Aaron Judge and the Best Contract Years in MLB History

Joel ReuterSeptember 16, 2022

Aaron Judge and the Best Contract Years in MLB History

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    NEW YORK, NEW YORK - JUNE 29: Aaron Judge #99 of the New York Yankees in action against the Oakland Athletics at Yankee Stadium on June 29, 2022 in New York City. New York Yankees defeated the Oakland Athletics 5-3. (Photo by Mike Stobe/Getty Images)
    Aaron Judge (Mike Stobe/Getty Images)

    New York Yankees superstar Aaron Judge is putting the finishing touches on one of the most impressive contract years in baseball history, and a massive payday awaits this offseason as he tests the free-agent waters for the first time in his career.

    That got us to thinking about some of the other all-time great contract years.

    Remember Carlos Beltrán's electrifying 2004 postseason as a rental for the Houston Astros?

    Or Greg Maddux winning National League Cy Young honors in his final season with the Chicago Cubs before the same offseason when NL MVP Barry Bonds jumped ship from Pittsburgh to San Francisco?

    We've highlighted some of the greatest contract years in MLB history, ordered alphabetically. Let's kick things off with some honorable mentions.


    Hat tip to @AKIFFEL for suggesting this story idea to me on Twitter.

Honorable Mentions

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    HOUSTON, TX - SEPTEMBER 29:  Randy Johnson of the Houston Astros pitches during Game One of the National League Division Series against the San Diego Padres on September 29, 1998 at the Astrodome in Houston, Texas. (Photo by Sporting News via Getty Images via Getty Images)
    Randy Johnson (Sporting News via Getty Images via Getty Images)

    These players didn't make our list, but their contract years are worthy of a mention:

    • RP Rich Gossage, PIT (1977)
    • SP Nolan Ryan, CAL (1979)
    • OF Robin Yount, MIL (1989)
    • OF Bobby Bonilla, PIT (1991)
    • 1B Rafael Palmeiro, TEX (1993)
    • OF Larry Walker, MON (1994)
    • SP David Cone, TOR/NYY (1995)
    • OF Albert Belle, CLE (1996)
    • SP Randy Johnson, SEA/HOU (1998)
    • OF Bernie Williams, NYY (1998)
    • 2B Bret Boone, SEA (2001)
    • OF Gary Sheffield, ATL (2003)
    • C Ivan Rodriguez, FLA (2003)
    • OF J.D. Drew, ATL (2004)
    • OF Gary Matthews Jr., TEX (2006)
    • 3B Alex Rodriguez, NYY (2007)
    • OF Manny Ramirez, BOS/LAD (2008)
    • IF/OF Chone Figgins, LAA (2009)
    • 1B Prince Fielder, MIL (2011)
    • OF Josh Hamilton, LAA (2012)
    • SP Max Scherzer, DET (2014)
    • SP Jon Lester, BOS/OAK (2014)
    • SP David Price, DET/TOR (2015)
    • DH J.D. Martinez, DET/ARI (2017)
    • SP Gerrit Cole, HOU (2019)
    • 2B DJ LeMahieu, NYY (2020)
    • 2B Marcus Semien, TOR (2021)
    • 1B Freddie Freeman, ATL (2021)

CF Carlos Beltrán, 2004

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    HOUSTON - OCTOBER 16:  Carlos Beltran #15 of the Houston Astros smiles in the dugout after hitting a solo home run in eighth inning of Game 3 of National League Championship Series against the St. Louis Cardinals during the 2004 Major League Baseball Playoffs on October 16, 2004 at Minute Maid Park in Houston, Texas.  (Photo By Ronald Martinez/Getty Images)
    Photo By Ronald Martinez/Getty Images

    The American League Rookie of the Year for the Kansas City Royals in 1999, Carlos Beltrán became the best player on a thin roster, logging three straight 20-homer, 30-steal seasons heading into his contract year in 2004.

    Without the financial flexibility to sign him long-term, the Royals sold high on their star center fielder in June, shipping him to the Houston Astros in a three-team, five-player blockbuster deal that brought John Buck, Mark Teahen and Mike Wood to Kansas City.

