The earliest MLB contract extensions

The Red Sox have signed rookie center fielder Ceddanne Rafaela to an eight-year, $50 million contract extension. Rafaela is now part of a select group of players to sign a contract extension with less than a year of big league service time.

Below are notable examples of players who agreed to extensions at very early points in their careers, in order of how much service time they had accrued when they inked those deals:

Colt Keith, Tigers -- January 2024 (Zero days of service time)

After injuries limited Keith to 113 games over his first two Minor League seasons, the infielder stayed healthy and made significant progress in 2023, hitting .306 with 27 homers, 101 RBIs and a .932 OPS over 126 games between Double-A and Triple-A. Fresh off that performance, the Tigers signed him to a contract that could keep him with the organization through 2032, if all three of his club options are exercised. The contract could set up Keith to make his MLB debut early in 2024, less than four years after the Tigers selected him in the fifth round of the 2020 MLB Draft out of high school.

Jackson Chourio, Brewers -- December 2023 (Zero days of service time)

Chourio has quickly ascended Milwaukee’s system since he signed with the team as an amateur free agent out of his native Venezuela in 2021. The 19-year-old has only played six games above the Double-A level, reaching Triple-A for the first time in September '23. However, his relative lack of experience in the high Minors did not stop the Brewers from seeking a long-term contract with the youngster, who features a dynamic skill set with multiple tools that grade out at plus or better. Those tools were on display as he recorded a .283/.338/.467 slash, 22 homers, 91 RBIs and 44 steals over 128 games between Double-A and Triple-A in '23. Chourio became the sixth player to sign a contract extension before his big league debut.

Luis Robert Jr., White Sox -- January 2020 (Zero days of service time)

The White Sox ensured that Robert would remain on the South Side for years to come when they inked the outfielder to a six-year, $50 million extension (with two additional option years) just after New Year's Day. After tearing up Minor League pitching in 2019, hitting .328 with 32 homers and 36 steals as he climbed three levels of Chicago's farm system, Robert debuted in '20 with 11 home runs, a Gold Glove Award in center field and a runner-up finish in American League Rookie of the Year voting. The outfielder earned his first All-Star selection in '23, producing 38 homers, 80 RBIs, 20 steals and an .857 OPS over 145 games.

Evan White, Mariners -- November 2019 (Zero days of service time)

The 23-year-old first baseman secured his future with the Mariners with a deal spanning at least six years. The contract guaranteed White $24 million and included three additional club option years that could take the value to as high as $55.5 million. White, who ranked No. 58 among MLB Pipeline's Top 100 prospects and No. 4 among Mariners prospects at the time of his deal, became just the fourth player in MLB history to sign a long-term contract before reaching the Majors. White won a Gold Glove Award at first base as a rookie in 2020, but he hit just .165/.235/.308 over his first two seasons and hasn't appeared in the Majors since '21 due to injuries. His tenure with the Mariners came to an end when they traded him to the Braves in December '23.

Eloy Jiménez, White Sox -- March 2019 (Zero days of service time)

Jiménez had yet to appear in a big league game at the time of his deal, but that didn't stop the White Sox from giving him a big-time contract. In March 2019, eight days before its season opener, Chicago signed Jiménez to a six-year, $43 million deal that included a pair of club options. The contract made Jiménez, MLB Pipeline's No. 3 overall prospect at the time, just the third player to sign an extension before his MLB debut. It was also the largest contract by total value given to a player in his position. Jiménez grew into his power after a slow start, finishing his rookie year with 31 homers and a .513 slugging percentage. He placed fourth in AL Rookie of the Year voting.

Scott Kingery, Phillies -- March 2018 (Zero days of service time)

Kingery earned the 2017 Paul Owens Award as the Phillies' top Minor League position player after hitting .304/.359/.530 with 26 home runs and 29 stolen bases across the Double- and Triple-A levels. That made the second baseman the only player in the Majors or Minors to record a 25-25 season in '17, and Kingery continued that roll into Spring Training '18, batting nearly .400 and slugging over .700. The infielder's hot spring proved too enticing -- the Phils not only put him on their big league roster to open '18 but also signed him to a six-year, $24 million deal that also included three club options. However, Kingery ended up playing just 325 games for the Phillies -- slashing .229/.280/.387 -- before becoming a free agent when the team declined his '24 club option.

