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MLB 49 43 Baseball's longest contracts 30447314 Todd Helton: Rockies, 11 years, $151.5 million Todd+Helton%3A+Rockies%2C+11+years%2C+%24151.5+million MLB

Benefitting from the hitter-friendly conditions at home, Helton was among the most productive hitters in baseball when Colorado gave him a nine-year extension in 2001 with two years remaining on his existing contract. He remained highly productive for seven seasons before the Coors Field humidor and back problems brought him back toward the league average. The Rockies nearly dumped his salary on the Red Sox in 2007. When that deal fell through, they were unable to move him for the duration of the deal.

Charles Rex Arbogast - AP Images
MLB 49 43 Baseball's longest contracts 30447319 Alex Rodriguez: Rangers, 10 years, $252 million and Yankees, 10 years, $275 million Alex+Rodriguez%3A+Rangers%2C+10+years%2C+%24252+million+and+Yankees%2C+10+years%2C+%24275+million MLB

A-Rod is the only player to cash two megadeals, each one a major league record for total value. He jumped from the Mariners to the Rangers in 2001 and delivered 156 home runs in three seasons in Texas. But the Rangers never had a winning season with Rodriguez and soon found his contract prevented them from building around him. He went to the Yankees after the 2003 season. His production remained high, and an opt-out clause in the original deal enabled him to get the Yankees to commit to even more money and years in 2008. A-Rod became a favorite of the gossip pages and was forced to come clean about steroid use that helped him to those monster stats. He has been a lightning rod in New York but did earn his only World Series ring with the Yankees in 2009.

Anthony Gruppuso - USA TODAY Sports
MLB 49 43 Baseball's longest contracts 31665315 Albert Pujols: Angels, 10 years, $240 million Albert+Pujols%3A+Angels%2C+10+years%2C+%24240+million MLB

The Los Angeles Angels shocked the baseball world at the winter meetings in 2011, reaching an agreement with free-agent first baseman Albert Pujols on a guaranteed $240 million, 10-year contract. The slugger's deal includes a personal-services agreement worth at least another $10 million. Pujols, 31, received a full no-trade clause. His contract, befitting the game's premier player, will be the second-highest in major league history, behind Alex Rodriguez’s 10-year, $275 million deal.

Scott Rovak - USA TODAY Sports
MLB 49 43 Baseball's longest contracts 30862928 Joey Votto: Reds, 10 years, $225 million Joey+Votto%3A+Reds%2C+10+years%2C+%24225+million MLB

On April 2, 2012, Votto, the 2010 NL MVP, signed a 10-year, $225 million deal that takes him through 2023. It was the fourth largest deal in MLB history. His average annual salary is $22.5 million. The Reds, however, don't have a great history with long-term deals. Remember Ken Griffey Jr.'s deal?

Jeff Curry - USA TODAY Sports
MLB 49 43 Baseball's longest contracts 30444432 Derek Jeter: Yankees, 10 years, $189 million Derek+Jeter%3A+Yankees%2C+10+years%2C+%24189+million MLB

The Yankees rewarded their captain in 2001, an acknowledgement that, at age 26, he already ranked among the great figures in franchise history. Jeter maintained a remarkable consistency throughout the course of the contract and moved past Ruth, Gehrig and Mantle on many of the Yankees’ career offensive charts. He was the face of the franchise at the start of the deal, and that was even more true at the end. Remarkable.

Joy R. Absalon-US PRESSWIRE -
MLB 49 43 Baseball's longest contracts 31661671 Troy Tulowitzki: Rockies, 10 years, $157.75 million Troy+Tulowitzki%3A+Rockies%2C+10+years%2C+%24157.75+million MLB

Having been burned by megadeals with Mike Hampton and Todd Helton before, the Rockies nonetheless forged ahead with their star shortstop after the 2010 season. With three years left on his contract, Colorado extended the deal another seven years. Despite a broken wrist at midseason, Tulowitzki delivered in 2011: .302 batting average, 30 home runs, 105 RBI.

Steve Mitchell-US PRESSWIRE - USA TODAY Sports
MLB 49 43 Baseball's longest contracts 30442523 Ryan Braun: Brewers, 10 years, $145.5 million Ryan+Braun%3A+Brewers%2C+10+years%2C+%24145.5+million MLB

In April of 2011, the Brewers and their star left fielder agreed on a five-year extension even though he was in the middle of a seven-year contract. The reworked deal carries through 2020. Braun traded long-term security for a potential free-agent bonanza. The Brewers, meanwhile, devoted so much of their resources to Braun that they opted to let Prince Fielder go. All Braun did after the new deal was finalized was win the National League MVP award. After successfully appealing a 50-game suspension following a positive drug test during the 2011 offseason, the future is bright for Braun.