    Beltrán didn't miss a beat while changing teams, finishing the '04 season with a 133 OPS+ while tallying 36 doubles, 38 home runs, 104 RBI, 121 runs scored and 42 steals in 45 attempts for a 6.8-WAR season.

    He then helped the Astros reach the NL Championship Series with one of the most impressive postseasons in MLB history, hitting .435/.536/1.022 with 20 hits, eight home runs and six steals in 12 games.

    The New York Mets signed him to a seven-year, $119 million deal that offseason.

3B Adrián Beltré, 2004

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    ST. LOUIS - SEPTEMBER 5:  Infielder Adrian Beltre #29 of the Los Angeles Dodgers bats during the game against the St. Louis Cardinals on September 5, 2004 at Busch Stadium in St. Louis, Mo. The Cardinals beat the Dodgers 6-5. (Photo by Dilip Vishwanat/Getty Images)
    Dilip Vishwanat/Getty Images

    Adrián Beltré made his MLB debut shortly after his 19th birthday, which meant he was just 25 years old when he reached his contract year with the Los Angeles Dodgers.

    A .262/.320/.428 hitter with a 97 OPS+ over the first six years of his career, Beltré exploded for a .334/.388/.629 line with an MLB-leading 48 home runs and 121 RBI in a 9.6-WAR season to send his free-agency stock skyrocketing.

    The Seattle Mariners signed him to a five-year, $64 million deal expecting him to be a franchise cornerstone, but he regressed to his previous level of production.

    Over the life of that five-year deal, he hit .266/.317/.442 for a 101 OPS+ while taking home a pair of Gold Glove Awards. It was not until his one-year deal with the Boston Red Sox in 2010 and his time with the Texas Rangers afterward that he found consistent, high-level production.

LF Barry Bonds, 1992

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    Baseball: Pittsburgh Pirates Barry Bonds (24) in action, at bat vs Chicago Cubs. Chicago, IL 4/24/1992 CREDIT: John Iacono (Photo by John Iacono /Sports Illustrated via Getty Images) (Set Number: X42797 )
    Set Number: X42797

    It's easy to forget that Barry Bonds was a two-time NL MVP winner before he even joined the San Francisco Giants, and one of those MVP wins came during his final season with the Pittsburgh Pirates in 1992.

    The 27-year-old hit .311/.456/.624 for a 204 OPS+ while tallying 36 doubles, 34 home runs, 103 RBI, 109 runs scored and 39 steals in a 9.0-WAR season for a Pirates team that won 96 games and the NL East title.

    One of the best players to reach free agency in the prime of his career, Bonds signed a six-year, $43.75 million deal with the Giants that was the largest contract in MLB history at the time. He immediately made good on the investment, repeating as NL MVP in 1993.

    The signing is often credited with saving baseball in San Francisco.

SP Kevin Brown, 1998

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    Pitcher Kevin Brown of the San Diego Padres delivers a pitch to the plate against the New York Yankees in the first inning of game four of the World Series 21 October at Qualcomm Stadium in San Diego, CA.  The Yankees lead in the best-of-seven series 3-0. (ELECTRONIC IMAGE)   AFP PHOTO  Timothy A. CLARY (Photo by Timothy A. CLARY / AFP) (Photo by TIMOTHY A. CLARY/AFP via Getty Images)
    TIMOTHY A. CLARY/AFP via Getty Images

    Right-hander Kevin Brown signed a three-year, $12.6 million deal with the Florida Marlins prior to the 1996 season. Over the life of that contract, he was arguably the best pitcher in baseball.

    1996: 32 GS, 17-11, 1.89 ERA, 0.94 WHIP, 159 K, 233.0 IP, 7.9 WAR
    1997: 33 GS, 16-8, 2.69 ERA, 1.18 WHIP, 205 K, 237.1 IP, 7.0 WAR
    1998: 35 GS, 18-7, 2.38 ERA, 1.07 WHIP, 257 K, 257.0 IP, 8.6 WAR

    He was the staff ace for the Marlins team that won the World Series in 1997. After they traded him to San Diego that offseason for a three-player package headlined by Derrek Lee, he helped lead the Padres to the World Series as well.

    That stellar three-year run, which culminated with the best season of his career in 1998, earned him baseball's first $100 million contract as he inked a seven-year, $105 million deal with the Los Angeles Dodgers.

