24 (tie). Mark Teixeira – New York Yankees, Major League Baseball:
Following a slugging start to his career with Texas, the Braves, and the Angels, Teixeira signed on for 8 years and $180,000,000 with New York in 2008. The deal averaged $22,500,000 a season, $138,888.89 per game, and included a $5 million signing bonus.
Teixeira won the World Series with the Yanks in 2009. He also hit 39 home runs and 111 RBI in 2011. But he unfortunately went through a long series of injuries from there on out. They sapped him of his skills and he retired in 2016. This deal wasn’t what it could have been.