#5 Stan van Gundy - $7 million
With a 37-year background as a basketball coach, Stan van Gundy has indeed been associated with the sport at a high level for most of his life. van Gundy's journey in the NBA began with the Miami Heat organization, who recruited him as an assistant in the 1994-95 season.
9 years into his job, with the position left vacant following a season spent tanking to obtain generational talent, the Heat promoted him to the head coaching position in 2003. In his first season in charge, the Heat made the playoffs once again, making it to a second-round loss against the league-leading Pacers.
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van Gundy made the All-Star game as a head coach the following year, but the acquisition of Shaquille O'Neal had made Miami a real contender. This tempted Riley into coveting the head coaching job, and midway in the 2005-06 season, van Gundy resigned. His next job was with the Orlando Magic, whom he led to the 2009 NBA Finals and the 2010 Eastern Conference Finals building his roster around Dwight Howard.
van Gundy earned his major paycheck in his last job, which was as a president-cum-head coach role for the Pistons until the end of last season when he was fired.
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