1 of 45Otto Greule Jr/Getty Images; Johnny Nunez/WireImage
Five-time All-Star and Silver Slugger Robinson Cano is headed to Seattle after agreeing to a deal with the Mariners on Friday (Dec. 6). His agent, Jay-Z of the new Roc Nation Sports agency, got this offseason's biggest free agent prize a contract that will take Cano through his age-40 season. The second baseman with a career .309 average is just the fifth player to sign for over $200 million and the latest to join baseball's exclusive club of $100 million men.
2 of 45Chuck Solomon/SI
Only A-Rod, it seems, can beat A-Rod. After a monster 2007 season that resulted in his third AL MVP award, Rodriguez opted out of his record $252 million deal with three years remaining. He eventually wound up back with the Yankees, setting a new record for the richest contract in baseball history, one that includes potential bonuses for reaching certain milestones.
3 of 45Robert Beck/SI
The three-time NL MVP agreed to a $254 million, 10-year contract with the Los Angeles Angels. When Pujols signed a seven-year, $100 million deal with the Cardinals in 2004, it looked like the biggest bargain of them all. Pujols has established himself as the best pure hitter in the game, helped lead the Cardinals to World Series titles in 2006 and 2011. He won the 2005, '08 and '09 NL MVP awards and finished second in the voting for '06 and 2010.
4 of 45Brad Mangin/SI
Votto still has two years left on his current deal. He will make $9.5 million this season and $17 million in 2014 before the new contract kicks in. He's all set to be a Red through 2023, when he'll be 39 years old. The Reds drafted Votto in the second round in 2002 and guided him to stardom. The first baseman has delivered 119 home runs and 401 RBIs over the last four-plus seasons. He is a three-time All-Star and the 2010 National League MVP.
5 of 45John Biever/SI
It took until late January of 2012 but Prince Fielder finally found a new home, agreeing to a nine-year, $214 million deal with the Detroit Tigers. It is just the fourth contract worth more than $200 million. Fielder averaged 38 home runs in his six full seasons with the Brewers, made three All-Star teams and helped them reach the postseason twice.
6 of 45Chuck Solomon/SI
Thanks to A-Rod's 10-year, $252-million deal of 2001, the Yankees felt compelled to reward their own superstar shortstop, who, unlike Rodriguez, had actually won championships before. Jeter had four World Series rings when he signed this deal in 2001. In the final year of his contract, Jeter set career lows in batting average, on-base percentage and slugging percentage at 35. After the 2010 season, he agreed to a new three-year, $51 million contract that includes a player option for the 2014 season, a salary that made him the highest-paid shortstop in the game and still one of the 20 highest-paid players in baseball.
7 of 45John Iacono/SI
The once small-market Twins went to unprecedented (for them) financial lengths to keep hometown hero Joe Mauer in Minnesota, signing the St. Paul native to an eight-yer, $184 million deal in March 2010. Still just 26, Mauer had already won three batting titles an MVP and helped the Twins win two AL Central crowns.
8 of 45Damian Strohmeyer/SI
The 2011 AL MVP and Cy Young Award winner had been signed through 2014 and set to earn $20 million in each of the next two seasons. The new deal announced Friday, March 29, 2013, keeps those salaries and adds $140 million in new guaranteed money: $28 million each season from 2015-19. It includes a $22 million option for 2020 that would become guaranteed if he finishes among the top five in 2019 Cy Young voting. The deal could be worth $202 million over eight seasons. Verlander's agreement is the richest deal for a pitcher in baseball history.
9 of 45Chuck Solomon/SI
A switch-hitter with prodigious power, Mark Teixeira also has impeccable timing. His first foray into free agency coincided with the Yankees' vacancy at first base, and nobody spends like the Yankees. The Bronx Bombers agreed to terms with the former Angels slugger who, at the time, had hit 203 career home runs and didn't turn 29 until April 2009.
10 of 45Ted S. Warren/AP
King Felix agreed to a contract with the Mariners prior to the 2013 season that made him the highest-paid pitcher in baseball. There had been speculation and reports about an injury to three-time All-Star and 2010 AL Cy Young Award winner's pitching elbow that could have been slowing the negotiations. The three-time All-Star and 2010 AL Cy Young Award winner
11 of 45Chuck Solomon/SI
The San Francisco Giants and catcher Buster Posey agreed to an eight-year extension Friday, March 29, 2013, with a $21.4 million club option for 2022. Posey was under contract through the 2016 season, but this new deal buys out several years of free agency. The 2012 National League MVP hit .336 with 24 home runs and 103 RBI in 2012, leading the team to their second world championship in three seasons.
