Biggest February Free-agent Signings In MLB (

Think all of the biggest free-agent signings happen at December’s Winter Meetings? Think again.

Some of the biggest free agents in recent years have waited until February to ink their massive, nine-figure deals. In fact, there have been plenty of notable February deals, both in terms of dollars and impact, in the history of MLB free agency. This year, a number of high-profile free agents including Trevor Bauer, Marcell Ozuna and Nelson Cruz could sign big deals in the month of February.

Here are the biggest February free-agent signings.

Feb. 21, 2019: Manny Machado signs with Padres for 10 years, $300 million
The hype surrounding the impending free agencies of both Machado and fellow 26-year-old superstar Bryce Harper dominated headlines as far back as the 2018 regular season, with both players expected to sign market-altering contracts. Each deal took a long time to develop (Harper didn’t sign with the Phillies until March), but Machado signed first when he agreed to a $300 million deal — briefly setting a

, before Harper signed for $330 million — with the Padres.

San Diego opened its wallet for this generational infield talent with the intention of seriously contending for the first time in more than a decade, and while it took a season for Machado to settle in (.796 OPS in 2019), that ascension now looks firmly underway. The Padres became MLB’s most exciting up-and-coming team in 2020, and Machado, paired with young superstar shortstop Fernando Tatis Jr. on the left side of the infield, returned to form with a .950 OPS and 16 homers over the 60-game season.

Feb. 26, 2018: J.D. Martinez signs with Red Sox for five years, $110 million
Sometimes, last-minute shopping pays big dividends. Martinez had seemed like a great fit for Boston all along, with the Red Sox having struggled to generate power in 2017, when Martinez blasted 45 home runs in 119 games for the Tigers and D-backs. Finally, the two sides came together on a deal that gave the slugger the chance to opt out after the 2019, ’20 or ’21 seasons.

Martinez already cemented his place in Red Sox history by batting .330/.402/.629 with 43 home runs and an MLB-high 130 RBIs in his first season in Boston. He continued to rake in the postseason, as the Sox cruised to a championship.

Feb. 19, 2018: Eric Hosmer signs with Padres for eight years, $144 million
Coming off a 71-91 season and without a postseason appearance since 2006, San Diego sought to energize its rebuild by landing Hosmer. The first baseman was just 28 years old and had experience helping to lift a club from the basement to the World Series during his time in Kansas City. Despite how long Hosmer remained on the market, the Padres had to give out the largest contract in franchise history.

The marriage didn’t go as planned in Years 1 and 2 (combined 97 OPS+), but Hosmer rebounded in a major way in the shortened 2020 season, slugging a career-best .517 while helping to lead San Diego to the NLDS.

Feb. 13, 2018: Yu Darvish signs with Cubs for six years, $126 million
Darvish signed the biggest deal of any free-agent pitcher in the winter of 2017-18, jumping from Los Angeles to Chicago ahead of his age-31 season. The right-hander was coming off his fourth career All-Star year and third 200-strikeout season, and even though he had an up-and-down postseason with the Dodgers, he was still the only pitcher to get a nine-figure contract that offseason.

Unfortunately, Darvish’s Cubs debut season couldn’t have gone much worse. Plagued by arm trouble — first right triceps tendinitis, then a triceps strain and stress reaction in his elbow that ended his rehab effort in August — Darvish was limited to just eight starts. Even when he was on the field he struggled, posting a career-high 4.95 ERA. But Darvish began turning things around with an electric second half to 2019 and kept that roll going into ’20, when he finished runner-up for the NL Cy Young Award by going 8-3 with a 2.01 ERA and 93-to-14 strikeout-to-walk ratio. The Cubs then turned an eye toward the future and traded Darvish to the Padres for right-hander Zach Davies and four Minor Leaguers.

Feb. 11, 2015: James Shields signs with Padres for four years, $75 million
Shields’ deal was part of a massive slate of offseason moves by the Padres entering 2015, which also included adding Matt Kemp, Justin Upton and Wil Myers. The 33-year-old right-hander was coming off a successful four-year stretch with the Rays and Royals, when between 2011-14, he twice placed in the AL Cy Young Award voting, placed in the ’11 AL MVP Award voting and made the AL All-Star team that season. Shields had also started for four postseason teams in his nine big league seasons, including Kansas City’s AL pennant-winning team in 2014. His signing, though, was one that did not pan out for San Diego. Shields was solid enough in his first season with the Padres, going 13-7 with a 3.91 ERA and hitting the 200-inning and 200-strikeout marks, but he went through a major decline after that and was traded to the White Sox during the ’16 season.

