LHP Randy Johnson (four years, $52.4 million in Dec. 1998)
Teams are listed alphabetically, though it's fitting we start with one of the best free-agent signings in history and easiest calls on our list. The D-Backs gave Johnson a four-year deal and he rewarded them with four Cy Youngs, a World Series title (he was World Series co-MVP), and a 2.48 ERA with 1,417 strikeouts in 1,030 innings. Johnson hung around Arizona beyond his original four-year deal, though the four years covered by this contract were the apex of an inner-circle Hall of Fame career.
Honorable mention: 2B Jay Bell, OF Steve Finley, RHP Zack Greinke
RHP Greg Maddux (five years, $28 million in Dec. 1992)
The Braves landed Maddux, then only 26 and coming off his first Cy Young, with the richest pitching contract in history at the time. Over the next five years he finished first, first, first, fifth, and second in the Cy Young voting, and threw 1,156 1/3 innings with a 2.13 ERA. It is simply one of the greatest five-year stretches in baseball history. Maddux was also instrumental to the club's 1995 World Series win, their first title since the franchise moved to Atlanta in 1966. One of the greatest free-agent signings in sports history, hands down.
Honorable mention: OF Brian Jordan, 3B Terry Pendleton, OF Lonnie Smith
1B Rafael Palmeiro (five years, $30.5 million in Dec. 1993)
Palmeiro's career and tenure with the Orioles ended in shame, though that was his second stint with the team from 2004-05. From 1994-98, he was one of the game's top run producers, authoring a .292/.371/.545 batting line that was 34 percent better than the league average hitter once adjusted for ballpark. Palmeiro averaged 36 homers those five seasons and remember, 1994 and 1995 were shortened by the strike. He led the O's to the ALCS in 1996 and 1997.
Honorable mention: 2B Roberto Alomar
DH David Ortiz (one year, $1.25 million in Jan. 2003)
For reasons that will never make sense, the Twins non-tendered Ortiz following a 20-homer season in 2002, paving the way for the Red Sox to sign a player who would become a franchise legend. Big Papi slugged 31 homers with a .288/.369/.592 batting line in 2003, the first year of 14-year run in Boston. Ortiz helped the Red Sox end their 86-year World Series drought in 2004, and led them to two more titles in 2007 and 2013 as well.
Honorable mention: OF Johnny Damon, OF/DH JD Martinez, OF Manny Ramirez
LHP Jon Lester (six years, $155 million in Dec. 2014)
The Cubs were ready to make the jump from Lovable Loser to World Series contender in 2015 and Lester gave them a bona fide ace, and also brought legitimacy to their title hopes. He finished second in the Cy Young voting in 2016 and was a central figure in their first championship in 108 years. The last two years of the contract weren't pretty, but Lester pitched to a 3.33 ERA and averaged over 190 innings during the first four years of the deal. He was a true frontline starter who made a lasting impact on the franchise.
Honorable mention: OF Moises Alou, OF Andre Dawson, UTIL Ben Zobrist
C Carlton Fisk (five years, $2.9 million in March 1981)
The Red Sox missed the deadline to tender Fisk a contract in Dec. 1980 and an arbitration panel declared him a free agent weeks later. Fisk didn't sign until after spring training opened, but he never missed a beat, going to the All-Star Game in 1981 and finishing third in the MVP voting in 1982. The Hall of Famer signed with the White Sox at 33 and some thought he was nearing the end of the line, but Fisk authored a .250/.315/.444 line with strong defense behind the plate during the five-year contract, and he hung around for another seven seasons on the South Side after that.
Honorable mention: 1B José Abreu, OF Jermaine Dye
OF Dave Parker (two years, $2.07 million in Dec. 1983)
Similar to Fisk, there was some thought the then 33-year-old Parker was on the decline when the Reds signed him away from the rival Pirates. Instead, he proved to have plenty left in the tank, and went on to post a pair of top-five finishes in the MVP voting in what became a four-year stint with Cincinnati. Parker hit .299/.347/.482 with 50 home runs during his initial two-year contract, and was runner-up to Willie McGee for the 1985 MVP award.
