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.

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.

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.

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?
 

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.
 

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.

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.

On Nov. 27, 2012, the Tampa Bay Rays awarded third baseman Evan Longoria with a contract extension that will effectively make him a Ray for life. The agreement with the three-time All-Star incorporated 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 that could make the deal worth $144.6 million over 11 years.

The Rangers shortstop signed an eight-year, $120 million contract extension during Opening Week 2013. The eight-year deal is in addition to the final two years of Andrus’ current contract, giving the Rangers control of the All-Star through 2022. The total package is 10 years, $131.275 million. The deal includes an opt-out clause after the 2018 season as well as a vesting option for a ninth year. But the opt-out clause could, potentially, reduce the team’s commitment to four years, $60 million. The clause is critical for Andrus and his agent, Scott Boras; Andrus likely will opt out if he stays healthy, becoming a free agent at age 30 instead of 34.

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.

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.

Prince Fielder was the subject of much free-agent speculation after the 2011 season, and he finally landed a big contract in January 2012, signing a long-term deal with the Detroit Tigers. Fielder brings some big-time power to Motown, where his father Cecil once also played first base.

On March 29, 2013, the San Francisco Giants locked up their MVP catcher with an eight-year, $159 million extension. He was under contract for 2013 at $8 million, so his total deal is nine years at $167 million, or $18.55 million per year. Posey's contract is the longest ever for a catcher and, at the time, the largest contract in Giants history, beating Matt Cain's $127.5 million deal. In addition, Posey's total guarantee of $167M is a record for a player with fewer than three years of service time, a record for a player with fewer than four years of service time and the largest position-player contract of the 2012-13 offseason.
 

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.

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.
 

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?

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.

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.

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.

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.

On Nov. 30, 2012, the Mets agreed with third baseman David Wright on an eight-year, $138 million contract — the largest in team history. Wright would have been a free agent following the 2013 season.

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.

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.

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.

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.