Sure, the team had done their homework on the highly touted prospect and valued his maturity and poise, but they hadn't spoken to him before the draft, let alone worked him out.
With so much misfortune for the franchise ever since LeBron James took his talents back home and with injuries decimating the roster last season, Riley could only smile as he spoke of how Winslow somehow slipped in the draft.
"Good things happen for a reason," said Riley. "Justise was highly thought of by everybody in the NBA. For some reason, he ended up in Miami. Now if we had projected him to be No. 10, we would have locked in on him. He ended up falling to us in a very blessed way. I mean that sincerely. We are so excited about possibly having him with our team for his entire career."
As the 19-year-old sat pensively in between Riley and head coach Erik Spoelstra, two rows of family and friends looked on as the young man was being introduced to a large media crowd at the AmericanAirlines Arena on Monday. Maybe it was a lot to take in, after all he hadn't even picked out his jersey number yet, but his life experiences had taught him to soak in this moment but to never settle and to always strive to work on his game.
"I've had pressure on me my whole life," he said. "It's nothing I can't handle. I sort of think I thrive under pressure."
His versatility and ability to play and defend multiple positions, which Riley and Spoelstra had previously spoken about hoping to draft a player in that vein, makes him a perfect fit to what they want to put out on the court. Spoelstra went even so far as to call him a "Swiss army knife", but it's Winslow's winning mentality that most excites him about his newest player.
"We like players that can play multiple positions, can do multiple things," Spoelstra said. "But more important than that, it's the winning quality, coming from a winning program. Showing an ability to win, even at a young age. I think you can tell a lot about a player during times in the (NCAA) Tournament when you're down and there were some tough moments, you never know when you win until you win.
"But there are some times of doubt, particularly the game against Wisconsin and then all of a sudden, it changes. Winning players rise in those occasions. You can't quantify that with analytics or a statistic. When you see it, you know it. You want to have those kind of players on your team. Justise has proven, in a remarkable way, to have that kind of poise in big moments and find different ways to help his team win. I think that's the most important thing."
Winslow has studied plenty of film, both of himself in an effort to get better and also the greats of the NBA, but isn't interested in comparing himself to others.
"I don't listen to the comparisons," he said. "I watch film on different guys, trying to pull things different guys do. It's about me being me, me playing my game and going out there and performing. I just try to play my game. For me, it's about being myself and that's what got me here."
He does value the fact that people consider his versatility a great asset and he explained that it was born out of necessity.
"I definitely think I'm a very versatile player and it comes from high school," he said. "I played with talented guys but no Tyus Jones' or Jahlil Okafors so I had to learn to do a lot on the court. So that's basically where my versatility comes from. I just like to be a well-rounded player. I showed that at Duke and I'm excited to get better in all areas of my game."
Spoelstra confirmed that Winslow would be participating in Summer League play for the Heat, pointing out that it will be a perfect opportunity for the young man to learn the Heat's culture and system.
While Winslow, Riley and Spoelstra said all the right things today, all three know that the real work begins now.
"I was just really excited to get down here, I know it's a winning organization and (one) that wants to win right now," said Winslow. "That's what I'm most excited about. My whole life I've won, I've been a winner. So to just be a part of an organization that's constantly focused on that and wants to do that and prepares every day to win championships, that's what I'm most happy for.
"That's why when I did get selected No. 10 to the Heat I was so happy. I've just been dreaming about what it would feel like to be here since Thursday night. Now that I'm here, I'm really excited to just be a Heat."