Top 3 Best Free-Agent Signings in the History of Each MLB Franchise

Joel Reuter@JoelReuterBRFeatured ColumnistDecember 9, 2019

Top 3 Best Free-Agent Signings in the History of Each MLB Franchise

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    DAN LEVINE/Getty Images

    A few weeks ago, we took an in-depth look at the three worst free agent signings in the history of each MLB franchise.

    It was a dark and gloomy stroll down memory lane to say the least.

    Now it's time for the other, sunnier side of the spectrum, and a look at the best of the best when it comes to each MLB franchise's free agency history.

    With so many contracts to consider, the first step was to narrow the field by setting some parameters for inclusion. Those were as follows:

    • No contract extensions: Contract extensions and players re-signing with the same team in free agency were not considered for inclusion.
    • No one-year deals: Signing someone to a one-year contract is a no-risk move, so ranking them alongside multiyear deals doesn't seem fair.

    To help provide some better context, alongside each player's contract information is a multiplier to show how his salary stacked up to the league-average figure over the course of the deal.

    Now that we're on the same page, let's get started.

Arizona Diamondbacks

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    Randy Johnson
    Randy JohnsonMIKE FIALA/Getty Images

    No. 1: SP Randy Johnson—Dec. 10, 1998

    Terms: Five years, $68.4 million (6.6x league avg)

    The "Big Unit" was utterly dominant over the first four seasons of this contract, posting a 2.48 ERA and 1.04 WHIP while averaging 354 strikeouts and 258 innings. He won four straight NL Cy Young Awards and led the D-backs to a title in 2001. Knee surgery limited him to just 18 starts and a 4.26 ERA in the final year of the deal, but it still ranks as one of the best free-agent signings of all time.

          

    No. 2: OF Steve Finley—Dec. 18, 1998

    Terms: Four years, $21.5 million (2.7x league avg)

    Compelled to sign with the D-backs by the Johnson addition, Finley filled a hole in center field and immediately became one of the team's most productive offensive players. He hit .276/.351/.502 for a 111 OPS+ while averaging 27 home runs, 90 RBI and 3.3 WAR during his first four seasons in the desert. He also took home a pair of Gold Glove awards.

              

    No. 3: 2B/SS Jay Bell—Nov. 17, 1997

    Terms: Five years, $34 million (3.6x league avg)

    The day before the 1997 expansion draft, Bell officially became the first member of the D-backs organization. He exploded for a career year offensively in his age-33 season in 1999, posting a 131 OPS+ with 38 home runs and 112 RBI. He remained a productive player through the 2001 season, though his role during the team's playoff run was limited.

Atlanta Braves

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    Greg Maddux
    Greg MadduxTIMOTHY A. CLARY/Getty Images

    No. 1: SP Greg Maddux—Dec. 9, 1992

    Terms: Five years, $28 million (4.8x league avg)

    A strong case can be made that this is the greatest free-agent signing in MLB history. After winning his first Cy Young Award with the Chicago Cubs in 1992, Maddux added three more to his trophy case in '93, '94 and '95 and he won a World Series title in '95. Over the life of his initial five-year pact, he went 89-33 with a 2.13 ERA (197 ERA+), 0.96 WHIP and 39.0 WAR.

               

    No. 2: 3B Terry Pendleton—Dec. 3, 1990

    Terms: Four years, $10.2 million (2.5x league avg)

    The Braves took a real chance signing Pendelton to a lucrative four-year deal after he posted a disappointing 65 OPS+ with the St. Louis Cardinals in 1990. In his first season with the team, the Braves reached the World Series for the first time since 1958 and Pendleton took home NL MVP honors. He won the batting title (.319 BA) while posting a 139 OPS+ with 34 doubles, 22 home runs and 86 RBI. His production dipped over the final two years of the contract, but his role in launching the Braves run as perennial contenders earns him the No. 2 spot.

                

    No. 3: OF Brian Jordan—Nov. 23, 1998

    Terms: Five years, $40 million (3.9x league avg)

    A two-sport standout who spent two years as a starting safety for the Atlanta Falcons, Jordan took his baseball talents to Atlanta in 1999 after seven seasons with the St. Louis Cardinals. He averaged 22 home runs, 96 RBI and 3.3 WAR in his three seasons with the Braves, before he was traded to the Los Angeles Dodgers for slugger Gary Sheffield.

Baltimore Orioles

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    Rafael Palmeiro
    Rafael PalmeiroVincent Laforet/Getty Images

    No. 1: 1B Rafael Palmeiro—Dec. 12, 1993

    Terms: Five years, $30 million (4.9x league avg)

    After the strike-shortened 1994 season, Palmeiro averaged 40 home runs and 119 RBI over the final four years of his five-year pact with the Orioles. He showed up on AL MVP ballots in each of his five seasons in Baltimore, racking up 182 home runs and 23.4 WAR before rejoining the Texas Rangers at the end of the deal.

          

    No. 2: 2B Roberto Alomar—Dec. 21, 1995

    Terms: Three years, $18 million (4.7x league avg)

    Alomar was the American League's starting second baseman in the All-Star Game in each of his three seasons with the O's. The team reached the ALCS twice during his brief tenure, and he posted a 122 OPS+ and 12.5 WAR while winning a pair of Gold Glove awards. His subsequent contract with the Cleveland Indians also earned a mention in this article.

          

    No. 3: SS Miguel Tejada—Dec. 8, 2003

    Terms: Six years, $72 million (4.4x league avg)

    Tejada led the AL with 150 RBI in his first year with the Orioles and he had a solid 124 OPS+ and 20.1 WAR in four seasons with the team before he was traded to the Astros for a package of five players headlined by MLB outfielder Luke Scott and prospects Troy Patton and Mike Constanzo. He was just a year removed from AL MVP honors at the time of the signing.

Boston Red Sox

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    Manny Ramirez
    Manny RamirezCharles Krupa/Associated Press

    No. 1: OF Manny Ramirez—Dec. 19, 2000

    Terms: Eight years, $160 million (8x league avg)

    This move completely transformed the Red Sox organization, and directly led to a pair of World Series titles. Ramirez hit an impressive .312/.411/.588 with 274 home runs and 868 RBI during his time in Boston, while also adding a .321/.422/.558 line with 11 home runs and 38 RBI in 43 postseason games. He was traded to the Los Angeles Dodgers in a three-team deal that brought back Jason Bay in the final year of his contract.

