-year, $28 million contract set the stage for a rotation that would dominate the NL for years.
1992-93: Barry Bonds to the Giants
Barry Bonds’ six-year, $43.75 million contract with the Giants in 1993 was a game-changer, as Bonds brought his talents to San Francisco, a city with deep ties to his family legacy. This move helped solidify the Giants as a force in the National League.
1980-81: Dave Winfield to the Yankees
In 1980, Dave Winfield signed a 10-year, $23 million contract with the Yankees, making it the largest contract in sports history at the time. Winfield’s move to New York marked a new chapter in the Yankees’ rebuilding efforts, and he became a key player in the team’s return to prominence.
1979-80: Nolan Ryan to the Astros
Nolan Ryan’s four-year, $4.5 million deal with the Astros in 1979 was groundbreaking as it made Ryan the first player to earn over $1 million per year. The move back to his home state of Texas marked the beginning of a lucrative era for MLB players.
1978-79: Pete Rose to the Phillies
Pete Rose’s four-year, $3.24 million contract with the Phillies in 1979 was monumental, making him the highest-paid player at the time. Rose’s leadership helped lead the Phillies to their first World Series championship in 1980.
1976-77: Reggie Jackson to the Yankees
Reggie Jackson’s five-year, $3 million deal with the Yankees in 1977 was a defining moment in MLB history. Jackson’s iconic performance in the World Series that year turned him into a Bronx legend and helped the Yankees clinch their first title in over a decade.
1974-75: Catfish Hunter to the Yankees
In 1974, Catfish Hunter became the first free agent in MLB history after a landmark arbitration ruling. His five-year, $3.75 million deal with the Yankees ushered in the modern era of free agency, laying the foundation for the multi-million dollar contracts that followed.