Honorable mention: RHP Francisco Cordero, OF Ron Gant
2B Roberto Alomar (four years, $30 million in Dec. 1998)
A down 1997 season at age 30 scared a few teams into thinking Alomar's best days were behind him (the second base aging curve is pretty brutal), but Cleveland was undeterred, and during the first three years of his contract Alomar hit .323/.405/.515 with Gold Glove-caliber defense. He earned a pair of top-four finishes in the MVP voting. Alomar's decline arrived in Year 4 of the deal, though Cleveland traded him to the Mets for three young players before the season, so it wasn't a problem. Getting three elite seasons out of a four-year deal is a major win for the team.
Honorable mention: DH Ellis Burks, RHP Orel Hershiser, OF Kenny Lofton, RHP Dennis Martinez
OF Larry Walker (four years, $22 million in April 1995)
The Expos slashed payroll following the 1994-95 strike, so much so that the team didn't offer Walker arbitration, allowing him to become a free agent and sign elsewhere without Montreal getting a draft pick in return. He hooked on with the two-year-old Rockies and hit .335/.414/.643 and averaged 32 homers per year during that four-year contract, even while missing time with injuries. Walked was named MVP in 1995 after hitting an outrageous .366/.452/.720 with 46 doubles and 49 home runs. He signed with Colorado in April 1995 and hung around until being traded at the 2004 deadline.
Honorable mention: OF Ellis Burks, OF Michael Cuddyer, 1B Andrés Galarraga
C Ivan Rodriguez (four years, $40 million in Feb. 2004)
Very close call here. Tony Phillips (three years, $4 million in Dec. 1989) put up a .375 on-base percentage while playing six different positions during his contract, making him an extremely valuable player. Rodriguez represented a changing of the guard, however. The Tigers went 43-119 in 2003 and were a laughing stock, but Rodriguez was a star in his prime, and the franchise's first step back toward respectability. Rodriguez hit .298/.326/.453 with top-notch defense during the four-year contract. He went to four All-Star Games, won three Gold Gloves, received MVP votes in 2004, and was the No. 3 hitter on their 2006 AL pennant team.
Honorable mention: 3B Darrell Evans, 1B Cecil Fielder, UTIL Tony Phillips
RHP Nolan Ryan (four years, $4.5 million in Nov. 1979)
With this contract Ryan became the first player to earn more than $1 million in a season. He was two months shy of his 33rd birthday at the time, and that four-year contract produced a 2.91 ERA with 768 strikeouts in 829 1/3 innings (and one of his record seven no-hitters). Ryan led the Astros to their first ever postseason berth in 1980 and twice received Cy Young votes during this contract. He spent a total of nine seasons with the Astros. It was a landmark signing for an organization that, up to that point, had a winning record only three times in its first 18 seasons.
Honorable mention: RHP Roger Clemens, 2B Jeff Kent, RHP Charlie Morton, LHP Andy Pettitte
RHP David Cone (three years, $18 million in Dec. 1992)
This was a homecoming for Cone in more ways than one. He grew up in Kansas City, was originally drafted by the Royals in 1981, and made his MLB debut for them in 1986 before being traded away. This contract made Cone the highest-paid pitcher in baseball for a few hours (the Braves sign Maddux soon thereafter) and included an upfront $9 million signing bonus, which was unprecedented at the time. Cone won the Cy Young in 1994 and had a 3.17 ERA in 415 2/3 innings in the first two years of the contract. The Royals traded him to the Blue Jays prior to the third year.
Honorable mention: OF Melky Cabrera, DH Kendrys Morales, RHP Edinson Vólquez
OF Vladimir Guerrero (five years, $70 million in Jan. 2004)
Only 28 at the time of the signing, Vlad Sr. was a five-tool superstar who was named MVP in the first year of the contract and later became the first player with an Angels hat on his Hall of Fame plaque. Guerrero hit .323/.387/.557 with 158 home runs during the five-year contract, and received MVP votes all five seasons (including two third-place finishes). He spent a sixth year with the Angels before moving on later in his career. All big-money free-agent contracts should work out this well.