1B Jason Giambi, 2001

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    24 Jun 2001:  Jason Giambi #16 of the Oakland Athletics at bat during the game against the Texas Rangers at the Network Associates Coliseum in Oakland, California. The Rangers defeated the Athletics 9-5.Mandatory Credit: Tom Hauck  /Allsport
    Tom Hauck

    Slugger Jason Giambi won AL MVP honors in 2000, but he arguably had an even better year the following season.

    2000: 187 OPS+, .333/.476/.647, 43 HR, 137 RBI, 7.8 WAR
    2001: 199 OPS+, .342/.477/.660, 38 HR, 120 RBI, 9.2 WAR

    As has so often been the case with Oakland Athletics stars, the tight-fisted club couldn't keep him around once free agency came calling, and he walked following the 2001 season.

    The New York Yankees signed him to a seven-year, $120 million deal. He racked up 440 home runs and 1,441 RBI in his 20-year MLB career.

SP Zack Greinke, 2015

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    LOS ANGELES, CA - OCTOBER 15:  Zack Greinke #21 of the Los Angeles Dodgers pitches in the first inning against the New York Mets in game five of the National League Division Series at Dodger Stadium on October 15, 2015 in Los Angeles, California.  (Photo by Sean M. Haffey/Getty Images)
    Sean M. Haffey/Getty Images

    After splitting the 2012 season between the Milwaukee Brewers and Los Angeles Angels, right-hander Zack Greinke signed a six-year, $147 million deal with the Los Angeles Dodgers, but the contract contained an opt-out after the 2015 season.

    In his opt-out year, he went 19-3 with a 1.66 ERA, 0.84 WHIP and 200 strikeouts in 222.2 innings, and his 222 ERA+ stands as one of the best single-season marks in MLB history. Despite that, he finished runner-up to Jake Arrieta in NL Cy Young voting after the Chicago Cubs ace put together a historically good second half.

    His stellar 2015 season made opting out a no-brainer, and he signed a six-year, $206.5 million deal with the Arizona Diamondbacks that set a record for average annual value.

OF Aaron Judge, 2022

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    NEW YORK, NY - SEPTEMBER 07: Aaron Judge (99) of the New York Yankees bats and hits a home run against the Minnesota Twins on September 2, 2022 at Yankee Stadium in New York, New York. (Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images)
    Brace Hemmelgarn/Minnesota Twins/Getty Images

    How many home runs will Aaron Judge hit?

    With two more long balls Tuesday, Judge has 57 home runs through the New York Yankees' 143 games this year, putting him on pace for a franchise-record 64 homers this season.

    He is also hitting .310/.413/.688 for an MLB-leading 208 OPS+, and he leads the AL in RBI (123), runs scored (117), walks (89) and WAR (9.1). Just as important is the fact that he has stayed healthy for the second straight year, and a career-high 73 games in center field should be a boon to his free-agency appeal.

    The 30-year-old bet on himself when he turned down a seven-year, $213.5 million extension offer before Opening Day, and he stands to take home an even more lucrative payday this offseason.

SP Greg Maddux, 1992

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    CHICAGO - 1992:  Greg Maddux of the Chicago Cubs pitches during an MLB game at Wrigley Field in Chicago, Illinois during the 1992 season. (Photo by Ron Vesely/MLB Photos via Getty Images)
    Ron Vesely/MLB Photos via Getty Images

    Hall of Famer Greg Maddux is best known for his time in an Atlanta Braves uniform, but his run of four NL Cy Young Awards in four years began with the Chicago Cubs in 1992.

    The 26-year-old went 20-11 with a 2.18 ERA, 1.01 WHIP and 199 strikeouts in 268 innings in his final season with the North Siders, tallying nine complete games and four shutouts on a team that finished with a sub-.500 record.

    Rather than give him a massive extension, the Cubs spread that money around on a few free-agent signings that didn't pan out, while Maddux went on to establish himself as one of the greatest pitchers in MLB history.

    He inked a five-year, $28 million deal with the Braves following the '92 season, turning down more money from the Yankees.