          

    No. 2: OF Johnny Damon—Dec. 21, 2001

    Terms: Four years, $31 million (3.3x league avg)

    A dynamic catalyst atop the lineup and a colorful personality in the clubhouse, Damon hit .295 with a .362 on-base percentage and was a two-time All-Star in his four years with the team. His 461 runs scored during that span trailed only Albert Pujols (517) and Alex Rodriguez (485). Then he skipped town and spent four season with the rival New York Yankees.

          

    No. 3: 3B Bill Mueller—Jan. 10, 2003

    Terms: Three years, $6.7 million (0.9x league avg)

    The decision to give Mueller a three-year contract was a bit of a head-scratcher at the time after he posted a middling 98 OPS+ and 1.7 WAR in 2002. It wound up being a stroke of genius. He won the AL batting title (.326 BA) in his first year with the team and delivered 10.1 WAR and a 119 OPS+ on the team's $6.7 million investment.

Chicago Cubs

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    Jon Lester
    Jon LesterDavid Banks/Getty Images

    No. 1: SP Jon Lester—Dec. 15, 2014

    Terms: Six years, $155 million (6.3x league avg)

    This signing gave the Cubs the bona fide ace they were lacking to complement a young position-player core. After a solid first season, Lester was brilliant during the team's title run in 2016. He posted a 2.44 ERA in 202.2 innings to finish second in NL Cy Young voting, and he was even better in October. He made five postseason starts and pitched three innings of relief in Game 7 of the World Series, logging a 2.02 ERA and 0.93 WHIP in 35.2 playoff innings.

          

    No. 2: 2B Ben Zobrist—Dec. 8, 2015

    Terms: Four years, $56 million (3.2x league avg)

    Zobrist was an integral part of the 2016 team as well, hitting .272/.386/.446 with 31 doubles, 18 home runs and 3.7 WAR to earn the third All-Star nod of his career. He went 10-for-28 with three extra-base hits to earn World Series MVP honors. He had a down season in 2017 and the 2019 campaign was essentially a lost year, but his 2016 performance alone is enough to earn him the No. 2 spot.

          

    No. 3: LF Moises Alou—Dec. 19, 2001

    Terms: Three years, $27 million (3.9x league avg)

    Looking for some protection for Sammy Sosa in the middle of the lineup, Alou joined the Cubs for his age-35 season with plenty left in the tank. He hit .283/.353/.484 for a 116 OPS+ during his time on the North Side, including one of the best seasons of his career in 2004 when he had a 132 OPS+ with 39 home runs, 106 RBI and 4.0 WAR.

Chicago White Sox

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    Carlton Fisk
    Carlton FiskRon Vesely/Getty Images

    No. 1: C Carlton Fisk—March 18, 1981

    Terms: Five years, $2.9 million (2x league avg)

    Fisk was already 33 years old when he joined the White Sox after an impressive 11-year run with the Red Sox. However, he went on to play 13 more seasons for the South Siders. Over the course of this initial five-year pact, he posted a 114 OPS+ while averaging 21 home runs and 3.0 WAR. He finished third in AL MVP voting in 1983 when he helped lead the White Sox to their first postseason berth since 1959.

          

    No. 2: OF Jermaine Dye—Dec. 9, 2004

    Terms: Three years, $16.5 million (2.1x league avg)

    After a disappointing run with the Oakland Athletics, Dye helped lead the White Sox to an unexpected title in his first season with the team. He slugged 31 home runs and took home World Series MVP honors in 2005. That was followed by a 2006 campaign where he posted the best numbers of his career with a 151 OPS+, 44 home runs and 120 RBI to finish fifth in AL MVP voting.

          

    No. 3: 1B Jose Abreu—Oct. 29, 2013

    Terms: Six years, $68 million (2.7x league avg)

    A veteran of 10 seasons in the Cuban National Series, Abreu took the league by storm as a 27-year-old rookie in 2014, hitting .317/.383/.581 for an AL-leading 173 OPS+ and 36 home runs to win AL Rookie of the Year honors and finish third in MVP voting. Over his first six seasons stateside, he's posted a 134 OPS+ and averaged 36 doubles, 30 home runs and 102 RBI.

Cincinnati Reds

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    Dave Parker
    Dave ParkerRon Vesely/Getty Images

    No. 1: OF Dave Parker—Dec. 7, 1983

    Terms: Two years, $2.07 million (3x league avg)

    After 11 seasons with the Pittsburgh Pirates, Parker took his impressive resume that included four All-Star Game appearances, a pair of NL batting titles and 1978 MVP honors to Cincinnati. After a modest first season, he slugged a career-high 34 home runs in 1985 while also leading the NL in doubles (42), RBI (125) and total bases (350) to finish second in MVP voting. He spent two more seasons with the Reds before moving on to Oakland.

          

    No. 2: RP Aroldis Chapman—Jan. 11, 2010

    Terms: Six years, $30.25 million (1.5x league avg)

    Chapman was something of an enigma when he first defected from Cuba, and the Reds initially tried to develop him as a starter. However, he quickly found a home at the back of the bullpen, and in six seasons with the team he racked up 146 saves with a 2.17 ERA, 1.02 WHIP and 15.4 K/9 in 324 appearances.

          

    No. 3: OF Ron Gant—June 21, 1994

    Terms: Two years, $3.633 million (1.6x league avg)

    The Reds signed Gant to a two-year contract midway through the 1994 season, despite the likelihood that he would not see the field that year. That was indeed the case, but he made good on the team's investment the following season when he hit .276/.386/.554 with 29 home runs and 23 steals to finish 11th in NL MVP voting and help the Reds to an NL Central title.

Cleveland Indians

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    Roberto Alomar
    Roberto AlomarJOHN ZICH/Getty Images

    No. 1: 2B Roberto Alomar—Dec. 1, 1998

    Terms: Four years, $32 million (4x league avg)

    The three years that Alomar spent in Cleveland go down as one of the most productive stretches in MLB history for a second baseman. He hit .323/.405/.515 for a 134 OPS+ while averaging 21 home runs, 103 RBI, 121 runs scored, 35 steals and 6.8 WAR. He was traded to the New York Mets ahead of the fourth and final year of his contract and his production promptly bottomed out.