Honorable mention: OF/DH Don Baylor, 2B Bobby Grich, OF Torii Hunter
IF Justin Turner (minor-league contract in Feb. 2014)
This is a tough one. Kirk Gibson signed a three-year, $4.5 million contract in Jan. 1988 and was named MVP that year, and also hit one of the most iconic home runs in baseball history in the World Series. Injuries sabotaged his career after that though (Gibson played only 160 games in the final two years of his three-year deal), allowing Turner to get the spot on our list. He originally signed a minor-league deal with Los Angeles believed to be worth $1 million at the MLB level, but he made the Opening Day roster that year, and has been a lineup mainstay since. That minor-league deal spawned an eight-year (and counting) career with the Dodgers that includes a .298/.379/.498 batting line and one World Series title.
Honorable mention: OF Kirk Gibson, RHP Zack Greinke
RHP Kevin Brown (three years, $12.6 million in Dec. 1995)
Brown was a good pitcher who became a great pitcher immediately upon joining the Marlins. He threw 233 innings with a 1.89 ERA in 1996 and finished second to John Smoltz in the Cy Young voting. The next year Brown threw 237 1/3 innings with a 2.69 ERA, and was the ace of the franchise's first World Series winner. The Marlins traded Brown to the Padres in their post-1997 fire sale, though those two years were plenty good enough to land him on this list.
Honorable mention: OF Moises Alou, 1B Carlos Delgado, LHP Al Leiter
OF Lorenzo Cain (five years, $80 million in Jan. 2018)
The pickings are slim for the Brewers. They have not had much success (or been all that active) in free agency, which made the Cain signing so shocking. It was very out of character. Cain hit .308/.395/.417 with top-of-the-line defense in Year 1 of his five-year contract, which earned him a seventh-place finish in the MVP voting and helped the Brewers win their first division title in six years (and only their second in 35 years). There's still one more year to go on Cain's deal and Years 2-4 weren't nearly as productive as Year 1, but Year 1 was good enough to get him on this list.
Honorable mention: 3B Sal Bando, OF Mike Cameron, 2B Willie Randolph
DH Chili Davis (two years, $4.5 million in Jan. 1991)
The Twins won the World Series in 1987 and then spun their wheels a bit from 1988-90, so, during the 1990-91 offseason, they brought in Davis to fortify the lineup and Jack Morris to strengthen the rotation. Davis was arguably the team's best hitter during their 1991 World Series run and he hit .282/.385/.476 with 41 home runs in his two years with Minnesota. Morris was very good as well, and he had that memorable 10-inning performance in Game 7 of the World Series. Davis gets the nod here because he gave the Twins two excellent seasons. Morris only played the one year with Minnesota.
Honorable mention: DH Nelson Cruz, RHP Jack Morris, DH Jim Thome
OF Carlos Beltrán (seven years, $119 million in Jan. 2005)
Beltrán practically begged the Yankees to sign him in Jan. 2005, but he wound up across town with the Mets, where he was highly productive and also unfairly criticized throughout his tenure. He hit a then-franchise record 41 home runs in 2006 and put up a strong .280/.369/.500 batting line with excellent defense for the Amazin's. Beltrán was traded to the Giants for Zack Wheeler in the seventh year of the seven-year deal, which was a nice going away present. Beltrán went to five All-Star Games in the seven years and received MVP votes in four seasons, including a fourth-place finish in 2006.
Honorable mention: RHP R.A. Dickey, 1B John Olerud, 3B Robin Ventura
OF Reggie Jackson (five years, $2.9 million in Nov. 1976)
The Yankees have signed a lot -- a lot -- of marquee free agents over the years, so we have no shortage of candidates to consider, but Jackson is still the straw that stirs the drink. The then-30-year-old Jackson joined a Yankees team that lost the World Series the previous year and had gone 14 years without a title, then the longest drought in franchise history. He hit .281/.371/.526 with 144 home runs during the five-year contract, led the Yankees to the 1977 and 1978 World Series titles, and was World Series MVP in 1977 thanks to his three-homer performance in the Game 6 clincher. Jackson was an All-Star and received MVP votes all five years in the Bronx.
