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At one point in time the big, long and ridiculously money driven contracts in professional sports were few and far between. These contracts were generally only given to the guy everyone considered a “once in a generation” type player. That was until Alex Rodriguez and the Texas Rangers changed the blueprint for long-term contracts in Major League Baseball. Today, contracts of great length and dollar amounts are signed on a regular basis and in lure of the huge contracts signed this off-season, the Roosevelt’s takes a look through history and count down the top 10 biggest contracts in MLB history. Brace yourself; some of these may make you want to change your profession.

Buster Posey: 9 years $164MM

One year removed from breaking his leg in a horrific home plate collision, a collision that changed the rules of baseball, Buster Posey led the San Francisco Giants to their second World Championship in three years. How did he celebrate? By cashing in on a deal worth $164MM over nine years, solidifying him as the Giants backstop until 2022, that’s job security.

Felix Hernandez: 7 years $175MM

Before the start of the 2013 season Felix “The King” Hernandez signed a seven-year contract worth $175MM with the Seattle Mariners. The CY Young award winner will see his salary increase each year through 2019 with a team option for 2020. In 9 big league seasons “The King” has never pitched for a playoff bound team, imagine his stats if he played with Griffey and the boys throughout the 90’s?

Mark Teixeira and Justin Verlander: 8/7 years $180MM

After stops in Atlanta and Anaheim, Mark Teixeira landed himself an eight year deal worth $180MM with the New York Yankees in 2009 – a deal which mirrors Justin Verlander’s seven year 180MM deal with the Detroit Tigers. Teixeira’s contract will reach $22.5MM each year over the last 5 years while Verlander will earn $28MM yearly over the last 6 years.

Joe Mauer: 8 years $184MM

Choosing to resign with his hometown team in 2011, Joe Mauer and the Minnesota Twins agreed to an eight year deal worth $184MM. Mauer, often regarded as one of the best the Major Leagues has to offer behind the dish, will earn $23MM each year of his deal. When Mauer first entered the league he was earning nearly $22.7MM less per year than he does today – think about that.

Derek Jeter: 9 years $189MM

“The Captain” and shortstop for the pinstripes since 1996 signed a well-deserved nine year deal worth $189MM in 2001. The contract, which expired in 2010, saw Jeter lead the Yankees to the playoffs every season, reach the World Series 3 times and won it all in 2009. Often known as one of the greatest of all time, Derek Jeter is that “once in a generation” type of player.

Prince Fielder: 9 years $214MM

One of the biggest players (size wise) in the majors Prince Fielder signed one of the biggest contracts in history with the Detroit Tigers in 2012. A contract that pays $23MM over the first two years and $24MM of the next seven years which will be played for the Texas Rangers . Detroit sent Fielder to the Rangers in exchange for Ian Kinsler this off-season. It seems loyalty to a player and contract lengths don’t go hand-in-hand.

Clayton Kershaw: 7 years $215MM

Los Angeles Dodgers Ace lefty Clayton Kershaw inked a record setting 7 year $215MM contract this offseason. Through the first 5 years Kershaw will make an average of $30MM per year accounting for $130MM in the first 5 years. He then can become a free agent at age 30 or make $65MM over the last 2 years of the contract, hmm the decisions?

Joey Votto: 10 years $225MM

The Reds slugger Joey Votto agreed to a contract extension in 2012 worth $225MM – essentially securing the first base situation in Cincinnati for the next decade. Votto, considered one of the best hitters in the game, already signed an extension in 2011 worth $38MM, meaning in one season he proved to be worth over $180MM more than he had already earned. Good year? We’d say so.

Robinson Cano: 10 years $240MM

Possibly one of the most disputed contracts in MLB history, the Seattle Mariners inked Robby Cano to a ten year deal worth $240MM this off-season. Cano, who everyone believed would play his career in pin stripes, had only one goal this off season -years and dollars not championships and rings. That’s a lot of money for a guy who hasn’t run out a ground ball since Nom.

Alex Rodriguez: 10 years $252MM

The first of two appearances on our top 10 list, or should we say top two list seeing as Rodriguez is in a category all by himself being the only player in history to ink two deals worth over $250MM dollars. The first came with Texas in 2001, (before the steroids that is), when the Rangers landed Rodriguez on a mind blowing ten year $252MM dollar deal. Imagine a $252MM contract isn’t the biggest you’ve ever signed. What a life.

Alex Rodriguez: 10 years $275MM

Coming in at number one on our top 10 list is the before mentioned Alex Rodriguez who signed his second $250+MM contract with the Yankees in 2008. The contract was for ten years $275MM, meaning that since 2001 until the end of his career A-Rod will make a yearly salary of $20MM or more each season. Looks like A-Rod’s bank account has been taking some steroids as well.

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