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Revisiting the earliest MLB contract extensions

Jimenez becomes third player to sign deal before debut
March 20, 2019

Eloy Jiménez has yet to appear in a big league game, but he's already finalizing a big-time contract. The sport’s No. 3 overall prospect, according to MLB Pipeline, worked out a long-term deal with the White Sox on Wednesday, eight days before the club opens the 2019 season at Kansas

Eloy Jiménez has yet to appear in a big league game, but he's already finalizing a big-time contract.

The sport’s No. 3 overall prospect, according to MLB Pipeline, worked out a long-term deal with the White Sox on Wednesday, eight days before the club opens the 2019 season at Kansas City. The pact will include a guaranteed $43 million over six years, according to a source, with the value rising as high as $77.5 million if the Sox exercise a pair of club options.

It's a historic deal, because it would set a record for the largest contract awarded to a player in Jimenez's position, making him just the third player to sign an extension before his MLB debut.

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:

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

Originally signed by the Cubs out of the Dominican Republic in 2013, Jimenez came to the White Sox as part of a July 2017 trade that sent pitcher Jose Quintana to the North Side of Chicago. Jimenez solidified his status as a top prospect 2018, his first full season in the White Sox system, batting a combined .337/.384/.577 with 22 homers in 108 games split between Double-A Birmingham and Triple-A Charlotte.

That performance put Jimenez on the doorstep of the Majors. The White Sox seemed ready to delay that debut when they optioned the slugging outfielder to Triple-A during Spring Training, but about a week later, the two sides agreed to their deal.

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 an excellent all-around season in which he hit .304/.359/.530 with 26 home runs, 29 doubles, eight triples and 29 stolen bases across the Double- and Triple-A levels. That made the second baseman the only player in the Major or Minor Leagues to record a 25-homer, 25-steal season in '17, and Kingery continued that roll into 2018, batting nearly .400 and slugging over .700 in Grapefruit League play.

Phillies manager Gabe Kapler envisioned the 23-year-old carrying a utility role with his club, and Kingery's hot spring proved too enticing to deny the youngster a roster spot -- and ultimately too enticing to not lock him down long-term. The result was a six-year, $24 million deal that also includes three club options. While Kingery still has plenty of time to make good on that potential, he struggled as a rookie, batting .226/.267/.338 over 147 games.

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

The Astros were still on their way up from the ground floors of their rebuilding efforts 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's deal reflected the Astros' mindset at the time in terms of signing club-friendly deals with their youngsters. In 2013, Houston signed future American League MVP Jose Altuve to a four-year, $17 million contract that turned out to be one of the game's biggest bargains. Singleton struggled (.620 OPS over 362 plate appearances) in his first callup, however, and has not appeared with the Astros since 2015.

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

Moore's extension -- a $14 million deal over five seasons -- was a first for pitchers, 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 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 2016 Deadline.

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

Smart analytical decisions transformed the Rays 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 his name on the dotted line. 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's extension was quickly seen as baseball's best contract in terms of the value it gave to the Rays, but he eventually got his proper value with another six-year, $100 million extension in 2012.

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.

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. But 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. Luckily for Anderson and the White Sox, there's still plenty of time for him to turn things around.

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

Cody Bellinger's 39-homer season partly overshadowed DeJong, who placed 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 that just topped Anderson's record deal.

"We talk a lot about the Cardinal Way and the character that we look at," said Cardinals vice president of baseball operations John Mozeliak, "and Paul exemplifies all of that."

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 2008) and then the Rays (for Matt Garza in 2011). Archer found his footing when he rejoined the Rays in June 2013, finishing third in the AL Rookie of the Year vote after going 9-7 with a 3.22 ERA in 23 starts.

Ryan Braun, Brewers -- May 2008 (One year and eight days of service time)

Braun exploded onto the scene in 2007, crushing 34 home runs and slugging a league-best .634 to just edge Troy Tulowitzki for NL Rookie of the Year honors. That was enough to convince the Brewers to give Braun a huge eight-year, $45 million extension, which at the time marked the biggest contract in franchise history. Braun's deal was the standard for an extension given to a player with under two seasons of service time for a number of years, and he certainly didn't rest on his laurels once the ink dried. The left fielder went on to claim five straight Silver Slugger Awards along with the NL MVP in 2011.