Jeff Curry - USA TODAY Sports
MLB 49 43 Baseball's longest contracts 30442521 Dave Winfield: Yankees, 10 years, $23 million Dave+Winfield%3A+Yankees%2C+10+years%2C+%2423+million MLB

Winfield was the game’s highest-paid player after bolting San Diego following the 1980 season. Despite his 1-for-22 performance in the 1981 World Series, he was an All-Star performer in New York. He ran afoul of Yankees owner George Steinbrenner, however, because his contract contained a cost-of-living clause that escalated its value. Steinbrenner thought he had been hoodwinked and hired a gambler to dig up dirt on Winfield. That got Steinbrenner suspended from the sport for the second time. Winfield was traded to the Angels in the final year of the deal.

Guy Boudia - AP Images
MLB 49 43 Baseball's longest contracts 30442527 Wayne Garland: Indians, 10 years, $2.3 million Wayne+Garland%3A+Indians%2C+10+years%2C+%242.3+million MLB

Full free agency was in its first winter when Garland left Baltimore after a 20-win season in 1976. Teams were still figuring out which economic strategies worked best. The Indians tried a long-term path with Garland at a relatively low annual cost. It might have worked with a better pitcher. Garland was a one-season wonder who led the American League in losses in his first year in Cleveland and never exceeded six wins after that. He was released halfway through the deal.

Tony Tomsic - Getty Images
MLB 49 43 Baseball's longest contracts 30442424 Ken Griffey Jr.: Reds, 9 years, $116.5 million Ken+Griffey+Jr.%3A+Reds%2C+9+years%2C+%24116.5+million MLB

After pulling off the blockbuster trade with Seattle in spring 2000, the Reds quickly wrapped up the Cincinnati hometown hero. He did everything expected in his first year, hitting 40 home runs with 118 RBI. He was an All-Star only twice more during the duration of the deal, however, as a series of injuries sapped him of his bat speed and athleticism in center field. The Reds tried repeatedly to move his salary off the books, succeeding only toward the end of the final year.

Kyle Terada - USA TODAY Sports
MLB 49 43 Baseball's longest contracts 30442425 Joe Mauer: Twins, 8 years, $184 million Joe+Mauer%3A+Twins%2C+8+years%2C+%24184+million MLB

Moving into Target Field in 2011, the Twins did not want to let a hometown star like Mauer put a damper on the new era by walking as a free agent. Before the first season in the new stadium, they inked him to the whopper of an extension that brings Mauer $23 million every season. Year 1 of the pact was a disaster. Offseason knee surgery didn’t heal well, and Mauer played only 82 games while the organization and outsiders debated whether he could continue to play catcher.

Tony Gutierrez - AP Images
MLB 49 43 Baseball's longest contracts 30444416 Mark Teixeira: Yankees, 8 years, $180 million Mark+Teixeira%3A+Yankees%2C+8+years%2C+%24180+million MLB

The Yankees won a bidding war with the Red Sox for the services of the first baseman following the 2008 season. They received Gold Glove defense and elite power. He has shown consistent power, hitting at least 33 home runs and 100 RBI in his first three seasons in New York — he dipped to 24 homers and 84 RBI in 2012, limited to 123 games because of an injury. His overall production, however, has yet to match his level from the two years before free agency. Is he on cruise control or aging prematurely?

Travis Lindquist - Getty Images
MLB 49 43 Baseball's longest contracts 30442524 Adrian Gonzalez: Red Sox, 8 years, $160.3 million Adrian+Gonzalez%3A+Red+Sox%2C+8+years%2C+%24160.3+million MLB

Gonzalez had one year left on his contract, at $6.3 million, when the Red Sox snatched him from the underfunded Padres before the 2011 season. The deal was contingent on a seven-year, $154 million extension that guaranteed Gonzalez an eight-year stretch of Manny Ramirez dollars. Plus, he’s a Gold Glove defender at first base. In August 2012, the Red Sox traded Gonzalez to the spendthrift Dodgers.

