How Derek Jeter Made $US265 Million To Become The Second Highest-Paid Player In Baseball History

Alex Rodriguez was at the very top of our list of the 25 highest-paid baseball players in history but Derek Jeter was right behind him having made $265.2 million in his career.

While Jeter is a no-doubt Hall of Famer, he was also a bit lucky to end up making so much, and he’ll retire this year with plenty of money for a very comfortable life.

Let’s take a closer look at how Jeter was the right player in the right place at the right time and made more than a quarter of a billion dollars in his career.

Derek Jeter got lucky right off the bat when 5 smaller-market clubs passed on him in the 1992 draft, including Houston, Cleveland, Montreal, Baltimore, and Cincinnati.

Instead, Jeter was drafted by a team that loves to hand out big contracts. Of the 11 highest-paid players of all time, 8 played at least part of their career with the Yankees.

Jeter also got drafted at the perfect time, playing most of his career with the Yankees under the free-spending George Steinbrenner, but after Steinbrenner's suspension which allowed others to build a contender.

Jeter struggled defensively in the minors, committing 56 errors his first full season. But he eventually got better and was named Minor League Player of the Year in 1994.

In 1996, it wasn't clear if Jeter was ready to be a big leaguer but injuries to the starting shortstop and second baseman from the year before secured his job.


Jeter went on to win Rookie of the year that season and was a key member of first Yankees championship since the 1970s.

Jeter made just $US130,000 his rookie season and $US1.43 million in his first 3 seasons combined.

After winning a second World Series in 1998, Jeter finally cashed in, winning his arbitration case and a $US5 million salary in his first season of arbitration eligibility. The Yankees had offered $US3.2 million.


With 2 years to go before free agency, Jeter agreed to a 7-year, $US118.5 million contract, which would have been the largest contract MLB history at the time.


However, George Steinbrenner didn't want to set the record and when negotiations for $US143 million contract between the Detroit Tigers and Juan Gonzalez fell apart, the deal with Jeter was scrapped.


Instead, after winning another World Series, Jeter and the Yankees avoided arbitration, agreeing to a 1-year, $US10 million contract.

But then Alex Rodriguez signed his record $US252 million contract with the Rangers, so Jeter and the Yankees negotiated a 10-year, $US189 million contract one year before he would have become a free agent.


Even though some argued that Jeter was the best player in baseball, he said it was not important to be the highest paid.


Jeter made $US11 million in the first year of his big deal. But his salary rose steadily, maxing out in 2010 at $US21 million, the highest single-season salary of his career.

Following the 2010 season, Derek Jeter became a free agent for the first time, after having already made $US205.4 million in his career.

However, Jeter never really tested the free agency market and re-signed with the Yankees for $US51 million over 3 years.

Jeter could have activated an $US8 million option this season as part of his old deal. However, the Yankees gave him a 1-year, $US12 million deal which actually helped their luxury tax situation.

Assuming Jeter doesn't change his mind, that brings his career earnings to $US265.2 million.

Now check out the rest of the highest-paid players in MLB history.

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