          

    No. 2: OF Kenny Lofton—Dec. 8, 1997

    Terms: Four years, $30.6 million (4.3x league avg)

    Traded to the Atlanta Braves prior to the 1997 season in a blockbuster deal that brought David Justice and Marquis Grissom to Cleveland, Lofton returned to the Indians the following offseason. He was not quite the same dynamic offensive player he was during his first tour of duty with the club, but he still hit .280/.367/.416 with 125 steals and 16.8 WAR in his second go-around.

          

    No. 3: SP Orel Hershiser—April 8, 1995

    Terms: Three years, $6.35 million (1.8x league avg)

    This one was a toss-up between Hershiser and fellow veteran Dennis Martinez, who both pitched better than expected at the twilight of lengthy MLB careers. Superior durability and a strong 1995 postseason that included ALCS MVP honors ultimately earned Hershiser the nod. He went 45-21 with a 4.21 ERA (113 ERA+) while averaging 30 starts and 190 innings during his time in Cleveland.

Colorado Rockies

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    Larry Walker
    Larry WalkerBrian Bahr/Getty Images

    No. 1: OF Larry Walker—April 8, 1995

    Terms: Four years, $22.5 million (4.5x league avg)

    Walker set career highs in home runs (36) and RBI (101) in his first season with the Rockies, and he was just getting started. Two years later, he hit .366/.452/.720 with 49 home runs, 130 RBI and 9.8 WAR to win NL MVP honors. That was followed by three NL batting titles in four years, though the final two were not part of this initial contract.

          

    No. 2: OF Ellis Burks—Nov. 16, 1992

    Terms: Three years, $10 million (3x league avg)

    While he played in just 145 games total over the first two years of his contract, Burks earns the No. 2 spot on the strength of his huge 1997 campaign. He hit .344/.408/.639 with 45 doubles, 40 home runs, 128 RBI, 142 runs scored and 32 steals for 7.9 WAR and a third-place finish in NL MVP voting.

          

    No. 3: OF Michael Cuddyer—Dec. 16, 2011

    Terms: Three years, $31.5 million (3.1x league avg)

    Cuddyer had a 102 OPS+ in his first year with the Rockies and played in just 49 games in the third year, but in between he won the NL batting title (.331 BA) and tallied 31 doubles, 20 home runs and 84 RBI to win Silver Slugger honors.

Detroit Tigers

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    Ivan Rodriguez
    Ivan RodriguezCARLOS OSORIO/Associated Press

    No. 1: C Ivan Rodriguez—Feb. 6, 2004

    Terms: Five years, $53 million (4x league avg)

    This signing represented a changing of the guard for a Tigers team that had suffered through 100-loss seasons in 2002 (55-106) and 2003 (43-119). They improved to 72 wins in Pudge's first year with the team, and by 2006 they were in the World Series. He made four All-Star teams, won three Gold Glove awards and tallied 14.2 WAR during his time in Detroit.

         

    No. 2: UT Tony Phillips—Dec. 5, 1989

    Terms: Five years, $10 million (2.1x league avg)

    One of the most underrated players in MLB history, Phillips played all over the field for the Tigers as one of the first true super-utility players. The on-base machine hit .281/.395/.405 for a 120 OPS+ with 502 runs scored and 25.3 WAR in his five seasons with the Tigers.

          

    No. 3: 3B Darrell Evans—Dec. 17, 1983

    Terms: Three years, $2.25 million (2x league avg)

    This was a tough call, with Victor Martinez receiving some serious consideration, but in the end Evans is the pick for the part he played in the team's 1984 World Series win. The 37-year-old was a 1.3 WAR player in '84, and he led the AL with 40 home runs the following season. All told, he socked 85 home runs and tallied 8.8 WAR in the first three years of what would be a five-year stint in Detroit.

Houston Astros

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    Nolan Ryan
    Nolan RyanRon Vesely/Getty Images

    No. 1: SP Nolan Ryan—Nov. 19, 1979

    Terms: Four years, $4.5 million (5.2x league avg)

    This contract made Nolan Ryan the first player in MLB history to earn more than $1 million in a season, and he proved to be more than deserving. He won an ERA title (1.69) during the strike-shortened 1981 season and tossed 24 complete games, 10 shutouts and one no-hitter during his first four seasons in Houston while posting a 2.91 ERA and 1.22 WHIP in 829.1 innings.

          

    No. 2: 2B Jeff Kent—Dec. 18, 2002

    Terms: Two years, $17.5 million (3.7x league avg)

    After a stellar tenure with the San Francisco Giants, Kent joined the Astros for a two-year run and briefly pushed Craig Biggio to the outfield. He hit .293/.350/.521 for a 121 OPS+ while averaging 36 doubles, 24 home runs, 100 RBI and 3.4 WAR before moving on and signing with the Los Angeles Dodgers.

          

    No. 3: SP Andy Pettitte—Dec. 16, 2003

    Terms: Three years, $31.5 million (4.2x league avg)

    While a series of one-year contracts for Roger Clemens dominated the headlines, Pettitte was an equally important part of the Astros success in the mid-2000s. The longtime Yankee had arguably the best season of his career in 2005 when Houston reached the World Series, going 17-9 with a 2.39 ERA (177 ERA+), 1.03 WHIP and 171 strikeouts in 222.1 innings to finish fifth in NL Cy Young voting.

Kansas City Royals

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    David Cone
    David ConeOwen C. Shaw/Getty Images

    No. 1: SP David Cone—Dec. 8, 1992

    Terms: Three years, $18 million (5.4x league avg)

    Given the chance to rectify the ill-advised decision to trade Cone to the New York Mets early in his career, owner Ewing Kauffman made him the highest-paid pitcher in baseball when he hit free agency, and the deal included a then-massive $9 million signing bonus. He was worth 7.2 WAR in his first season back in Kansas City and he won AL Cy Young honors during the strike-shortened '94 season, before he was traded again, this time to Toronto.

