5. Striking out on Damian Lillard
The most painful regret during the last five seasons will be not getting the job done in bringing on superstar guard Damian Lillard.
Last summer, the former Portland Trail Blazers franchise player requested a trade to the Heat, and specifically only the Heat. After a summer-long drama of talks between Miami and Portland that went nowhere, Lillard finally ended up with the rival Milwaukee Bucks.
Heat insiders mentioned over the years that because the team is so limited financially and asset-wise, the only way of acquiring a star in a trade is if they demand Miami as their top destination.
Well, that opportunity finally happened, and Riley still wasn’t able to get the job done. It was speculated that the Heat front office assuredly wanted Lillard’s services, but it seemed like they tried to get away with low-ball offers until it was too late. Riley’s negotiation tactics rubbed Trail Blazers general manager Joe Cronin the wrong way.
In what could have been the last realistic chance of pairing Butler and Adebayo with another true superstar to round out a new trio, the Heat may have fumbled this one. Lillard’s arrival would have instantly elevated Miami to East favorites and provided the team with someone who could maximize this title window. Instead, the Heat missed out, found themselves in the play-in tournament for the second straight season and won just one playoff game.
Now Butler will return for another season without a new contract and plans to enter free agency next summer. That means this could be the Heat's last chance to punctuate the Butler era with a championship.