Kim Klement - USA TODAY Sports
MLB 49 43 Baseball's longest contracts 30442427 Manny Ramirez: Red Sox, 8 years, $160 million Manny+Ramirez%3A+Red+Sox%2C+8+years%2C+%24160+million MLB

The arms race between the Red Sox and Yankees really took off in 2001 with this signing. Ramirez seemed reluctant to leave Cleveland, but the money talked. As a hitter, Ramirez was a perfect fit in Fenway Park. He teamed with David Ortiz to give the Red Sox the most-feared one-two punch in the game. As a person, Ramirez was a square peg in Boston. His discontent was obvious, and his lack of effort grated on the organization, which once put him on waivers when unable to trade him. There were no takers. Ramirez forced his way out of Boston halfway through the final year of the deal, eyeing his next big contract. Of course, that came after two world championships.

Leon Halip - USA TODAY Sports
MLB 49 43 Baseball's longest contracts 30442522 Matt Kemp: Dodgers, 8 years, $160 million Matt+Kemp%3A+Dodgers%2C+8+years%2C+%24160+million MLB

Kemp got his deal from the Dodgers after finishing second in the National League MVP voting in 2011. After a season of negative headlines, the Dodgers were motivated to make a public statement about the future. Will they regret it in eight years? Kemp has a blend of hitting ability, power, speed and defense not seen since perhaps Ken Griffey Jr.

Mandatory Credit: Jennifer Hilderbrand-US PRESSWIRE -
MLB 49 43 Baseball's longest contracts 30444418 Miguel Cabrera: Tigers, 8 years, $152.3 million Miguel+Cabrera%3A+Tigers%2C+8+years%2C+%24152.3+million MLB

The Tigers acquired Cabrera in a blockbuster trade with the Marlins following the 2007 season and wrapped him up long term the following spring, before he even played a regular-season game with them. In his fifth season in Detroit, Cabrera won the AL MVP and became the first major leaguer to win the Triple Crown since 1967. He hit .330 with 44 homers and 139 RBI as the Tigers won the AL pennant before losing to the Giants in the World Series. Cabrera has been in the top five of the MVP voting four times, while playing with the Tigers. He’s as consistent as they come. The one worry has been his struggles with alcohol. Halfway through the contract, that hasn’t affected his performance.

Otto Greule Jr - Getty Images
MLB 49 43 Baseball's longest contracts 30444427 Alfonso Soriano: Cubs, 8 years, $136 million Alfonso+Soriano%3A+Cubs%2C+8+years%2C+%24136+million MLB

Once traded for Alex Rodriguez, Soriano cashed in big-time, too. The Cubs signed him after the 2006 season, hoping he would be the centerpiece of a new era of success. Soriano did help the Cubs to the postseason in his first seasons in Chicago, but declining offensive numbers have only served to spotlight his defensive ineptitude and indifferent attitude.

MLB 49 43 Baseball's longest contracts 30442429 Mike Hampton: Rockies, 8 years, $121 million Mike+Hampton%3A+Rockies%2C+8+years%2C+%24121+million MLB

It seemed ludicrous when the Rockies shelled out that much after the 2000 season for a pitcher to perform in Coors Field in the pre-humidor days. The critics were proved correct immediately as Hampton’s ERA ballooned to 5.41 in his first year in Colorado. Hampton was gone from Colorado after two seasons and bounced from club to club while battling injuries. Responsibility for the rest of the contract was spread among several teams.

Brian Bahr - Getty Images
MLB 49 43 Baseball's longest contracts 30448588 Scott Rolen: Cardinals, 8 years, $90 million Scott+Rolen%3A+Cardinals%2C+8+years%2C+%2490+million MLB

In the 2002 season, the Phillies sent Rolen to the Cardinals. Later that year, the Cards gave him an extension; the deal included a $5 million signing bonus and a full no-trade clause. Rolen's 2004 season was his best; he ranked among the league leaders in most offensive stats, had the highest vote total of any player for the All-Star Game and finished fourth in MVP voting. A shoulder injury limited Rolen to just 56 games in 2005 and he faced more injury woes throughout his stay in St. Louis. In 2008 he waived his no-trade clause and was shipped to the Toronto Blue Jays. Rolen suffered more injuries there but was able to reestablish his offensive power. In 2009, Rolen was traded to the Cincinnati Reds and was the starting 3B in 2010. Rolen also won his eighth Gold Glove with the Reds.

Gregory Shamus - Getty Images
MLB 49 43 Baseball's longest contracts 30865871 The long haul The+long+haul MLB

When a baseball team hands out a contract of eight years or more, it clearly views the recipient as a franchise player, one it can build around. At the 2011 winter meetings, Albert Pujols landed a monster $240 million, 10-year deal with the Angels. We know he’s a franchise player now, but history shows that’s no guarantee for that to continue for the duration of the contract. We examine some of baseball’s longest contracts, and whether teams received positive return on their investments.

James Guillory - USA TODAY Sports
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