Five biggest ever MLB contracts

Recent MLB offseasons have been slow. Despite criticism of ownership groups for being reluctant to spend, many of the biggest free agent contracts in Major League history have been handed out in the last few years.

While the stars of the diamond are nowhere near as well-known as Tom Brady or LeBron James, baseball players receive the biggest contracts of the lot. The biggest free agent contracts in MLB history are not loaded with complications like NFL deals, and they are not bound by maximum salaries like NBA.

5 Largest MLB Contracts Ever

Here are the five largest MLB free agent contracts ever, featuring a prominent former Yankee twice.

Bryce Harper – $330 million

The 13-year, $330 million contract handed to Bryce Harper is the largest free agent deal ever. Harper’s free agency was a headline-making topic for months before. Few players, if any, have received the fanfare Harper did as he hit the open market.

Scott Boras took Harper into free agency with history on his mind. The biggest contract in league history was always an aim despite Harper’s performances never quite reaching the level of his spectacular MVP year early in his career.

Harper has a full no-trade clause, but no opt outs. It’s as straight forward as these contracts get – the Phillies’ willingness to go to 13 years is believed to be what pipped the San Francisco Giants, who were in the running for Harper right until he signed.

Gerrit Cole – $324 million

Records toppled when Gerrit Cole signed his $324 million, nine-year pact with the Yankees. It’s the second-longest free agent deal for a pitcher in MLB history, and by far the biggest contract given to a pitcher. The second most expensive deal was signed in the same offseason as the Nationals extended Stephen Strasburg for seven years and $245 million.

A former first overall pick, Cole never realized his potential in Pittsburgh. He leapt from promising young arm to Cy Young candidate in Houston – he’s maintained those standards in the Big Apple.

Cole has received Cy Young votes in each of the last three seasons. He’ll begin the 2021 campaign as one of the MLB betting favorites for the AL award.

Manny Machado – $300 million

Signing just before Bryce Harper, Manny Machado was the first player in MLB history to receive a $300 million contract. Machado was one of the final puzzle pieces as the Padres came out of their long rebuild – he and Fernando Tatis Jr are as dynamic as any infield duo in the sport.

Machado has 40-homer potential. There are few better infield defenders. The Padres are legitimate World Series contenders for years to come and securing Machado on a long deal was a big part of their step from rebuilder to challenger.

Alex Rodriguez – $275 million

Represented by outspoken super-agent Scott Boras, Alex Rodriguez’s free agency was announced during Game 4 of the 2007 World Series. The three-time MVP opted out of the final three years of his deal with the Yankees. The negative response to Boras’ stunt created tension and made it appear Rodriguez’s days donning the pinstripes were over.

Rodriguez showed remorse for how the situation was handled. He built bridges with the Yankees, and eventually broke his own record for the biggest free agent contract in December.

Of course, A-Rod went on to lead the Yankees to their 27th title in 2009.

Alex Rodriguez – $252 million

Not many players get to sign two long-term megadeals. Alex Rodriguez not only got two big free agent contracts, he also landed a pair of historic deals. His $252 million pact with the Texas Rangers back in 2001 was by far the biggest free agent deal at the time at over double Mike Hampton’s previous record.

A-Rod only stuck with the Rangers for three seasons before getting traded to the Yankees. He won an MVP in Texas and two more in New York before his first monster contract was up.

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