12 of 45Walter Iooss Jr./SI
CC Sabathia parlayed one of the great performances by a midseason acqusition into the richest contract ever given to a pitcher. Sabathia, who went 11-2 with a 1.65 ERA for the Milwuakee Brewers after a July trade from the Cleveland Indians, signed a seven-year $161 million deal with the Yankees, topping the previous mark for a pitcher by more than $20 million. He agreed to a new deal after the 2011 season, adding another year and $30 million with a team option for a seventh season.
13 of 45Robert Beck/SI
In his best season-to-date, the 27-year-old hit .324/.399/.586 and led the National League with 39 home runs and both leagues with 126 RBI in 2011. He also stole 40 bases, falling just one home run shy of joining the elite 40 stolen base and 40 home run club. The Dodgers agreed on an eight-year contract extension with Kemp.
14 of 45Chuck Solomon/SI
During the length of Ramirez's deal, the world saw the best and worst of Manny Being Manny: two World Series titles, a fearsome bat and puzzling lapses in hustle and attitude. Ramirez was traded to the Dodgers in July 2008 and signed a 2-year, $45 million contract with L.A. before the '09 season.
15 of 45Tim DeFrisco/SI
Troy Tulowitzki was already under contract for three more years at a very affordable $28.75 million when the Rockies inked him to a 10-year, $157.75 million deal after the 2010 season. Tulowitzki was just 26 at the time he signed his new deal and was coming off a season in which he made his first All-Star team and won his first Gold Glove award.
16 of 45Chuck Solomon/SI
Four months after acquiring Adrian Gonzalez from the San Diego Padres, the Red Sox signed the first baseman to the largest deal ever given by the club's current ownership. Manny Ramirez's eight-year, $160 million deal was signed by the club's previous owners. Gonzalez, 28, receives a $6 million signing bonus, $21 million per year from 2012-16 and $21.5 million per year in 2017 and 2018. From 2006-10 with the Padres, Gonzalez averaged 32 homers and 100 RBIs, with a .288 batting average and a .374 on-base percentage.
17 of 45Robert Beck/SI
The Tigers gave Cabrera a $153.3 million, eight-year deal in March 2008 after acquiring him in a December trade with the Florida Marlins. Cabrera posted career highs in HRs (an AL-best 37) and RBIs (126) in his first season in Detroit.
18 of 45Bill Kostroun/AP
The Yankees were shut out of the postseason for just the second time in the Wild Card Era, they watched their bitter rival waltz away with a championship, they were dragged through an ugly public feud with their star player and they watched their TV ratings and attendance numbers plummet. It was not a good year for the Empire. So how would the Empire respond to defeat, debacle, and humiliation? Like they always do: The Empire strikes back. The Yankees and Jacoby Ellsbury agreed to a seven-year, $153 million deal ( the third-richest ever contract for an outfielder) on Dec. 3, 2013.
19 of 45Damian Dovarganes/AP
The Los Angeles Dodgers and free-agent pitcher Zack Greinke agreed to a deal on Dec. 8, 2012. Greinke had his best season in 2009, when won the AL Cy Young Award pitching for the Kansas City Royals. That year, he was 16-8 with a 2.16 ERA. The right-hander has overcome well-chronicled bouts with anxiety and depression, which nearly led him to quit baseball before the 2006 season. Greinke had a 15-5 record with a 3.48 ERA and 200 strikeouts in 2012 with the Milwaukee Brewers and Los Angeles Angels.
20 of 45Al Tielemans/SI
When Cole Hamels and the Philadelphia Phillies agreed to a six-year, $144 million contract, he became the third Phillies' starter making at least $20 million per season. It's the largest contract signed by a Philadelphia athlete. The three-time All-Star and 2008 World Series MVP passed up an opportunity to possibly get more money on the open market to stay with the team that drafted him in 2002.
21 of 45Heinz Kluetmeier/SI
Just days after trading for star slugger Adrian Gonzalez, the Red Sox landed four-time All-Star outfielder Carl Crawford, weakening the division-rival Tampa Bay Rays and bolstering their own title chances in the process. Crawford is a true five-tool player, having won a Gold Glove, batted .300 five times, stole 45 or more bases seven times and hit double-digit home runs six times.
