What is the biggest contract given to a Yankees’ player?

Yankees started the era of big player contracts in baseball.
Inna Zeyger
Tuesday December 13, 2022

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The $360 million, nine-year deal given to Aaron Judge is the biggest ever contract the Yankees have given to a player. The Bronx Bombers spend more money than any other sports team. Since the era of George Steinbrenner, they are known to splash big to put together a team with many of the best players from other teams.

But the Yankees are being unusually quiet about free agents right now. With a few exceptions, the team decided that developing players over time was a better way to save money than buying complete players at crazy prices. However, this offseason, one of these exceptions took place. They gave out their biggest contract to date.

Before Aaron Judge, Gerrit Cole had the biggest Yankees contract ever. The former Houston Astros ace Gerrit Cole got a nine-year, $324 million deal in New York. Though it is just a little bit less than Giancarlo Stanton‘s $325 million contract, Cole gets more money each year.

Giancarlo Stanton still remains the second most expensive player for the Yankees if we consider the total value of a contract. The Yankees have to pay this huge amount, it’s because the Miami Marlins left it to them. This amount has to be paid back over 13 years, which started in 2014 for the Marlins.

Before Cole’s big deal, the biggest contract a Yankees starting pitcher had $155 million given to Masahiro Tanaka in 2014.

However, it was Alex Rodriguez’s contract of $275 million with the Yankees in 2007 that broke all MLB records.

Alex Rodriguez‘s contract is a great example of the kind of deal the Yankees were known for. When he signed a huge deal with the Rangers for $252 million, the record deal broke many hearts in Seattle. But it didn’t last long. Rodriguez chose not to play in Texas and moved to New York in 2004. The Yankees handed him “a new 10-year, $275 million deal” after a big-hitting performance for two years.

His $275 million will be around $390-400 million today. Overall, Rodriguez delivered. Even though he was suspended for using drugs to improve his performance, the 14-time All-Star earned his money. But it might not be a coincidence that after the A-Rod/Derek Jeter era, the Yankees moved away from their usual style of putting free agents up upfront.

Yankees’ George Steinbrenner changed baseball by splashing big

Before 1973, baseball contracts were pretty stable because most people didn’t want to pay a lot. Curt Flood fought for players to be able to choose which team to sign with. But the really big contracts didn’t start coming in until after 1973 when George Steinbrenner bought the New York Yankees. Steinbrenner was much less cautious about how he signed players. He knew that the team’s already good income could be made even better by winning more games and getting the most talked-about players he could find.

For decades, the Yankees gave some of the best baseball players contracts that got bigger and bigger. He brought Reggie Jackson for $2 million, Catfish Hunter for $3.5, and broke all record books in 1980 by signing “Dave Winfield to a 10-year, $23 millon contract.” In just a few years, the Yankees, led by Reggie Jackson, won back-to-back World Series.

In the short term, this strategy costs a lot of money, but it turned Steinbrenner’s $10 million investment in the team into a multi-billion dollar business. This strategy didn’t always work, especially after modern analytics made it possible for cheap players signed before free agency to turn smart teams into contenders for the playoffs.

Under Hal Steinbrenner, George’s son, the Yankees are more careful about who they sign. When he had the chance to add an expensive veteran ace to his young, talented team, he didn’t take it.

What do you think the Yankees’ big-spending habit? Leave a comment below.

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