Feb. 24, 2014: Nelson Cruz signs with Orioles for one year, $8 million
Only about a week after handing out a $50 million contract to Ubaldo Jiménez, the Orioles pulled off a huge steal. Cruz was coming off a 50-game suspension the previous season that resulted from the Biogenesis investigation, but the 33-year-old had averaged 27 home runs in his previous five years with the Rangers and had helped lead them to two World Series appearances. Cruz gave Baltimore a middle-of-the-order bat the team badly needed, and the signing paid off big time. Cruz crushed a Major League-leading 40 home runs for the O’s in 2014, made the AL All-Star team, finished seventh in the AL MVP Award voting and helped lead Baltimore to the ALCS.

Feb. 19, 2014: Ubaldo Jimenez signs with Orioles for four years, $50 million
Jimenez, a former All-Star and third-place NL Cy Young Award finisher with the Rockies, was coming off a major bounceback season with the Indians when he hit free agency after 2013. The 30-year-old had just gone 13-9 with a 3.30 ERA in 32 starts for the Tribe, with 194 strikeouts in 182 2/3 innings. The Orioles, meanwhile, had been seeking a starting pitcher for the entire offseason. The match was finally made in February, with Baltimore giving Jimenez its largest free-agent starting-pitcher contract to that point. Jimenez had a rocky tenure with the O’s — though he averaged 149 innings over his four years with the team — going 32-42 with a 5.22 ERA.

Feb. 15, 2013: Michael Bourn signs with Indians for four years, $48 million
Bourn hit free agency on a run of four straight years with 40-plus steals, including three straight league-leading totals of 61, 52 and 61 from 2009-11. A two-time NL All-Star and a Gold Glove winner, the 30-year-old declined a qualifying offer from the Braves to test free agency, but the Indians’ top Draft pick was protected, giving them an advantage in signing the speedster.

Bourn battled right index finger and left hamstring injuries during his first year in Cleveland, and although the Indians made the AL Wild Card Game, he stole just 23 bases on the year and never really rediscovered his old form in the following seasons.

Feb. 13, 2012: Yoenis Céspedes signs with A’s for four years, $36 million
It was in February 2012 that the A’s won the Cespedes sweepstakes, beating out six other teams for the Cuban outfielder’s services. The deal might have been a risk at the time, but it proved to be a great one for the A’s. Cespedes came to the big leagues as a 26-year-old and blossomed into a star immediately. As a rookie, he hit .292 with 23 homers and 82 RBIs and finished as the AL Rookie of the Year Award runner-up and 10th in the AL MVP Award voting. Cespedes anchored postseason lineups in each of his first two seasons in Oakland before being traded to the Red Sox in the Jon Lester deal at the 2014 non-waiver Trade Deadline.

“I’m very happy to be here,” Cespedes said after first arriving at the A’s Spring Training facility, “because I feel I’m very close to my dream to play in the big leagues.”

Feb. 18, 2011: Vladimir Guerrero signs with Orioles for one year, $8 million
The Hall of Famer was a 15-year veteran when he signed with the Orioles, but he was also coming off an All-Star 2010 season with the Rangers in which he had also won an AL Silver Slugger Award, finished 11th in AL MVP Award voting and helped Texas make the World Series. Baltimore gave Guerrero a one-year deal for 2011, and he hit .290 with 13 homers for the O’s in 145 games, but it would be the final season of his illustrious big league career. Guerrero would officially retire in 2014 as an Angel.

Feb. 11, 2009: Adam Dunn signs with Nationals for two years, $20 million
Dunn was coming off five straight 40-homer seasons with the Reds when he entered free agency at age 29. But like several players now, Dunn hit a slow market. As Spring Training approached, the Nationals were the team that finally landed him. The Nats were still building up the team in the two seasons Dunn played for them, but he provided a ton of power, homering 38 times both years.

“I can look you in the eye,” Dunn said at his introductory news conference, “and honestly say this is where I wanted to be.”

Feb. 15, 2007: Barry Bonds re-signs with Giants for one year, $15.8 million
The 42-year-old Bonds was chasing MLB’s all-time home run record in 2007, having finished the ’06 season just 22 shy of Hank Aaron’s 755. The legendary but controversial hitter had to nail down one final contract to get his shot. He and the Giants finally agreed to a one-year deal at the very end of January, but MLB made them slightly rework the terms and it wasn’t finalized until mid-February. On Aug. 7 of that season, Bonds made history. He drove home run No. 756 deep to right-center field at AT&T Park, setting a new Major League record.

Feb. 14, 2007: J.D. Drew signs with Red Sox for five years, $70 million
Opting out of the final three years of his contract with the Dodgers paid dividends for Drew after the 2006 season. Drew and the Red Sox actually agreed to a contract in December and finalized it at the end of January, but it had to be reviewed by MLB and he wasn’t officially added to the roster until February. Some thought Drew was overpaid, but he was a productive player in his years with Boston and had some especially huge hits in the postseason. Maybe the biggest came in his first season, when Drew’s grand slam in Game 6 of the AL Championship Series helped the Red Sox stave off elimination at the hands of the Indians. Boston went on to win that series in seven games and the World Series in a clean sweep over the Rockies.

