30 highest career MLB salaries
2. Derek Jeter, $265,159,364
One of the most beloved Yankees in history never came seriously close to reaching free agency, as New York was willing to dish out over $265 million to keep Jeter in pinstripes.
The sixth overall pick in the 1992 draft took a few years to develop, but was eventually considered a top prospect upon his debut in 1995. By 1998, Jeter was a star for a dominant Yankees team, and put up 6.2 WAR to finish third in the MVP voting.
After earning $10 million in arbitration in 2000, the Yankees decided to lock Jeter up for the long-term the next February. New York signed Jeter to a 10-year, $189 million contract to make him the second highest-paid player in baseball.
Jeter was worth at least 4.0 WAR in seven different seasons over the course of the contract and was named to the All-Star game eight times to earn a $51 million extension from 2011-2013. While Jeter was quickly declining at age 39, the Yankees gave him another $12 million for his final season.
With 3,465 career hits, 71.8 WAR and five World Series rings, Jeter was well worth the price tag for the Yankees.