Irving had some memorable moments in a Cleveland Cavaliers uniform. It was his three-pointer in Game 7 of the 2016 NBA Finals that served as the knockout punch to cement arguably the greatest NBA upset, as they took out the 73-9 Golden State Warriors.
However, just as the team were beginning to look formidable, the player requested a trade a season after that historic championship.
Irving decided that that situation was no longer for him, so he requested a trade, seeking some of the same power and influence LeBron James had in Cleveland but in a different place.
The 30-year-old, who was 25 at the time of the departure, told I Am Athlete he wished he could've done things differently.
"If I was in the same maturity line and understanding of who I am, and I look back, we definitely, definitely would've won more championships, because there would've been a better man-to-man understanding about what I'm going through," Irving said.
"I didn't know how to share my emotions. I didn't know how to do that. So instead of sharing, I isolated myself.
"I just started pouring myself more into the game - I had one of my better seasons but I wasn't connecting with everybody as much during the championship year. So 2017, it was a different year for us.
"We went against Golden State, we went against a great team. When you're not a great team and not clicking on all cylinders and together, you're easily defeated.
"You're defeated before you can get to the arena. We were in those games against Golden State, but we definitely could've given them a run for their money, regardless if they had [Kevin Durant]."
Relationship with LeBron James
Many assumed that Irving wanted a change because he no longer got along with LeBron James.
While that wasn't solely the case, Irving did not communicate with him while he was going through the trade request process, which he regrets.
"We didn't talk during that time," Irving admitted. "When I look back on what I was going through at that time, I wish I did, because it would've been a good understanding of what the future will hold for both of us and we know how much power we both had together.
"Me and him in the league together running Cleveland, and then being able to put a better team together every single year would've definitely been worth it."