          

    No. 2: DH Kendrys Morales—Dec. 16, 2014

    Terms: Two years, $17 million (2.1x league avg)

    Morales struggled to stay healthy early in his career, but he was a staple in the Royals' lineup during his two seasons with the team, playing in 312 of 324 games. He led the 2015 World Series winning team in OPS+ (127) and RBI (102) and he tied for the team lead in home runs (22). That was followed by a career-high 30 home runs in 2016.

          

    No. 3: SP Edinson Volquez—Dec. 29, 2014

    Terms: Two years, $20 million (2.4x league avg)

    While his ERA spiked to 5.37 in the second year of the deal, Volquez was instrumental in bringing a title to Kansas City in 2015. He went 13-7 with a 3.04 ERA, 1.23 WHIP and 140 strikeouts in 192.2 innings during the regular season, then posted a 3.77 ERA in five appearances during the playoffs, including quality starts in Game 1 and Game 5 of the World Series.

Los Angeles Angels

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    Vladimir Guerrero
    Vladimir GuerreroStephen Dunn/Getty Images

    No. 1: OF Vladimir Guerrero—Jan. 14, 2004

    Terms: Six years, $85 million (5.2x league avg)

    If you're looking for an immediate return on investment, it doesn't get much better than this. After an eight-year run with the Montreal Expos, Guerrero hit .337/.391/.598 with 39 doubles, 39 home runs, 126 RBI and an AL-leading 124 runs scored to win AL MVP honors in his first season in an Angels uniform. Over the life of the contract, he posted a 141 OPS+ and averaged 29 home runs, 103 RBI and 3.8 WAR.

          

    No. 2: 2B Bobby Grich—Nov. 24, 1976

    Terms: Five years, $1.5 million (2.4x league avg)

    After a shaky first season with the Angels where he played in just 52 games and posted a disappointing 98 OPS+, Grich settled in as one of the most productive second baseman in baseball. Over the next three seasons, he put up a 140 OPS+ and averaged 22 doubles, 22 home runs, 75 RBI and 5.2 WAR. All told, he played 10 seasons with the Angels and he was the first player inducted into the team's Hall of Fame in 1988.

          

    No. 3: OF Torii Hunter—Nov. 22, 2007

    Terms: Five years, $90 million (5.9x league avg)

    The Angels paid a steep price to sign Hunter prior to the 2008 season and he had no problem living up to his salary. He hit .286/.352/.462 for a 122 OPS+ and averaged 21 home runs and 86 RBI, while also adding two more Gold Glove awards to his mantle. He was worth 20.7 WAR during his five seasons in an Angels uniform.

Los Angeles Dodgers

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    Kirk Gibson
    Kirk GibsonFocus On Sport/Getty Images

    No. 1: OF Kirk Gibson—Jan. 29, 1988

    Terms: Three years, $4.5 million (2.9x league avg)

    In his first season with the Dodgers, Gibson hit .290/.377/.483 for a 148 OPS+ with 25 home runs and 31 steals to claim NL MVP honors. He added two more long balls in the NLCS, before launching one of the most memorable home runs in MLB history off Dennis Eckersley in the World Series. Injuries limited him to just 160 games over the final two seasons, but his memorable '88 campaign is enough to land him the No. 1 spot.

          

    No. 2: SP Zack Greinke—Dec. 10, 2012

    Terms: Three years, $76 million (7x league avg)

    Originally a six-year, $147 million contract, Greinke opted out after three years to sign a new six-year, $206.5 million deal with the Diamondbacks. During his three-year stint with the Dodgers, he finished in the top 10 in NL Cy Young voting each year, posting a 2.30 ERA and 1.03 WHIP while averaging 201 innings and 5.9 WAR.

          

    No. 3: OF Brett Butler—Dec. 14, 1990

    Terms: Four years, $13 million (3.2x league avg)

    Even entering his mid-30s, Butler was still a dynamic speed threat atop the lineup. During his four seasons with the Dodgers, he hit .303 with a .402 on-base percentage, 145 steals and 15.2 WAR. The Dodgers signed Darryl Strawberry during the same offseason for significantly more money, but it was Butler who ended up being the more impactful addition.

Miami Marlins

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    Kevin Brown
    Kevin BrownRHONA WISE/Getty Images

    No. 1: SP Kevin Brown—Dec. 22, 1995

    Terms: Three years, $12.6 million (3.3x league avg)

    Brown immediately took his game to another level after joining the Marlins, leading the NL in ERA (1.89), ERA+ (215), and WHIP (0.94) in 1996 to finish second to John Smoltz in NL Cy Young voting. The following year, he served as the ace of the staff for a Marlins team that went on to win the World Series. He was shipped to the San Diego Padres in the subsequent fire sale in a deal that brought back first baseman Derrek Lee.

          

    No. 2: OF Moises Alou—Dec. 12, 1996

    Terms: Five years, $25 million (3x league avg)

    Alou spent just one season with the Marlins before he was traded, but it was a memorable one. He led the title-winning '97 team in home runs (23) and RBI (115) before he was flipped to the Houston Astros for a package of three players that did not amount to much at the MLB level.

          

    No. 3: SP Al Leiter—Dec. 14, 1995

    Terms: Three years, $8.6 million (2.2x league avg)

    Leiter joined the Marlins starting rotation in '96 as the No. 2 guy behind Brown, posting a 2.93 ERA with 200 strikeouts in 215.1 innings to earn his first All-Star nod and finish ninth in Cy Young balloting. He wasn't quite as sharp the following season, but he still posted a respectable 4.34 ERA over 27 starts. He too was moved in the fire sale, in a deal that brought back A.J. Burnett.

Milwaukee Brewers

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    Mike Cameron
    Mike CameronLisa Blumenfeld/Getty Images

    No. 1: OF Mike Cameron—Jan. 11, 2008

    Terms: Two years, $16.5 million (2.8x league avg)

    Despite joining the Brewers at the age of 35, Cameron still had plenty of power in the batter's box and he still moved like a gazelle in center field. In his two seasons with the team, he posted a 111 OPS+ and slugged 49 home runs, while posting 6.1 WAR largely on the strength of his glove work.