Jon Singleton, Astros -- June 2014 (Zero days of service time)

The Astros were still rebuilding when they inked Singleton to a five-year, $10 million contract and brought him up to the big league roster. The deal made Singleton the first player in history to sign an extension before his MLB debut. The first baseman was the Astros' third-ranked prospect at the time, behind future star Carlos Correa and right-hander Mark Appel, the No. 1 overall pick in the 2013 Draft. Singleton struggled (.620 OPS over 362 plate appearances) in his first callup, however, and played only 114 games with the Astros in '14-15. After logging nary an MLB appearance across '16-22, Singleton returned to the Majors with the Brewers in '23 and even found his way back to Houston after being released by Milwaukee.

Matt Moore, Rays -- December 2011 (17 days of service time)

Moore's extension -- a $14 million deal over five seasons -- was a first for a pitcher, but the Rays saw enough in Moore's first 19 Major League innings to make sure he stuck around in Tampa. Those 19 innings included 10 in the American League Division Series against Texas, when Moore held the Rangers offense to just one run across two outings. The deal was huge for Moore, who had signed for just $115,000 as an eighth-round Draft choice in 2007. Tampa Bay benefited from the extension, too, getting a quality southpaw starter who went 39-28 with a 3.88 ERA -- albeit with some injuries along the way -- before the Rays traded Moore to the Giants at the '16 Deadline.

Evan Longoria, Rays -- April 2008 (24 days of service time)

The Rays transformed from expansion also-rans to AL contenders at this time, and Longoria's incredibly team-friendly contract was a major milestone on that journey. Longoria's six-year, $17.5 million deal certainly seemed a little riskier at the time, given that he had appeared in just six big league games when he signed. But the Rays' timing could hardly have been any better -- Longoria captured the 2008 AL Rookie of the Year Award and led the Rays to their first pennant while hitting 27 homers with 85 RBIs, developing into a perennial All-Star and face of the franchise at third base. Longoria eventually got another six-year, $100 million extension in '12.

Corbin Carroll, D-backs -- March 2023 (38 days of service time)

A monthlong callup at the end of the 2022 season was all the D-backs needed to see from their top prospect to give him a huge long-term deal. In Spring Training '23, Carroll agreed to an eight-year contract extension with Arizona worth a guaranteed $111 million. The outfielder, who earned a rank as MLB's No. 2 overall prospect entering the '23 season, went on to produce 25 homers, 54 steals and a 134 OPS+ over 155 games in the regular season before helping the D-backs make a surprising run to the World Series. He was named the NL Rookie of the Year at the end of the campaign.

Ceddanne Rafaela, Red Sox -- April 2024 (49 days of service time)

Although Rafaela didn't produce much during a 28-game cameo with Boston late in 2023, the Red Sox showed what they think of his potential when they reached an eight-year extension worth $50 million with the outfielder less than two weeks into the 2024 season. Rafaela is an excellent defender in center field and produced 20 homers with 36 steals over 108 games in the Minors in 2023.

Salvador Perez, Royals -- February 2012 (50 days of service time)

Kansas City's front office was already impressed with Perez's stellar defense behind the plate to sign the 21-year-old to a $7 million deal over five years. But Perez proved to be adept with his bat, too, bringing both average and power to go along with his Gold Glove defense. The catcher's incredible durability and personality endeared him to Kansas City fans, and it's safe to say the Royals got more than their money's worth when they originally signed one of baseball's best backstops. Perez's second contract with Kansas City was much larger: a five-year, $52.5 million deal signed in March 2016.

Brandon Lowe, Rays -- March 2019 (58 days of service time)

The Rays saw both offensive and defensive upside in Lowe when they signed him to a six-year, $24 million extension in Spring Training 2019. Lowe quickly made the Rays' front office look smart, with an .862 OPS and 16 homers in 76 games before a bone bruise in his right leg knocked him out of action in July. His half-season performance was still enough to make him an All-Star and place him third in Rookie of the Year voting, and Lowe followed that with back-to-back top-10 MVP finishes in '20 and '21.