22 of 45Robert Beck/SI
With player salaries skyrocketing in 2001, the Rockies thought they should lock up the star first baseman for an entire decade. Helton had been in decline in recent years before helping to lead the Rockies to the 2007 NL pennant.
23 of 45Seth Wenig/AP
New York Mets third baseman David Wright agreed to the richest contract in franchise history on Nov. 30, 2012. The deal replaced Wright's $16 million salary for 2013 and includes $122 million in new money. A homegrown fan favorite and the face of the franchise, Wright is the club's career leader in several major offensive categories including hits, RBIs, runs and walks.
24 of 45Heinz Kluetmeier/SI
After months of pursuit the Mets finally agreed to a trade to acquire Santana, but the deal wasn't official until the Mets inked him to a contract extension. Not surprisingly, the two-time Cy Young winner became the highest-paid pitcher in baseball history (at the time), then went 16-7 with a 2.53 ERA in his debut season in Queens.
25 of 45Al Tielemans/SI
Questions about Soriano's power were answered after he hit 46 home runs while playing for the Nationals, whose home stadium was cavernous. With that kind of power, it's no wonder that Soriano's lack of a position doesn't seem to bother the Cubs, who signed him after 2006 and won the NL Central in his first two years with the club.
26 of 45Brad Mangin/SI
Cain's deal is the largest for a right-handed pitcher in baseball history. The agreement adds $112.5 million over five years to the $15 million salary for 2012 that was remaining in his previous deal. Cain gets a $5 million signing bonus as part of the new contract and $20 million annually from 2013-17. The deal includes a $21 million option for 2018 with a $7.5 million buyout that, if exercised, would raise the total to $141 million over seven seasons. In 2011, Cain was 12-8 with a 2.88 ERA and tossing 179 strikeouts.
27 of 45Brad Mangin/SI
The last remaining member of Oakland's Big Three finally left for the crosstown Giants before the 2007 season by accepting the largest deal ever at the time for a pitcher, eclipsing the old mark held by Mike Hampton (eight years, $121 million with the Rockies). In his first four seasons with San Francisco, Zito has gone just 40-57 with a 4.46 ERA.
28 of 45John Iacono/SI
The Blue Jays ensured their All-Star center fielder wouldn't leave via free agency after 2007 by signing him to this extension. Wells averaged 21 home runs and 90 RBIs from 2004-06 but he batted a career-low .245 in '07 and had only 15 home runs and 66 RBIs in '09. However, Wells did bounce back in 2010 with 31 homers and 88 RBIs.
29 of 45Ed Wolfstein/Icon SMI
The Nationals raised more than a few eyebrows when they opened the vault for this 31-year-old right fielder after the 2010 season. Over his first eight major league seasons, Werth batted .272 with 120 home runs but had yet to drive in 100 runs in a season and had appeared in just one All-Star Game.
30 of 45Simon Bruty/SI
The Nationals extended the third baseman's contract through 2019, adding six years and $100 million, according to The Associated Press. He already was signed for 2012 and 2013 for $26 million. Zimmerman, 27, was the Nationals' first draft pick after moving to Washington and owns a career .289 average with 128 home runs.
31 of 45John Cordes/Icon SMI
Texas had hoped to sign the 2010 AL Most Valuable Player, who led the Rangers to consecutive World Series appearances in 2010 and 2011, but Hamilton agreed to a contract with the Los Angeles Angels following the 2012 season. The 31-year-old was considered a risk by some teams because of his history of alcohol and substance abuse, which derailed his career before his surge with the Rangers over the past five seasons.
32 of 45Tim DeFrisco/SI
Howard joined the $100 million club by signing a five-year extension with the Phillies on April 26, 2010, worth a guaranteed $125 million. The deal also includes a club option for a sixth that could increase the deal's value to $138 million. Howard, 30, is one of only three players in history to win a Rookie of the Year award and follow it up with an MVP the next season. He averaged 49 home runs and 143 RBIs from 2006-09 and helped the Phillies win the 2008 World Series and the 2009 NL pennant, the same year he was named NLCS MVP.
33 of 45Chuck Solomon/SI
The star left-hander led the Mets to the 2000 NL pennant before hitting free agency. The pitching-starved Rockies scooped him up with this mega-contract that ended up being paid off by three teams -- Colorado, Florida and Atlanta and resulted in only 56 wins to date.
34 of 45Bob Rosato/SI
The Yankees and Rangers offered more money, but almost a year after they traded him to the Mariners, Lee opted to return to the Phillies, the team he helped pitch into the 2009 World Series. Lee joined Roy Halladay, Roy Oswalt and Cole Hamels to give Philadelphia what most observers felt was the best starting rotation in either league.