          

    No. 2: DH Dave Parker—Dec. 3, 1989

    Terms: Three years, $3 million (1.2x league avg)

    Still going strong entering his age-39 season, Parker hit .289/.330/.451 for a 118 OPS+ in 1990 with 30 doubles, 21 home runs and 92 RBI to earn a trip to the All-Star Game, Silver Slugger honors and a 16th-place finish in AL MVP voting. He was traded to the Angels after one year for outfielder Dante Bichette.

          

    No. 3: OF Lorenzo Cain—Jan. 26, 2018

    Terms: Five years, $80 million (3.3x league avg)

    Two years into this contract, it looks like a legitimate contender for the No. 1 spot on this list before all is said and done. In his first season with the Brew Crew, Cain hit .308/.395/.417 with 37 extra-base hits and 30 steals in a 6.9-WAR season. His offensive production dipped a bit in 2019, but he was still a 2.8-WAR player and he won his first Gold Glove.

Minnesota Twins

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    Chili Davis
    Chili DavisBob Galbraith/Associated Press

    No. 1: DH Chili Davis—Jan. 29, 1991

    Terms: Two years, $4.5 million (2.4x league avg)

    The Twins won the World Series in 1991, a year after finishing 74-88, and the addition of Davis was one of the biggest catalysts for their improvement. He led the title-winning team in OPS+ (141), on-base percentage (.385), doubles (34), home runs (29) and RBI (93). He also hit two home runs in the World Series. He had a 130 OPS+ and 12 home runs in a 2.0 WAR season the following year, before returning to the Angels.

          

    No. 2: DH Nelson Cruz—Jan. 2, 2019

    Terms: Two years, $26 million (3.2x league avg)

    Now that the Twins have exercised their 2020 option on Cruz, his contract can be considered a multi-year deal and is therefore eligible for inclusion on this list. Added to provide some punch in the middle of a young lineup, he did just that in 2019, hitting .311/.392/.639 with 41 home runs and 108 RBI in his age-38 season. He's showing no signs of slowing down, so another big season could be on tap for 2020.

          

    No. 3: DH Paul MolitorDec. 5, 1995

    Terms: Two years, $5.5 million (2.2x league avg)

    Molitor hit .341/.390/.468 and led the AL in hits (225) as a 39-year-old in his first season with the Twins, picking up his 3,000th career hit in the process. He remained productive over the final two years of the contract, hitting .293/.343/.410 for a 96 OPS+, before calling it a career.

New York Mets

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    Carlos Beltran
    Carlos BeltranAl Bello/Getty Images

    No. 1: OF Carlos Beltran—Jan. 13, 2005

    Terms: Seven years, $119 million (5.9x league avg)

    Keep in mind, Mike Piazza was acquired in a trade and then re-signed, so he was not eligible. With that said, Beltran is a clear choice for the top spot, despite the fact that the Mets reached the playoffs just once during his tenure. The dynamic power-speed threat made five All-Star teams and hit .280/.369/.500 for a 129 OPS+ with 149 home runs, 100 steals and 31.1 WAR. The team also managed to turn him into Zack Wheeler when he was flipped to the San Francisco Giants at the deadline in the final year of his contract.

          

    No. 2: 3B Robin Ventura—Dec. 1, 1998

    Terms: Four years, $32 million (4x league avg)

    Ventura hit .301/.379/.529 with 38 doubles, 32 home runs and 120 RBI while posting 6.2 WAR in his first season with the Mets, finally garnering some well-deserved national attention after being largely underrated during his time with the White Sox. He tallied 11.0 WAR overall in three seasons with the Mets, before he was traded to the Yankees for David Justice.

          

    No. 3: OF Curtis Granderson—Dec. 9, 2013

    Terms: Four years, $60 million (3.7x league avg)

    After four seasons with the Yankees, Granderson joined the Mets and waived goodbye to the short porch at Yankee Stadium that assisted in back-to-back 40-homer seasons in 2011 and 2012. While he was not as prolific a power hitter, he remained plenty productive following the move, averaging 28 doubles and 25 home runs while hitting .241/.342/.436 for a 116 OPS+ in the first three years of his contract. His time with the Mets was worth 11.0 WAR.

New York Yankees

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    Reggie Jackson
    Reggie JacksonMarty Lederhandler/Associated Press

    No. 1: OF Reggie Jackson—Nov. 29, 1976

    Terms: Five years, $2.9 million (4.7x league avg)

    One of the first true stars to change teams in free agency, Jackson was already a six-time All-Star with two World Series titles and an AL MVP award on his resume when he joined the Yankees. He posted a 148 OPS+ with 17.2 WAR and slugged 144 regular-season home runs while launching another 12 playoff long balls in 34 October games during his five seasons in the Bronx.

          

    No. 2: SP Mike Mussina—Dec. 7, 2000

    Terms: Six years, $87 million (6.1x league avg)

    The ace of the Orioles' staff for the better part of a decade, Mussina didn't miss a beat upon joining the Yankees for his age-32 season. He wound up spending the final eight seasons of his career in pinstripes, and over the course of his initial six-year deal, he went 92-53 with a 3.80 ERA (117 ERA+) and 1.18 WHIP en route to 29.1 WAR. The Yankees paid a premium price and he was worth every penny.

          

    No. 3: SP Orlando Hernandez—March 23, 1998

    Terms: Four years, $6.6 million (0.9x league avg)

    Guys like Dave Winfield, Hideki Matsui, Goose Gossage and Jimmy Key all received serious consideration for the No. 3 spot, but it's hard to argue with the overall success that "El Duque" enjoyed during his time with the Yankees. Signed as a 32-year-old wild card after he defected from Cuba, he quickly pitched his way into the rotation. While he was solid during the regular season, it was his October performance that earns him a place on this list. In 11 postseason appearances during the team's three straight World Series titles from 1998 to 2000, he went 8-1 with a 2.20 ERA, 1.18 WHIP and .194 opponents' batting average in 73.2 innings.

