Pitcher Kevin Brown was baseball’s first player to break the nine-figure barrier, signing a six-year, $105 million contract with the Dodgers in 1999. Two years later, three players cracked $150 million: Yankees captain Derek Jeter (10 years, $189 million), Red Sox left fielder Manny Ramirez (seven years, $160 million) and Rangers third baseman Alex Rodriguez (10 years, $252 million). Deals worth at least $100 million are now so common, we'll limit our look at the active players who have benefited most from baseball opening its vaults — the game's $150 million men.

Source: Cot's Baseball Contracts

Rodriguez hit the lottery twice. In 2000, the Texas Rangers gave him a $252 million, 10-year deal, which was the biggest contract in sports history (nearly $63 million more than the next-richest deal). They then promptly collapsed under the weight of it. Desperate to get out from under the deal, Texas traded A-Rod to the Yankees in 2004. A-Rod, who moved from shortstop to third base when he went to the Yankees, upped the ante again in 2007. After winning his second MVP in four years in New York, A-Rod opted out of his old deal and negotiated a new contract (without his agent Scott Boras) with the Yankees for 10 years, again setting a record for the biggest contract in baseball history.

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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 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 and Votto became the third first baseman in four months to eclipse the $200 million mark, following Albert Pujols and Prince Fielder. His average annual salary is $22.5 million.

The Detroit Tigers came out of seemingly nowhere to sign prized free agent Prince Fielder in January 2012. Fielder, 27, had been a rumored target of many teams before the Tigers swooped in and made him baseball's third $200 million man, behind only the Angels' Albert Pujols and the Yankees' Alex Rodriguez.
 

Was that really small-market Minnesota spending money like the Yankees? Well, when you have a homegrown All-Star who catches and leads the league in hitting, you mortgage the farm to keep him. The Twins extended him through 2018 after he was named the 2009 American League MVP. The pride of St. Paul struggled in 2011, as did the Twins.

The Yankees nabbed the prized free agent of the offseason in December 2008 when they signed Teixiera, who was coming off a solid second half with the Angels. One of the best first basemen in the game, Tex led the American League in homers (39) and RBI (122) in 2009 and helped the Yanks to another World Series championship.

The Yanks play with Monopoly money: Sabathia wasn’t even the only $150 mil deal they handed out in their 2008 offseason spending spree — Mark Teixeira also passed Go and collected $180 million. The Yankees needed a new ace, so they made Sabathia, the 2007 American League Cy Young Award winner, the richest pitcher in history. He went 19-8 in 2009, was MVP of the ALCS and helped the Yanks to another World Series championship. He won at least 19 games in each of his first three seasons in New York. Wise investment.

After the season that their center fielder had in 2011, the Dodgers weren't about to let him get away. The team and Kemp agreed to an eight-year, $160 million extension. The Dodgers suffered through ownership woes all season and, after divorcing wife Jamie and having MLB step in to run the team, Frank McCourt was finally forced to sell the team. Kemp was one of the few bright spots during an otherwise forgettable year: He hit .324 with personal highs of 39 home runs, 126 RBI and 40 stolen bases. His .586 slugging percentage and .986 OPS were also career highs. Kemp has produced 128 homers and a .294 batting average in 787 career games. He is also a two-time Gold Glove winner. At the time of the extension, Kemp had one season left on a contract that paid him $7.1 million in 2011.

The Rockies like to lock up their stars for a lifetime. Seeing as how Tulo will be close to 37 when his contract with Colorado expires, the Mile High City could very well be the only baseball home the shortstop ever knows. The Rockies — who also signed stars Carlos Gonzalez and Jorge De La Rosa — are counting on all these long-term investments to pay off with future postseason success.

The Boston Red Sox agreed to a seven-year, $154 million contract extension with their star first baseman on April 15, 2011, after acquiring him in December from the Padres. The extension will take effect in 2012. The deal completed an expensive four-month period for the team, which included a seven-year, $142 million contract for free-agent left fielder Carl Crawford. The Red Sox waited until after Opening Day to formalize the Gonzalez agreement in an attempt to avoid Major League Baseball luxury-tax fees for 2011. 

The Tigers landed the biggest Marlin at the end of 2007, acquiring the slugger in another Florida fire sale. The Venezuelan first baseman led the AL in homers in 2008 and has averaged 35 homers and 115 RBI in his four years in Detroit.