LF Manny Ramirez, 2000

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    CLEVELAND, OH - OCTOBER 7:  Manny Ramirez of the Cleveland Indidans bats during Game Two of the American League Division Series against the Boston Red Sox on October 7, 1999 at the Jacobs Field in Cleveland, Ohio. (Photo by Sporting News via Getty Images via Getty Images)
    Sporting News via Getty Images via Getty Images

    The 2000-01 MLB offseason saw two of baseball's most prolific offensive players change teams. While Alex Rodriguez secured a record-setting payday, Manny Ramirez was coming off an equally impressive contract year.

    Part of a stacked Cleveland offense that was among the best in baseball throughout the 1990s, Ramirez hit .351/.457/.697 for a 186 OPS+ with 34 doubles, 38 home runs and 122 RBI in just 118 games in 2000. He finished sixth in AL MVP voting and won the second of eight straight Silver Slugger Awards.

    Less than 24 hours after Rodriguez signed a record-shattering deal with the Texas Rangers, Ramirez agreed to an eight-year, $160 million contract with the Boston Red Sox at one of the wilder winter meetings in recent memory.

    The final offer from Cleveland was eight years and $136 million. How different things might have been if it had been willing to top Boston's offer.

3B Anthony Rendon and SP Stephen Strasburg, 2019

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    HOUSTON, TEXAS - OCTOBER 30:  Anthony Rendon #6 of the Washington Nationals hits a solo home run against the Houston Astros during the seventh inning in Game Seven of the 2019 World Series at Minute Maid Park on October 30, 2019 in Houston, Texas. (Photo by Tim Warner/Getty Images)
    Tim Warner/Getty Images

    The 2019 Washington Nationals went 19-31 through their first 50 games but rallied to claim a wild-card berth and eventually a World Series title.

    Third baseman Anthony Rendon led the way offensively, hitting .319/.412/.598 for a 157 OPS+ with 44 doubles, 34 home runs and 126 RBI, good for a team-leading 7.1 WAR in the best season of his career.

    On the mound, Stephen Strasburg went 18-6 with a 3.32 ERA, 1.04 WHIP and 251 strikeouts in 209 innings to finish fifth in NL Cy Young voting. He then went 5-0 with a 1.98 ERA, 0.94 WHIP and 47 strikeouts in 36.1 innings during the playoffs, taking home World Series MVP honors.

    The pair signed matching seven-year, $245 million contracts in free agency. Strasburg re-upped with the Nationals, and Rendon joined the Los Angeles Angels.

SS Alex Rodriguez, 2000

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    NEW YORK - CIRCA 1996: Alex Rodriguez #3 of the Seattle Mariners bats against the New York Yankees during an Major League Baseball game circa 1996 at Yankee Stadium in the Bronx borough of New York City. Rodriguez played for the Mariners from 1994-2000. (Photo by Focus on Sport/Getty Images)
    Focus on Sport/Getty Images

    Alex Rodriguez was just 25 years old when he reached free agency for the first time following the 2000 season, but he already had a 138 OPS+ with 189 home runs, 133 steals and 38.1 WAR in seven seasons with the Seattle Mariners.

    In 2000, he hit .316/.420/.606 with 34 doubles, 41 home runs, 132 RBI and 134 runs scored, racking up a career-high 10.4 WAR while providing stellar defense at shortstop and swiping 15 bases in 19 attempts.

    His age and elite production made a record-breaking contract a certainty. He signed a 10-year, $252 million deal with the Texas Rangers that was the largest in pro sports, shattering the six-year, $126 million contract that Kevin Garnett had signed with the Minnesota Timberwolves.

    He lasted just three seasons in Texas before the Rangers traded him to the New York Yankees, and he exercised an opt-out in the deal after seven seasons to sign a new 10-year, $275 million deal with the Yankees.

SP CC Sabathia, 2008

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    PHILADELPHIA - OCTOBER 02:  CC Sabathia #52 of the Milwaukee Brewers delivers in Game 2 of the NLDS Playoff against the Philadelphia Phillies  at Citizens Bank Ballpark on October 2, 2008 in Philadelphia, Pennsylvania  (Photo by Jeff Zelevansky/Getty Images)
    Jeff Zelevansky/Getty Images

    The reigning AL Cy Young winner heading into the final season of a two-year, $17.75 million extension in 2008, CC Sabathia became the most sought-after rental arm to hit the trade block since Randy Johnson when Cleveland made him available that summer.

