10 Precedent-Setting Blockbuster Contracts

Every year there is a bigger and better contract in the MLB. Free agents, draft picks and other players sign blockbuster deals that become a starting point for later negotiations.

Everything starts somewhere, and at some point a precedent will be set for each situation. Salaries have skyrocketed since baseball began and players continue to rake in the money.

These are a few of the biggest precedent-setting blockbuster contracts in Major League Baseball history.

Andy Messersmith, Los Angeles Dodgers

Free agency was not a part of Major League Baseball until 1975. Before then, players would play under a reserve clause with their team.

Andy Messersmith was one of the first free agents in MLB history. His contract? A three-year, $1 million deal with the Atlanta Braves.

Carl Crawford, Boston Red Sox

Carl Crawford’s seven-year $142 million contract is the richest ever for an outfielder. Unfortunately for the Red Sox, Crawford did not live up to the expectations on a player paid that much.

His underwhelming 2011 stats were lower than those while he was with the Rays the previous season, and was a contributing factor to Boston’s September collapse.

Kevin Brown, Los Angeles Dodgers

Up until 1999, baseball contracts had not yet exceeded eight digits. Cue starter Kevin Brown in Los Angeles.

The then 34-year-old starter signed a seven-year, $105 million contract with the Dodgers. It was the first contract to exceed $100 million. Brown didn’t deliver the way L.A. had hoped. He dealt with injuries after his first season with the Dodgers and was traded to the Yankees in 2003.

His payout paved the way for many other big name players later on.

CC Sabathia, New York Yankees

CC Sabathia is familiar to precedent-setting contracts. He set the record for the largest contract for a pitcher with less than a year’s experience.

Years later, he set another record. His seven-year, $161 million contract is the largest in pitching history, period.

Dave Winfield, New York Yankees

Dave Winfield’s contract with the New York Yankees made headlines for a number of reasons.

The 10-year, $23 million dollar deal in 1980 was the first decade-long contract and the longest at the time.

The contract also sparked a feud, as George Steinbrenner underestimated the overall worth of the contract—including cost of living—when he signed Winfield.

Jayson Werth, Washington Nationals

Jayson Werth’s seven-year, $126 million contract with the Washington Nationals was surprising for a couple of reasons. The length of Werth’s contract meant he would be making $18 million when he was 38 years old.

Werth’s destination also raised eyebrows; the Nationals are a couple years away from playoff contention. The deal upset a number of MLB executives.

Jonathan Papelbon, Philadelphia Phillies

The Philadelphia Phillies made a statement when they decided to sign Jonathan Papelbon. The closer’s recently finalized $50 million contract will go over the next four years with a fifth-year vesting option.

This is the highest contract ever for a reliever. The Phillies’ decision to sign Papelbon to such a large deal could pose a problem later on when it comes to hanging onto starters like Cole Hamels.

For now, though, it set the record, and resulted in the first big-name free agent signing of the 2011-'12 offseason.

Rick Monday, Kansas City Athletics

Major League Baseball’s first amateur draft took place in 1965. The first overall pick of the draft was Rick Monday, an outfielder who went to the Kansas City Athletics.

He signed with Kansas City with a bonus of $104,000, a little under half of Rick Reichardt’s $205,000 record bonus from the year before.

The draft allowed a decrease in signing bonuses, which helped teams be able to compete with their more well-endowed competitors.

Stephen Strasburg, Washington Nationals

Times have changed and signing bonuses have dramatically increased since Rick Monday signed with the Kansas City Athletics.

Stephen Strasburg set a new record when he signed a four-year, $15.1 million contract with the Washington Nationals. His $7.5 million signing bonus became the highest bonus yet.

Alex Rodriguez, Texas Rangers and New York Yankees

Alex Rodriguez was a free agent in 2000. The Texas Rangers finished last in their division the previous season. They addressed their problem by signing A-Rod to a then-MLB highest $252 million 10-year contract. At the time his deal was almost $63 million more than the next biggest contract.

After being traded to the New York Yankees, Rodriguez opted out of that contract to negotiate an even greater deal. He passed up his own record with another 10-year contract, this time for $275 million.

Ally Williams is a B/R MLB Featured Columnist. To contact, leave a note below or follow Ally on Twitter for updates and a constant sarcastic interpretation of the sports world.