When LeBron James left the Miami Heat for the Cleveland Cavaliers, the camp of Chris Bosh wanted to reopen a deal they had just finished. Bosh's camp knew the Heat had extra money available.
Bosh threatened to sign with the Houston Rockets but ultimately signed a five-year, $118 million max contract.
Wade signed a two-year deal with $15 million in 14-15 and $16.125 million in 15-16, which allowed the Heat to sign Luol Deng. Wade opted out and re-signed a one-year, $20 million deal for 15-16, but was unable to come to terms with the Heat in 2016 and signed with the Chicago Bulls.
Bosh, meanwhile, hasn't played for more than a season due to recurring blood clots.
Riley now wishes he would have said no to Bosh's max deal and given all of that available money to Wade.