Oakland Athletics

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    Dave Henderson
    Dave HendersonFocus On Sport/Getty Images

    No. 1: OF Dave Henderson—Dec. 21, 1987

    Terms: Three years, $1.925 million (1.3x league avg)

    Truly one of the best bargain signings in MLB history, Henderson played in three straight World Series after signing with the Athletics. It may come as a surprise to learn that he led the team with 15.4 WAR during that span, ahead of the likes of Rickey Henderson (15.0), Jose Canseco (14.9), Dave Stewart (13.5) and Mark McGwire (12.0). Not bad for a guy making roughly the league average.

          

    No. 2: SP Mike Moore—Nov. 28, 1988

    Terms: Three years, $4 million (2.1x league avg)

    Signed to round out a rotation that already included Dave Stewart, Bob Welch, Storm Davis and Curt Young, Moore made an immediate impact in 1989, going 19-11 with a 2.61 ERA and 1.14 WHIP in 241.2 innings to finish third in AL Cy Young voting. He also went 3-0 with a 1.35 ERA in three starts that October to help Oakland to a World Series title. All told, he had a 3.35 ERA and 8.5 WAR during his first three seasons with the A's.

        

    No. 3: OF Yoenis Cespedes—Feb. 13, 2012

    Terms: Four years, $36 million (2.5x league avg)

    The addition of Cespedes represented a major financial roll of the dice for the typically frugal A's, and the risk paid off almost immediately. He hit .292/.356/.505 with 23 home runs to finish second in AL Rookie of the Year voting in 2012 and then slugged 26 home runs the following season, before he was traded to the Red Sox at the 2014 deadline in exchange for Jon Lester.

Philadelphia Phillies

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    Pete Rose
    Pete RoseBill Ingraham/Associated Press

    No. 1: 1B Pete Rose—Dec. 5, 1978

    Terms: Four years, $3.225 million (4.7x league avg)

    Prior to signing Rose, the Phillies had been ousted in the NLCS in three straight seasons. While they missed the playoffs in his first season with the team, he helped them finally get over the hump in 1980, bringing home the first World Series title in franchise history. He hit .300 with a .375 on-base percentage and made four All-Star teams in his first four seasons in Philly.

          

    No. 2: SP Cliff Lee—Dec. 15, 2010

    Terms: Five years, $120 million (7x league avg)

    The Phillies originally acquired Lee from the Indians at the 2009 trade deadline, only to flip him to Seattle during the subsequent offseason. However, he made his way back to Philadelphia when he reached free agency a year later, joining Roy Halladay, Cole Hamels and Roy Oswalt in a stacked rotation. He was one of the best pitchers in baseball during the first three-plus years of the deal, posting a 2.89 ERA and 1.09 WHIP in 106 starts, before shoulder issues effectively ended his career.

          

    No. 3: 1B Jim Thome—Dec. 6, 2002

    Terms: Six years, $85 million (5.4x league avg)

    Thome averaged 44 home runs and 118 RBI while hitting .270/.391/.576 for a 149 OPS+ during his first two seasons in Philadelphia, before an elbow injury limited him to 59 games in 2005. In his absence, Ryan Howard won NL Rookie of the Year and Thome became expendable. As a result, he was traded to the White Sox for Aaron Rowand and Gio Gonzalez prior to the 2006 season.

Pittsburgh Pirates

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    Russell Martin
    Russell MartinCharlie Neibergall/Associated Press

    No. 1: C Russell Martin—Nov. 30, 2012

    Terms: Two years, $17 million (2.4x league avg)

    A $17 million commitment might not seem like much, but for the small-market Pirates, it represented a significant free agency splurge. The franchise snapped a 20-year postseason drought in Martin's first year with the team, then returned to the playoffs again in 2014. He posted a 116 OPS+ while averaging 13 home runs and 61 RBI, also adding 40 DRS behind the plate for 9.4 WAR overall.

          

    No. 2: SP Francisco Liriano—Feb. 8, 2013

    Terms: Two years, $7 million (1x league avg)

    The first in a line of successful reclamation projects for pitching coach Ray Searage, Liriano had a 5.23 ERA over 291 innings in the two years prior to joining the Pirates. In his first season in Pittsburgh, he went 16-8 with a 3.02 ERA and 163 strikeouts in 161 innings to finish ninth in NL Cy Young voting. He had similar numbers the following year, earning himself a three-year, $39 million when he reached free agency again.

          

    No. 3: SP Jim Bibby—March 15, 1978

    Terms: Five years, $700,000 (0.9x league avg)

    It took some digging to find a third multi-year contract worthy of inclusion on this list. We're making some assumptions on the specifics of Bibby's contract, based on article from Rory Costello of SABR.org, so it might not be quite the bargain it appears. Regardless, Bibby pitched extremely well in a swingman role during his first four seasons in Pittsburgh. In 79 starts and 38 relief appearances during that span, he posted a 3.11 ERA, 1.21 WHIP and 9.6 WAR, finishing third in NL Cy Young voting in 1980.

San Diego Padres

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    Steve Garvey
    Steve GarveyOwen C. Shaw/Getty Images

    No. 1: 1B Steve Garvey—Dec. 21, 1982

    Terms: Five years, $6.6 million (3.6x league avg)

    The Padres spent big to sign a 34-year-old Garvey following a standout 14-year run with the Dodgers. While he was not the same MVP-level player he was in his prime, he was an impactful addition nonetheless. He led the 1984 team that reached the World Series in RBI (86), and his walk-off, two-run home run off Cubs closer Lee Smith in Game 4 of the NLCS that year stands as one of the biggest moments in franchise history.

          

    No. 2: RP Goose Gossage—Jan. 6, 1984

    Terms: Five years, $5.5 million (2.8x league avg)

    Also a key contributor to the 1984 pennant-winning team, Gossage worked 102.1 innings out of the San Diego bullpen that season, tallying 25 saves while posting a 2.90 ERA and 1.09 WHIP to finish fifth in Cy Young voting. He saved 83 games and posted 4.4 WAR in four seasons with the Padres before he was traded to the Cubs ahead of the final year of his contract.

          

    No. 3: C Gene Tenace—Dec. 14, 1976

    Terms: Six years, $2.475 million (2.9x league avg)

    The catcher for the Oakland teams that won three straight World Series titles during the 1970s, Tenace posted a 136 OPS+ with a .403 on-base percentage while averaging 17 home runs, 60 RBI and a 4.9 WAR in four seasons with the Padres before he was traded to the Cardinals in an 11-player blockbuster deal.