Feb. 7, 2005: Magglio Ordonez signs with Tigers for five years, $75 million
A year after they brought in Pudge, the Tigers netted another big free agent late in the game. That was Ordonez, who was the last marquee name available that offseason when Detroit got him. The 31-year-old was a four-time All-Star and two-time AL Silver Slugger Award winner with the White Sox, and he had placed in the Top 20 in AL MVP Award voting three times, but he was coming off an injury-shortened season when he hit free agency. That didn’t stop Detroit, and Ordonez gave the Tigers another pair of All-Star years and an AL MVP Award runner-up finish in 2007, while also being a key contributor for the team that made the ’06 World Series. He would be a Tiger for the rest of his career.

Feb. 6, 2004: Ivan Rodriguez signs with Tigers for four years, $40 million
Pudge won the World Series with the Marlins in 2003 — and he was a 10-time All-Star and former AL MVP Award winner with the Rangers before that — but when the 32-year-old went into free agency that offseason, he didn’t sign a new contract until early February. That’s when the Tigers, rebuilding after a 119-loss season, convinced the Hall of Fame catcher to come to Detroit. With Rodriguez behind the plate, the Tigers became contenders again within just a few seasons. He opened his tenure in Detroit with four straight AL All-Star seasons, won three AL Gold Glove Awards, an AL Silver Slugger Award, and he helped the Tigers reach the 2006 World Series. It was arguably the most important free-agent signing in franchise history.

“During that offseason, we had a very good conversation with [general manager] Dave Dombrowski,” Rodriguez would later recall. “Dave told me and my agent, ‘I promise you that I’m going to put a really good team together, and in three years, you’re going to be in the World Series again.’ And that’s exactly what happened.”

Feb. 13, 1995: Dodgers sign Hideo Nomo to Minor League deal with $2 million signing bonus
Moving from Nippon Professional Baseball to MLB is commonplace now, but in 1995, Nomo became the first Japanese-born player to come to the Major Leagues since Masanori Murakami, the first from Japan, in 1964. His first year in Los Angeles, the right-hander whose unique delivery earned him the nickname “The Tornado” led the NL with 206 strikeouts and finished second with a 2.54 ERA. He started the All-Star Game, throwing two scoreless innings, and after the season, he won the NL Rookie of the Year Award. Nomo’s success in the Majors helped pave the way for the many Japanese-born players who have made the jump since.

“We all learned in grammar school that East is East, and West is West, and never the twain shall meet,” legendary Dodgers broadcaster Vin Scully said at Nomo’s introductory news conference. “That is put to rest today.”

Feb. 5, 1991: Jack Morris signs with Twins for one year, $3 million
The Hall of Famer had spent the first 14 seasons of his career with the Tigers when he hit free agency following the 1990 season. Morris was the winningest pitcher of the ’80s, a four-time All-Star and World Series champion in ’84. But it took him until February to sign with the Twins on a one-year deal after turning down a three-year, $9.3 million offer to stay in Detroit. Morris went on to have an All-Star season at age 36 in ’91, and he led the Twins to a World Series title, capped by his legendary 10-inning shutout of the Braves in Game 7.

“He brings us 240 quality innings,” Twins manager Tom Kelly said at the time of the signing. “That gives us somebody to look at if things are going bad: ‘Let Jack pick us up tonight.’ It helps the bullpen. It gives our young pitchers someone to look up to.”

Other notable February free-agent deals
February 25, 2019: Marwin Gonzalez signs with Twins for two years, $21 million
February 24, 2017: Matt Wieters signs with Nationals for two years, $21 million
February 16, 2017: Mike Napoli signs with Rangers for one year, $8.5 million
February 29, 2016: Ian Desmond signs with Rangers for one year, $8 million
February 25, 2016: Dexter Fowler re-signs with Cubs for one year, $8 million
February 25, 2016: Yovani Gallardo signs with Orioles for two years, $22 million
February 4, 2016: Howie Kendrick signs with Dodgers for two years, $20 million
February 16, 2014: A.J. Burnett signs with Phillies for one year, $16 million
February 14, 2014: Fernando Rodney signs with Mariners for two years, $14 million
February 7, 2014: Francisco Rodríguez re-signs with Brewers for one year, $3.25 million
February 6, 2014: Justin Turner signs with Dodgers on Minor League deal
February 18, 2009: Ken Griffey Jr. returns to Mariners on one year, $2 million deal
February 20, 2010: Johnny Damon signs with Tigers for one year, $8 million
February 12, 2009: Bobby Abreu signs with Angels for one year, $5 million
February 15, 2002: Tigers sign Dmitri Young for four years, $28.5 million
February 28, 1985: Rick Reuschel signs with Pirates on Minor League deal, then wins NL Comeback Player of the Year Award

David Adler is a reporter for based in New York. Follow him on Twitter at @_dadler. Matt Kelly is a reporter for based in New York. Follow him on Twitter at @mattkellyMLB.

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