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Richest Contracts In Team History: AL East

Salaries are going higher and higher. Who has the AL East Richest Contracts? With the Yankees and Red Sox competing, it’s a heckuva list.

I look into how the Yankees have dominated behind super star pitching, and incredible hitting.

With all of these big contracts being dished out to free agents, it got me thinking. What are the richest contracts in every team’s history? Whether it is a free agent signing or an extension contract, all count here. We have seen decade-long deals being signed recently. So with that being said, let’s check out the richest contracts in team histories. First up, here are the AL East Richest Contracts.

Toronto Blue Jays

Largest free-agent deal: George Springer, OF (six years/$150M, 2021)

Largest contract extension: Vernon Wells, OF (seven years/$126M, 2007)

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The Blue Jays had not dished out a big contract in a while. In 2021, Toronto made a splash in free agency by signing George Springer upping their chances in the AL East. Springer signed a six-year, $150 million deal, the largest total value deal in Blue Jays history. The original record was held by Russell Martin’s $82 million deal.

The Vernon Wells deal never saw Wells as a Blue Jay throughout the entire deal. Wells extension was slated to run through 2014 but he was traded to the Angels in January 2011 and to the Yankees in March 2013.

Tampa Bay Rays

Largest free-agent deal: Wilson Alvarez, LHP (five years/$35M, 1998)

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Largest contract extension: Wander Franco (11 years/$182M, 2022)

Next up is the Tampa Bay Rays. The Rays are another team in the AL East that has not been very active as far as “big money deals”. The last time a free agent deal was done in Tampa was in 1998. Funny enough, when Alvarez signed his deal, the Rays had not played a game as a franchise yet. The average annual value of his deal has been beaten many times by other Rays free agents, but not the total value.

As far as extensions go, Wander Franco has the largest deal in Rays history. Franco’s deal includes a 12th-year club option and can max out at $223 million. This deal is far and above the previous record held by Evan Longoria’s six-year, $100 million extension signed following the 2012 season.

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Baltimore Orioles

Largest free-agent deal: Chris Davis, 1B (seven years/$161M, 2016)

Largest contract extension: Adam Jones, OF (six years/$85M, 2012)

Up next is the Baltimore Orioles and they also have not been active in big-money deals. Back in 2015, Orioles first baseman Chris Davis led the majors with 47 home runs. Davis had been with the Orioles for four years but decided to test free agency. However, he ended up back in Baltimore on a seven-year, $161 million deal.

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As far as extension contracts, Adam Jones takes the record after signing a six-year deal during the 2012 season. Jones actually lived up to his contract after signing considering he finished sixth in AL MVP voting. Jones was one of the best players for Baltimore during the early 2010s.

Boston Red Sox

Largest free-agent deal: David Price, LHP (seven years/$217M, 2016)

Largest contract extension: Adrián González (seven years/$154M, 2011)

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The Boston Red Sox have two of the highest AL East Richest Contracts. Next, we have the Boston Red Sox and they have been far from inactive money-wise. Their most recent deal was signing former Rockies shortstop Trevor Story. Story signed with Boston on a six-year, $140 million deal. But that deal is far from the record in Boston by a free agent.

David Price signed a seven-year, $217 million deal and at the time, Price’s deal was the largest by total value for a pitcher. However, he didn’t even play out the whole contract in Boston following a February 2020 trade to the LA Dodgers. Speaking of the Dodgers, the largest extension deal for Boston, given to Adrian Gonzalez, also was not finished in Boston as he was traded to the Dodgers in 2012.

New York Yankees

Largest free-agent deal: Gerrit Cole, RHP (nine years/$324M, 2020)

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Largest contract extension: Derek Jeter, SS (10 years/$189, 2001)

We finish up the AL East Richest Contracts with the big money spenders in the division, the Yankees. With their insane budget every year it is no surprise they have the largest deals. Cole’s contract set plenty of records, including the most total value on any contract for a pitcher and the highest average annual value on any contract at $36 million. However, Cole’s annual value is now second all-time behind Max Scherzer ($43.3 million per year). Cole’s contract is the third-highest free-agent deal in MLB history.

As far as extension contracts go, this is my favorite one. Derek Jeter signed the 10-year, $189 million deal to ensure he stayed a Yankee his whole career. Jeter obviously played out that entire extension before hitting free agency. However, he signed one final one-year deal and retired after that season in 2014. Derek Jeter’s extension is still the 10th highest extension deal in MLB history.

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An honorable mention here would be the 10-year, $275 million contract Alex Rodriguez signed in 2008. A-Rod was already playing on a 10 year, $252 million deal he got from the Rangers. He only played the first three seasons of that deal before he was traded to the Yankees. Once he got to New York, after a few years, he decided to opt-out of the final three years of that Rangers deal that carried over and renegotiate. His new $275 million deal became the richest free-agent deal in MLB history at the time and to this date is the sixth highest in MLB history.


Want more MLB content? Check out our website here and check the website for the next divisions highest contracts!

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Written By

Born and raised in Independence, MO, 24 years old. 2020 Bachelors Degree in Sports Media from Northwest Missouri State. Sports nut who enjoys bringing information and entertainment to the public!

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