San Francisco Giants

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    Barry Bonds
    Barry BondsEric Risberg/Associated Press

    No. 1: OF Barry Bonds—Dec. 8, 1992

    Terms: Six years, $43 million (6x league avg)

    The largest deal in MLB history at the time, Bonds was already a two-time MVP when he left Pittsburgh and joined the Giants. He added another MVP in 1993 when he led the NL in home runs (46) and RBI (123) in a 9.9 WAR season. All told, he hit .307/.445/.617 for a 182 OPS+ with 235 home runs, 194 steals and 49.6 WAR during his first six seasons in San Francisco.

         

    No. 2: OF Brett Butler—Dec. 1, 1987

    Terms: Three years, $2.9 million (1.9x league avg)

    Prior to joining the rival Dodgers, Butler spent three seasons setting the table for the Giants lineup. He hit .293 with a .381 on-base percentage and 125 steals during his time with San Francisco, leading the NL in runs scored in '88 (109) and hits in '90 (192). He was the starting center fielder on the 1989 team that won the NL pennant, and he went 4-for-14 with two steals in the World Series.

        

    No. 3: RP Jeremy Affeldt—Nov. 17, 2008

    Terms: Two years, $8 million (1.3x league avg)

    Part of the "Core Four" of reliever that played such a vital role in the Giants run to three World Series titles in five yearsalong with Sergio Romo, Santiago Casilla and Javier Lopez—Affeldt spent time with the Royals, Rockies and Reds before landing in San Francisco. In his first year with the team, he posted a pristine 1.73 ERA with 33 holds in 74 appearances, and the following year he was a key piece of a World Series winner. He ended up spending seven seasons total with the Giants.

Seattle Mariners

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    Ichiro Suzuki
    Ichiro SuzukiDAN LEVINE/Getty Images

    No. 1: OF Ichiro Suzuki—Nov. 30, 2000

    Terms: Three years, $14.088 million (2.1x league avg)

    Despite a nine-year professional career in Japan that included a .353 career average and 1,278 hits, no one was quite sure how Ichiro's game would translate to the MLB level. Those questions were immediately answered when he led the AL in batting average (.350), hits (242) and steals (56) to win AL MVP honors as a rookie. He went on to hit .328/.374/.440 with 662 hits and 121 steals over his initial three-year deal.

          

    No. 2: DH Nelson Cruz—Dec. 4, 2014

    Terms: Four years, $57 million (3.3x league avg)

    After leading the AL with 40 home runs on a one-year deal with the Orioles in 2014, Cruz joined the Mariners on a four-year deal. During that span, he led the majors with 163 home runs, hitting .284/.362/.546 for a 148 OPS+ in the process. While WAR tends to devalue offense-only designated hitters, he was still worth 17.0 during his time in Seattle.

          

    No. 3: 1B John Olerud—Dec. 15, 1999

    Terms: Three years, $20 million (3.2x league avg)

    After trading Ken Griffey Jr. to the Reds, the Mariners set to work rebuilding the roster during the 1999-2000 offseason, which included signing Olerud to a three-year deal. He went on to hit .291/.399/.467 while averaging 19 home runs, 100 RBI and 4.7 WAR in his first three years with the team. He also won two Gold Gloves and earned a starting nod at the 2001 All-Star Game.

St. Louis Cardinals

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    Darrell Porter
    Darrell PorterFocus On Sport/Getty Images

    No. 1: C Darrell Porter—Dec. 7, 1980

    Terms: Five years, $3.5 million (2.5x league avg)

    The popular answer here might be Chris Carpenter, but he actually joined the Cardinals on a one-year, $300,000 deal, so he was not eligible for inclusion. That leaves us with Porter, who was tasked with filling the shoes of franchise icon Ted Simmons. He posted a 109 OPS+ and 11.7 WAR in his five seasons in St. Louis, and his defining moment came in the 1982 postseason when he won NLCS and World Series MVP honors.

          

    No. 2: SS David Eckstein—Dec. 23, 2004

    Terms: Three years, $10.25 million (1.3x league avg)

    Slim pickings on the free-agent market convinced the Cardinals to give Eckstein a three-year deal, despite a career 87 OPS+ at the time. He hit for a solid average (.297) with decent on-base numbers (.357) in St. Louis, though his lack of power limited him to a 91 OPS+. Still, he was worth 5.4 WAR in three seasons, and his postseason experience from his time with the Angels was evident in 2006 when he went 8-for-22 with three doubles in the Fall Classic to win World Series MVP honors.

          

    No. 3: RP Jason Isringhausen—Dec. 11, 2001

    Terms: Four years, $27 million (2.9x league avg)

    The franchise leader in saves (217), Isringhausen came to the Cardinals after the former Mets top prospect broke out in the closer's role in Oakland. He converted 140 of 159 save chances during his initial four-year deal, including an NL-leading 47 saves for the eventual NL pennant winners in 2004. Workhorse starter Jeff Suppan also received some consideration for the No. 3 spot.

Tampa Bay Rays

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    Fernando Rodney
    Fernando RodneyHannah Foslien/Getty Images

    No. 1: RP Fernando Rodney—Jan. 4, 2012

    Terms: Two years, $4.25 million (0.6x league avg)

    After flaming out in Detroit and then turning in a forgettable two-year stint with the Angels, Rodney was far from a hot commodity. The Rays took a chance and he rewarded them with one of the best seasons in MLB history by a reliever. He nailed down 48 of 50 save chances in 2012 with a minuscule 0.60 ERA, 0.78 WHIP and 9.2 K/9 in 76 appearances. He added 37 more saves in his second season, before walking in free agency.

          

    No. 2: SP Charlie Morton—Dec. 21, 2018

    Terms: Two years, $30 million (3.4x league avg)

    The $15 million that Morton earned last season accounted for 23.4 percent of the Rays' payroll, according to Spotrac. That's a significant piece of the pie for one player, and potentially disastrous for a small-market team if it doesn't work out. Luckily, it did, as he went 16-6 with a 3.05 ERA, 1.08 WHIP and a career-high 240 strikeouts in 194.2 innings to finish third in AL Cy Young voting.

