The New York Yankees are one of the highest spending teams in Major League Baseball. There are multiple players on the roster who earn in excess of $20 million per season. The highest paid player is Gerrit Cole, making $36 million per season. Following him is Giancarlo Stanton. Thanks to money sent by the Marlins in the trade to acquire Stanton, they technically only pay him $22 million per season. No other players make north of $20 million, including the great Aaron Judge.
Despite their spending relative to the rest of the league in terms of total dollars, they haven’t been able to win a World Series in recent years.