    A contending Milwaukee Brewers team went all-in pursuing its first postseason berth since 1982, trading top prospect Matt LaPorta for Sabathia that July as part of a four-player package that also included a young Michael Brantley.

    Sabathia started 17 games over the final three months, often working on short rest, and he went 11-2 with a 1.65 ERA, 1.00 WHIP and 128 strikeouts in 130.2 innings, twirling seven complete games and three shutouts.

    That helped the Brewers edge the New York Mets by one game for the NL wild card. While the Philadelphia Phillies ousted Milwaukee in the NLDS, the season brought winning baseball back to a long-suffering franchise.

    Sabathia signed a seven-year, $161 million deal with the New York Yankees in free agency, but his three-month stint in Milwaukee will forever have a place in franchise lore.

LF Alfonso Soriano, 2006

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    ATLANTA - MAY 14: Alfonso Soriano #12 of the Washington Nationals hits against the Atlanta Braves at Turner Field on May 14, 2006 in Atlanta, Georgia. The Nationals defeated the Braves 8-1. (Photo by Scott Cunningham/Getty Images)
    Scott Cunningham/Getty Images

    Blink and you might have missed Alfonso Soriano's one-year stint with the Washington Nationals prior to reaching free agency for the first time in his career.

    The centerpiece of the deal that sent Alex Rodriguez from the Texas Rangers to the New York Yankees, Soriano spent two seasons with the Rangers before he was traded again, this time going to the Nats in exchange for Brad Wilkerson, Terrmel Sledge and Armando Galarraga.

    While the Nationals went 71-91 in 2006, Soriano was one of baseball's most electrifying players, hitting .277/.351/.560 with 41 doubles, 46 home runs and 41 steals to become the fourth player in MLB history to join the 40/40 club.

    The Chicago Cubs gave him an eight-year, $136 million deal in free agency that winter.

SP Rick Sutcliffe, 1984

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    Rick Sutcliffe of the Chicago Cubs on August 7,1984 at Wrigley Field in Chicago, Il. (Photo by Paul Natkin/Getty Images)
    Paul Natkin/Getty Images

    Rick Sutcliffe enjoyed some early success in the big leagues, winning NL Rookie of the Year in 1979 and claiming the AL ERA title three years later in his first season in Cleveland when he finished 14-8 with a 2.96 ERA in 216 innings.

    However, he went 4-5 with a 5.15 ERA and 1.66 WHIP in 94.1 innings to begin the 1984 season, and Cleveland dealt him to the Chicago Cubs in June in a seven-player deal that sent a young Joe Carter the other way.

    A switch flipped after he joined the Cubs, and he went 16-1 with a 2.69 ERA, 1.08 WHIP and 155 strikeouts in 150.1 innings to lead the Cubs to their first playoff berth since 1945. He also became the only pitcher to win Cy Young in a season when he was traded.

    The Cubs re-signed him to a five-year, $9.5 million deal that offseason to make him one of the highest-paid players in baseball.

1B Jim Thome, 2002

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    UNITED STATES - JULY 31:  Baseball: Closeup of Cleveland Indians Jim Thome during game vs Oakland Athletics, Oakland, CA 7/31/2002  (Photo by Brad Mangin/Sports Illustrated via Getty Images)  (SetNumber: X66449 TK1 R13 F5)
    Brad Mangin/Sports Illustrated via Getty Images

    Jim Thome slugged 612 home runs during his Hall of Fame career.

    He hit a career-high 52 of thosejim long balls during his contract year in 2002 when he was one of the few holdovers from the prolific Cleveland offenses of the 1990s.

    Aside from the gaudy home run total, he hit .304/.445/.677 for a 197 OPS+ while adding 118 RBI, 101 runs scored and 122 walks in a 7.4-WAR season that was among the best of his legendary career.

    After Cleveland finished 74-88 in 2002, the front office opted to clear a path for Ben Broussard at first base, and Thome landed with the Philadelphia Phillies on a six-year, $87.5 million deal.


    All stats courtesy of Baseball Reference, while contract information comes via various news articles.

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