         

    No. 3: 2B Akinori Iwamura—Dec. 15, 2006

    Terms: Three years, $7.7 million (0.9x league avg)

    Perhaps the most underrated Japanese import of all-time, Iwamura hit .281 with a .354 on-base percentage and 6.6 WAR in his three seasons with the Rays. He was the everyday second baseman on the 2008 team that reached the World Series, and he hit .273 in 73 plate appearances with six extra-base hits, five RBI and eight runs scored in 16 postseason games that year.

Texas Rangers

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    Adrian Beltre
    Adrian BeltreTony Gutierrez/Associated Press

    No. 1: 3B Adrian Beltre—Jan. 5, 2011

    Terms: Six years, $96 million (4.4x league avg)

    After rebuilding his value on a one-year deal with the Red Sox in 2010, Beltre was able to secure a six-year deal from the Rangers in what easily goes down as the best signing in franchise history. The future Hall of Famer hit .308/.358/.516 for a 132 OPS+ with 167 home runs, 563 RBI and 37.5 WAR in his first six seasons with the Rangers, finishing in the top 10 in AL MVP voting four times while winning three Gold Gloves.

          

    No. 2: SP Colby Lewis—Jan. 19, 2010

    Terms: Three years, $8 million (0.9x league avg)

    Back from a stellar two-year stint in Japan, Lewis returned to where he began his pro career as a first-round pick in the 1999 draft when he signed a two-year, $5 million deal that included a $3 million club option for 2012. He quickly became a key rotation piece for the Rangers teams that won back-to-back AL pennants in 2010 and 2011, starting 64 games and posting a 4.06 ERA (110 ERA+) during that two-year span. Aside from his regular-season success, he also had a 2.34 ERA in 50 innings of work during those two playoff runs.

          

    No. 3: 1B Rafael Palmeiro—Dec. 4, 1998

    Terms: Five years, $45 million (4.4x league avg)

    Despite being 34 years old at the onset of this deal, Palmeiro remained one of the game's most productive power hitters, averaging 43 home runs and 122 RBI with a 140 OPS+ over the course of the contract. He hit his 500th career home run during the final year of the contract, in what was the 10th 30-homer season of his career.

Toronto Blue Jays

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    Paul Molitor
    Paul MolitorRich Pilling/Getty Images

    No. 1: DH Paul Molitor—Dec. 7, 1992

    Terms: Three years, $13 million (3.9x league avg)

    The Blue Jays signed a 36-year-old Molitor to replace another future Hall of Famer in Dave Winfield after winning the World Series in 1992. He hit .332/.402/.509 with 211 hits, 37 doubles, 22 home runs, 111 RBI and 22 steals in 1993 to finish second in AL MVP voting, and that success carried over into October where he went 21-for-47 with 10 extra-base hits in 12 games and took home World Series MVP honors. He was worth 10.5 WAR in his three seasons with the team, despite serving almost exclusively as a DH.

          

    No. 2: SP Roger Clemens—Dec. 13, 1996

    Terms: Four years, $40 million (6.4x league avg)

    In his two seasons with the Blue Jays, Clemens went 41-13 with a 2.33 ERA, 1.06 WHIP and a staggering 20.1 WAR, winning back-to-back Cy Young Awards in the process. With that, he effectively rejoined the ranks of the game's elite after a disappointing final two seasons in Boston. He was traded to the Yankees prior to the third year of his contract in exchange for David Wells, Graeme Lloyd and infield prospect Homer Bush.

          

    No. 3: SP Jack Morris—Dec. 18, 1991

    Terms: Two years, $10.85 million (5.8x league avg)

    On the heels of his legendary 10-inning shutout in Game 7 of the 1991 World Series, Morris joined a Blue Jays team ready for an October run of its own. He went 21-6 with a 4.04 ERA in 240.2 innings as the ace of the Toronto staff in 1992, finishing fifth in AL Cy Young voting in the process. He struggled mightly in year two, posting a 6.19 ERA in 27 starts, but his role in helping launch Toronto's back-to-back World Series winners still earns him a spot.

Washington Nationals

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    Max Scherzer
    Max ScherzerEvan Vucci/Associated Press

    No. 1: SP Max Scherzer—Jan 21, 2015

    Terms: Seven years, $210 million (5.7x league avg)

    We're just five years into this monster contract, but what a five years it's been. So far, Scherzer has gone 79-39 with a 2.74 ERA (156 ERA+), 0.94 WHIP and 1,371 strikeouts in 1,050.2 innings, good for 34.9 WAR. He won NL Cy Young honors in 2016 and 2017, and finished in the top five in voting each of the other three seasons. It's not hyperbole to say that since joining the Nationals, he's cemented his place as a future Hall of Famer and one of the best pitchers of his era.

          

    No. 2: 2B Daniel Murphy—Jan. 6, 2016

    Terms: Three years, $37.5 million (2.8x league avg)

    A huge 2015 postseason made Murphy a hot commodity on the free-agent market, and the Nationals took the leap with a three-year deal. He immediately took his game to another level. In his first two seasons with the team, he hit .334/.387/.569 for a 145 OPS+ while averaging 45 doubles, 24 home runs and 98 RBI, winning a pair of Sliver Sluggers and finishing second in NL MVP voting in 2016. He was limited by injuries in the third year and eventually traded to the Cubs, but he made his mark in his brief time with the franchise.

          

    No. 3: SP Patrick Corbin—Dec. 7, 2018

    Terms: Six year, $140 million (3x league avg)

    It's probably too early to be including Corbin just one year into a six-year deal. However, the alternatives are uninspiring at best, and he was a key piece of the championship puzzle in 2019. The southpaw posted a 3.25 ERA and 1.18 WHIP with 238 strikeouts in 202 innings during the regular season, then made three starts and five relief appearance during the playoffs, including three scoreless innings of relief in Game 7 of the World Series.

         

    All stats courtesy of Baseball Reference and FanGraphs, while contract information came from a wide variety of sources, including Baseball Prospectus, Spotrac and old news articles. Average salary data via ESPN.com and Statista.com and can be found compiled in this doc.