Michael Harris II, Braves -- August 2022 (81 days of service time)

The Braves moved to lock up Harris, as well as third baseman Austin Riley, in the same month, creating some certainty for the future with contract extensions for the pair of young stars after extending first baseman Matt Olson during Spring Training. Harris made an immediate impact for the Braves -- on the day he signed his eight-year, $72 million extension, Harris was hitting .287/.325/.500 with 12 homers and 13 steals in 71 games for Atlanta. It only got better from there: he went on to win the NL Rookie of the Year Award.

Wander Franco, Rays -- November 2021 (104 days of service time)

The Rays didn't waste time moving to sign Franco to a long-term deal. After the No. 1 prospect in baseball debuted in 2021 with a historic 43-game on-base streak and third-place Rookie of the Year finish, Franco and Tampa Bay agreed on an 11-year, $182 million contract extension that could turn into 12 years and up to $223 million. Franco's extension is the largest in Rays franchise history as well as the largest ever signed by a player with less than a year of service time. However, the shortstop was placed on administrative leave until further notice in August 2023 through an agreement between MLB and the MLB Players Association after allegations emerged that he had been in an inappropriate relationship with a minor.

Tim Anderson, White Sox -- March 2017 (115 days of service time)

Anderson's six-year, $25 million deal was a record at the time for the largest extension signed by a player with less than one season of big league service time. Anderson had put up a respectable .738 OPS over his first 99 games with the White Sox in 2016. The shortstop struggled to immediately live up to his new contract in '17, hitting .257 and striking out in more than a quarter of his plate appearances, but turned things around in a big way two years later, capturing the AL batting crown with a .335 average.

Paul DeJong, Cardinals -- March 2018 (124 days of service time)

Cody Bellinger's 39-homer season in 2017 partly overshadowed DeJong, who was the runner-up in the NL Rookie of the Year vote after slugging .532 and smacking 25 home runs while providing great defense at shortstop, too. But the Cardinals certainly did notice, inking DeJong to a six-year, $26 million extension in Spring Training '18 that just topped Anderson's record deal. A year later in '19, DeJong hit 30 home runs and made his first career All-Star team, though he followed that up with just 42 homers and a .625 OPS in 347 games from '20-23.

Julio Rodríguez, Mariners -- August 2022 (141 days of service time)

Rodríguez was a sensation even before making his MLB debut on April 8, 2022. During Spring Training, he was tremendous in all facets of the game, leading the Mariners to name him to the Opening Day roster. That was just the beginning, as J-Rod became the fastest AL player to reach 20 homers and 20 steals in his big league career. He also was named an All-Star and put on a show in the Home Run Derby at Dodger Stadium, further cementing his place among the most popular players in the sport. So it was no surprise when news broke that the Mariners were signing him to a contract extension worth a guaranteed 13 years and $210 million. Rodríguez finished the season by leading Seattle to its first playoff appearance in 21 years and running away with the AL Rookie of the Year Award.

Chris Archer, Rays -- April 2014 (156 days of service time)

Archer's six-year, $25.5 million extension re-established the Rays as baseball's most aggressive club in locking up its talented youngsters, after the deals given to Longoria, Moore and James Shields. A fifth-round Draft choice of the Indians in 2006, Archer's path to the Majors was anything but direct. The righty struggled in Minor League ball and was involved in trades to both the Cubs (for Mark DeRosa in '08) and then the Rays (for Matt Garza in '11). Archer found his footing when he rejoined the Rays in June '13, finishing third in the AL Rookie of the Year vote after going 9-7 with a 3.22 ERA in 23 starts. He was traded to the Pirates before the end of his contract in a deal that brought Tyler Glasnow, Austin Meadows and Shane Baz to Tampa Bay in '18.

Ronald Acu?a Jr., Braves -- April 2019 (165 days of service time)

Acu?a's eight-year, $100 million extension (which included a $17 million option and $10 million buyout for both the 2027 and '28 seasons) represented the largest given to a player with his level of service time, but it's looking like a bargain for the Braves, with Acu?a turning into one of baseball's biggest superstars. He made a serious run at the '19 NL MVP Award, knocking 41 homers and coming just three steals shy of recording the fifth 40-40 season in MLB history. While Acu?a tore his ACL in '21, causing him to miss the Braves' run to a World Series title, he did eventually join the 40-40 club -- producing MLB's first 40-homer, 70-steal season -- and win the NL MVP Award in '23.