Honorable mention: 1B Jason Giambi, OF Hideki Matsui, RHP Mike Mussina, LHP CC Sabathia
RHP Dave Stewart (one-year, pro-rated minimum in May 1986)
Prior to joining his hometown Athletics, Stewart was a journeyman who played for three teams in the three previous seasons. The Phillies released him in May 1986, he signed with the A's soon thereafter (the Orioles gave him a tryout too), and they helped him add a forkball that turned him into one of the game's most dominant pitchers. Stewart won 20 games four straight years from 1987-90, finished top four in the Cy Young voting four straight years, and was World Series MVP in 1989. He went from midseason scrap heap pickup to the ace of a team that won three straight pennants.
Honorable mention: OF Yoenis Céspedes, OF Dave Henderson, RHP Mike Moore
1B Pete Rose (four years, $3.225 million in Dec. 1978)
The Phillies became the Phillies in 1890, and from 1890-1975, the team went to the postseason just twice (1915 and 1950 World Series losses). Then, from 1976-79, they made the NLCS each year, but again lost. In an effort to get over the hump, Philadelphia signed Rose, then 37, to a four-year deal that made him the highest-paid player in baseball. Rose was an All-Star all four years of that contract, hitting .300/.375/.376 overall. Most importantly, he led the franchise to its first ever World Series title in 1980. Rose spent another year with the Phillies beyond this initial four-year contract before moving on.
Honorable mention: OF Bryce Harper, LHP Cliff Lee, 1B Jim Thome
C Russell Martin (two years, $17 million in Nov. 2012)
To say the Pirates have been historically inactive in free agency would be an understatement. There are just no significant long-term deals to consider here. Pittsburgh ended its 20-year postseason drought in 2013 thanks to large part to Martin, who was excellent behind the plate and productive at it, hitting .256/.362/.401 with 26 home runs during his two years with the team. Martin's all-around game at a premium position helped the Pirates to their most successful run in two decades.
Honorable mention: LHP Francisco Liriano, OF Reggie Sanders
RHP Chris Carpenter (one year, $300,000 in Dec. 2002)
A former first-round pick, Carpenter battled injuries and ineffectiveness early in his career with the Blue Jays, and he missed the entire 2003 season with elbow and shoulder surgery. When he returned in 2004, he was an instant ace, and he finished his career having thrown over 1,300 innings with a 3.07 ERA with St. Louis. Carpenter was the Comeback Player of the Year in 2004 and the Cy Young winner in 2005 (he had two other top-three Cy Young finishes too), and he was the No. 1 starter during the team's 2006 and 2011 title runs. The original one-year contract was lost to injury, but getting Carpenter in the organization and what came next gets him this spot.
Honorable mention: RHP Jason Isringhausen, C Darrell Porter
1B Steve Garvey (five years, $6.6 million in Dec. 1982)
Signing Garvey, an eight-time All-Star and four-time pennant-winner (and one-time World Series champ), away from the rival Dodgers was a watershed moment for the Padres. They had been a pushover since joining the league as an expansion team in 1969, and the Garvey signing signaled their intent to become a legitimate contender. Sure enough, Garvey went to two All-Star Games with San Diego and led the team to the 1984 NL pennant. His two-run walk-off homer against Cubs closer Lee Smith in Game 4 of the 1984 NLCS very well might be the biggest hit in franchise history.
Honorable mention: RHP Goose Gossage, 3B Manny Machado, C Gene Tenace
OF Barry Bonds (six years, $43 million in Dec. 1992)
At the time of this signing Bonds was already a two-time MVP and he was still only 28 years old. I reckon he would have fetched close to $400 million in today's market. As it stands, this contract made him the highest-paid player in baseball. Bonds won his third MVP in his first year with the Giants, when he slugged 46 home runs and hit .336/.458/.677. During this six-year contract Bonds authored a .307/.445/.617 batting line and averaged 39 home runs and 32 stolen bases per season. He was an All-Star all six years, won five Gold Gloves, and four times he finished in the top five of the MVP voting. Bonds' record-breaking stay in San Francisco lasted 14 years.