35 of 45John Iacono/SI
Giambi won the AL MVP with the Oakland A's in 2001, then bolted for the Bronx. The Yankees won only one pennant and no World Series with Giambi, who was one of a number of athletes who testified in the BALCO probe.
36 of 45David E. Klutho/SI
Matt Holliday joined baseball's $100 million club on Jan. 5, 2010, when he re-signed with the Cardinals. St. Louis rewarded Holliday with a contract that will pay him more than $17 million on average for each of the seven seasons and a full no-trade clause. Holliday batted .353 with 13 home runs and 55 RBIs in 63 games with the Cardinals after being acquired in a July '09 trade from the Oakland Athletics. He helped stabilize their batting order by providing a consistent power threat in the cleanup spot behind NL MVP Albert Pujols. When they added Holliday on July 24, the Cardinals led the NL Central by just 1 1/2 games, but by the end of August their lead had swelled to 10 games and they cruised to the division title.
37 of 45John Biever/SI
The 24-year-old Andrus is now owed $131 million over the next 10 seasons, including the money left on his current deal. Andrus is considered one of the top young shortstops in baseball. He was an All-Star in 2012, when he hit .286 with 31 doubles. But the investment is heavy for a player with a career .275 batting average and only 14 home runs in four seasons. The Rangers are betting that Andrus will continue to grow offensively.
38 of 45Chuck Solomon/SI
Mets fans are loathe to admit this, but Beltran reportedly would have played for the Yankees for a lot less money. Instead, he cashed in on his breakout 2004 postseason with the Astros by signing with the Mets, whom he led to within one game of the World Series in 2006.
39 of 45Bob Rosato/SI
Ken Griffey, Jr.
The Reds won 96 games in 1999, the year before trading for The Kid and signing him to this massive contract extension. They hadn't won more than 85 games in a season since and finally traded the injury-plagued Griffey to the White Sox in July 2008.
40 of 45Chuck Solomon, Winslow Townson/SI
Dustin Pedroia and the Boston Red Sox have reportedly agreed on an eight-year contract extension worth $110 million ? the most ever for a second baseman ? and will stretch through 2021, with Pedroia owning a full no-trade clause. Pedroia has been a franchise cornerstone in Boston since his rookie year in 2007, when the Red Sox won the World Series and he won AL Rookie of the Year after hitting .317. The next season, Pedroia hit a career-high .326 with 54 doubles and scored 118 runs to win Most Valuable Player.
41 of 45Jeffery A. Salter/SI
The Miami Marlins kicked off the 2011 offseason by landing prized shortstop Jose Reyes with a six-year, $106 million contract. The deal gave the Marlins the big name they wanted to open their new stadium along with an electric two-way player that is a four-time All-Star and reigning NL batting champ.
42 of 45John Biever/SI
The Brewers signed Braun to a five-year contract extension in April 2011 that guarantees the All-Star an additional $105 million on top of his current deal and will run at least through the 2020 season. Braun gets a $10 million signing bonus and will make salaries of $19 million in 2016-18, $18 million in 2019, $16 million in 2020. The mutual option for 2021 is worth up to $20 million with a $4 million buyout. Braun signed a $45 million, seven-year extension in 2008 after winning the NL Rookie of the Year in 2007, which was the largest contract ever by a player with less than one year of service time.
43 of 45Bob Rosato/SI
The Dodgers lured Brown away from the Padres in free agency after the 1998 season with the biggest contract in history at the time. Brown pitched well, though not spectacularly, for the Dodgers in parts of five non-playoff seasons before being traded to the Yankees.
44 of 45Damian Strohmeyer/SI
Tampa Bay Rays third baseman Evan Longoria agreed to a new contract through 2022 that adds six guaranteed seasons and $100 million. The agreement announced Monday Nov. 26, 2012, with the three-time All-Star incorporates the remainder of the 27-year-old's existing contract, which called for him to earn $36.6 million over the next four seasons. The new deal includes a team option for 2023.
45 of 45John Biever/SI
The Astros finally addressed their woeful offense by signing this All-Star slugger away from the Texas Rangers after the 2006 season. From 2007-09, Lee hit at least .300 with 100 RBIs each season. In 2010, Lee batted a career-low .246 with a .291 OBP, yet still managed to hit 24 home runs with 89 RBIs.
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