It's almost befuddling to the mind that one of the masterminds behind the formation of the "Big Three" would have a few red marks on their record. He got help from Dwyane Wade along the way, but flashing a few rings and possessing the aura of being an NBA legend as a coach and as a member of front-office personnel certainly did their part in convincing LeBron James and Chris Bosh to play in Miami.
Outside of Phil Jackson, there wasn't a personnel member in the NBA that had the resume Riley could boast. He was a winner as a player as a member of the champion 1972 Los Angeles Lakers and as a coach for four Laker titles during the Magic Johnson era throughout the 1980's and a Heat title in 2006.
There isn't much else that comes to mind when you think of Riley besides winning. Everything he has touched has turned to gold and nobody knew that more than Wade, James and Bosh. They instilled their trust into Riley by sacrificing money and individual statistical achievement and it's resulted in an NBA title and possibly another one on the way.
Riley, however, is nowhere near perfect. Nobody is. Even Jackson ended his career succumbing to a sweep and even Riley was briefly a part of the Heat team that won 15 out of 82 regular season games.
There have been several decisions over the course of Riley's tenure with the Miami Heat that have been deemed as questionable, especially when it comes to his drafting. In between Dwyane Wade being drafted in 2003 and Norris Cole in 2011, the Heat have held on to not one of their draft picks simply because they were not worth holding onto.
That's not just because the Heat were selecting late. They have waved goodbye to former picks that range from the second to the 19th to the 20th.
Just consider those failed picks as a silver lining. Because without those failed picks and poorly thought-out moves, the Heat probably wouldn't be in the position where they are as the Eastern Conference's current number one seed with a 41-14 record.
Here's a look at Riley's five worst decisions in his time with the Miami Heat.