Honorable mention: OF Brett Butler, OF Willie McGee
OF Ichiro Suzuki (three years, $14.088 million in Nov. 2000)
Although he was technically an MLB rookie, Ichiro was a 27-year-old Japanese league veteran who stepped right into the Mariners lineup in 2001. He joined Fred Lynn as the only players to be named Rookie of the Year and MVP in the same season that year, and would go on to hit .328/.374/.440 with 121 stolen bases and all-world defense during the initial three-year contract. Suzuki of course played 14 seasons with Seattle overall, and is one of the most important players of the last 25 years or so. The Mariners paid his former team in Japan, the Orix Blue Wave, a $13.125 million posting fee to acquire his negotiating rights, so it was a touch over $27 million all-in to get Ichiro from 2001-03. It was well, well worth it.
Honorable mention: 2B Bret Boone, DH Nelson Cruz, 1B John Olerud
RHP Charlie Morton (two years, $30 million in Dec. 2018)
The Rays run shoestring payrolls, so when they spend money in free agency, they really have to nail it, and they certainly did with Morton. The 35-year-old finished third in the Cy Young voting his first season with Tampa, throwing a career high 194 2/3 innings with 240 strikeouts and a 3.05 ERA. He helped Tampa snap their five-year postseason drought and won the Wild Card Game that year as well. Year 2 of Morton's contract was cut short by the COVID-19 pandemic, and the Rays surely wish they'd kept him around in 2021 rather than decline his $15 million club option.
Honorable mention: 3B Wade Boggs, 2B Akinori Iwara, RHP Fernando Rodney
3B Adrián Beltré (six years, $96 million in Jan. 2011)
Beltré signed with the Rangers at age 32, yet he was already 13 years into his big league career. He aged exceptionally well -- well enough that he'll wear a Rangers cap into the Hall of Fame -- hitting .305/.358/.516 with an average of 28 homers per season to go along with best-at-the-position caliber defense during the six-year contract. Beltré received MVP votes in all six seasons and finished as high as third in the voting, with three seventh-place finishes. Texas signed him after going to the franchise's first World Series in 2010 and he got them back in the Fall Classic the next year.
Honorable mention: 1B Rafael Palmeiro, RHP Colby Lewis, SS Alex Rodriguez, RHP Nolan Ryan
DH Paul Molitor (three years, $13 million in Dec. 1992)
Close call here, but I'll take one World Series title over two Cy Youngs, so Molitor gets the nod over Roger Clemens (four years, $40 million in Dec. 1996). The Blue Jays won the World Series in 1992, then brought in Molitor to replace fellow Hall of Famer Dave Winfield at DH, and he hit .332/.402/.509 with a career high 22 home runs as Toronto repeated as World Series champs. Molitor was the MVP runner-up to Frank Thomas and won World Series MVP honors that year. During his three years with the Blue Jays, Molitor put up a .315/.387/.484 batting line at ages 36-38.
Honorable mention: RHP Roger Clemens, RHP Jack Morris, OF Dave Winfield
RHP Max Scherzer (seven years, $210 million in Jan. 2015)
We started with an easy call and we're going to finish with an easy call. At the time, Scherzer's contract was the record for a pitcher who changed teams, and it has gone down as one of the best free-agent contracts in history. Scherzer had a 2.80 ERA with 1,610 strikeouts in 1,229 innings with Washington, and of course led them to the franchise's first World Series title in 2019. He won two Cy Youngs during the contract, was runner-up once, and finished third in the voting twice. Scherzer is all but certain to be the first player to wear a Nationals hat into the Hall of Fame.
Honorable mention: 2B Daniel Murphy, OF Jayson Werth
