24 (tie). Justin Verlander – Detroit Tigers, Major League Baseball:
Verlander re0signed with the Tigers, the team that drafted him in 2005, He re-signed with the team for 7 years and $180,000,000 before the 2013 season. His contract was the biggest in MLB history for a pitcher at the time. It averaged $25,714,286 per season and $158,730.16 per game.
Verlander was worth it even though he had a pair of mediocre years in 2012 and 2013. Following his big 2011 season, he was the second pitcher in history to win all three of the Rookie of the Year, Cy Young, and Most Valuable Player awards. He was the Cy Young runner-up in 2016. The Tigers traded him to the Houston Astros for three players at the trade deadline in 2017. He was the American League Championship (ALCS) MVP and promptly helped the Astros win the World Series that year. Whatever he got paid, he earned it.