Free-agent signings that shook up MLB

December 9th, 2023

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.

2023-24: signs with Dodgers

In the bigger picture, there was nothing too shocking about Ohtani signing with the Dodgers, a team with deep pockets and a long-held interest in acquiring him. A finalist for Ohtani before he signed with the Angels in 2017, the Dodgers were considered by most to be the favorites this time around. No, what's shocking is how everything transpired in the week or so before the deal was finalized -- and then the ultimate terms of that deal. Ohtani's secretive process kept fans and media buzzing (and guessing) throughout the Winter Meetings, which concluded with Ohtani still on the market. A couple of days later, one report had Ohtani choosing the Blue Jays over the Dodgers -- and others had him at least heading to Toronto on a private plane. Others refuted that. Confusion reigned. 

Then, just one day later, we had a resolution. It was the Dodgers after all. And not only did L.A. reel in its big fish with the largest free-agent contract in MLB history ($700 million over 10 years), it nearly doubled the previous record in doing so.

2023-24: Craig Counsell leaves Brewers for Cubs

The first big splash of the 2023-24 offseason came from Counsell, who spent nine years as the manager of the Brewers before leaving them in free agency to take on the same role with divisional-rival Chicago Cubs, who pried Counsell away with a landscape-altering five-year, $40 million deal (the Brewers reportedly offered him a contract that would have paid him $5 million a season). Counsell guided the Brewers to three division titles, five playoff appearances and a 707-625 record (.531 winning percentage) in the regular season during his nine years with the club. 

His deal with the Cubs came out of left field, as Counsell was known to have met with the Guardians and Mets about their managerial vacancies, with most assuming that he'd go to the Mets to work with his former boss, David Stearns. But then he and the Cubs shocked the baseball world, as he joined a Cubs team that already had previous manager David Ross under contract through the '24 campaign.

2022-23: signs with Twins

Correa's first contract with the Twins, signed a year earlier, was shocking enough. But when he opted out after the 2022 season, things got much, much wilder.

First, Correa seemed to be headed to the Giants on a reported 13-year, $350 million deal. However, three hours before San Francisco was set to introduce him at Oracle Park, the club postponed its scheduled press conference as it reviewed Correa's medicals. Then, the Mets swooped in, reaching a 12-year, $315 million contract with Correa early the next morning -- but then that agreement also reportedly hit a snag in reviewing Correa's physical. After three weeks of trying to get the deal to the finish line, news broke that Correa had reached yet another agreement: A six-year deal worth $200 million with the Twins that also includes team options for each year between 2029-32. This time, Correa passed his physical, the deal got to the finish line, and after so many twists and turns, the star shortstop returned to Minnesota.

2022-23: signs with Rangers

While the Rangers were certainly rumored to be in the mix for the two-time Cy Young Award winner, it was still a stunner when Texas inked deGrom to a five-year, $185 million contract in early December. It was the first big free-agent signing of the offseason, and it was a blockbuster. deGrom, considered by many to be the best starting pitcher on the planet when healthy, was limited to 26 starts over two seasons from 2021-22, due to an assortment of injuries, including shoulder and elbow problems. But Texas made a big splash for the second consecutive offseason (see below). This one hit an early speed bump, as deGrom made just six starts for the Rangers before undergoing Tommy John surgery.

2021-22: and sign with Rangers

Semien bet on himself and came out on top. The 31-year-old infielder signed a one-year pact with Toronto after an abbreviated 2020 season and proceeded to hit .265/.334/.538 with 45 home runs and 102 RBIs across 162 games played for the Blue Jays. After finishing third in AL MVP voting, the California native cashed out on his stellar stats by inking a seven-year pact with the Rangers worth $175 million. But that wasn't even the biggest deal Texas struck for a middle infielder on Dec. 1, 2021 -- an honor that went to Seager's seven-year, $325 million contract that was announced on the same day. While that highly aggressive maneuver didn't pay off immediately -- the Rangers lost 94 games in 2022 -- Seager and Semien helped push the team into the World Series in '23.

2019-20: signs with Yankees

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.

2018-19: signs with Phillies

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.

2018-19: signs with Padres

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.

2017-18: signs with Angels

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.

2013-14: signs with Mariners

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. 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. 

2011-12: signs with Angels

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.

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."

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 New York Times reported that it was the Martinez deal that helped convince Beltrán to join the Mets.

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.

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.

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.

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.

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.

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 premium sluggers.

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.

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.

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.

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. 

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. 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.

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. 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.