Troy Tulowitzki, Rockies -- January 2008 (One year and 33 days of service time)

Braun's deal followed in the footsteps of Tulo's six-year, $31 million extension, taking some of the sting off the Rockies' World Series defeat to the Red Sox months before. Rockies fans were certainly glad to see Tulowitzki remain in Denver, as the shortstop posted three top-10 finishes in MVP voting and a pair of Gold Glove and Silver Slugger Awards over the next four seasons. Tulowitzki signed a much bigger extension -- seven years and $134 million -- after the 2010 season before the Rockies eventually dealt him to the Blue Jays at the 2015 Deadline.

Anthony Rizzo, Cubs -- May 2013 (One year and 40 days of service time)

Rizzo was a highly touted prospect with the Red Sox, but he did not immediately deliver on that hype after he was dealt to the Padres as part of the Adrian Gonzalez trade in 2010. Rizzo found his footing with the Cubs in '12 (.805 OPS and 15 home runs over 87 games), and a hot start to the following season convinced Chicago to make him a face of the franchise with a seven-year, $41 million extension.

"To take a little bit of a discount now, but it's security for now [too]," Rizzo said at a news conference for the deal, "and a huge weight off my shoulders, my family's shoulders, my kids' shoulders, my grandkids' shoulders. It's a good feeling."

As it turns out, the good feelings were only beginning for Rizzo and the Cubs. The first baseman became a Chicago icon and perennial NL MVP candidate, leading the moribund Cubs from the NL cellar to their first World Series championship in 108 years in 2016.

Paul Goldschmidt, D-backs -- March 2013 (One year and 59 days of service time)

After a successful taste of the big leagues in 2011, Goldschmidt grabbed Arizona's first-base job for good by hitting 20 home runs and recording an .850 OPS over 145 games. That was enough for the D-backs to reward Goldschmidt with a five-year extension worth $32 million, and the best was yet to come. Spurred by his new contract, Goldschmidt took in a Gold Glove, Silver Slugger and a second-place finish in the NL MVP vote in '13 after leading the Senior Circuit with 36 homers, 125 RBIs and a .952 OPS. He remained a face of the D-backs franchise and a perennial MVP frontrunner until he was traded to the Cardinals in December 2018, before the final year of the deal.

Christian Yelich, Marlins -- March 2015 (One year and 69 days of service time)

The 23-year-old Yelich was seen as a superstar in the making, and the Marlins invested in his future with a seven-year, $49.5 million extension in 2015. Yelich's power was still blossoming at the time, but he grew into a 20-homer player while retaining his excellent average and eye at the plate. His extension would likely have continued to be a bargain for the Marlins down the road, but the franchise traded Yelich to the Brewers in January 2018 as part of their rebuilding effort.

Andrelton Simmons, Braves -- February 2014 (One year and 125 days of service time)

Simmons' glove at shortstop was already renowned leaguewide when he signed a seven-year, $58 million extension that remains a record for any player with less than two years of service time. Simmons remained inked under that extension once he was traded to the Angels, and it proved to be even more team-friendly for Los Angeles once he matured into a better all-around hitter.

Madison Bumgarner, Giants -- April 2012 (One year and 127 days of service time)

Bumgarner was already on his way toward becoming one of the league's preeminent aces, having won two postseason games as a 20-year-old for the World Series champion Giants in 2010 and recording a 3.21 ERA over 204 2/3 innings in 2011, his first full season in the rotation. The southpaw only got better after signing a five-year, $35 million extension, leading San Francisco to two more titles and compiling arguably the most heroic pitching performance in postseason history in 2014. Bumgarner ranked as one of baseball's biggest bargains through the length of this extension, remarkably ranking as the Giants' lowest-paid starter during the '16 season.

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