LAS VEGAS -- Portland Trail Blazers general manager Joe Cronin said Monday that a Damian Lillard trade could take "months" to complete in order to satisfy the objective of leaving the franchise in the best possible position if he ultimately trades away one of the best players to ever wear the team's uniform.

"I think what I've learned more than anything is patience is critical," Cronin said in a news conference at Thomas & Mack Center on Monday afternoon. "Don't be reactive. Don't jump at things just to seemingly solve a problem. I think the teams that have ended up in the most positive situations post-trade have been the ones that have been really diligent in taking their time and not been impulsive, or the teams that really kept their urgency under control.

"So I think that's how my approach has been with this and will be with this. We're going to be patient; we're going to do what's best for our team. We're going to see how this lands. And if it takes months, it takes months."

Cronin said he hasn't spoken to Lillard since July 1, when the player asked to be traded, a request that came after an 18-month stretch in which Portland has finished with back-to-back draft picks in the top half of the lottery -- selections Cronin used on a pair of high-upside teenagers: Shaedon Sharpe last year and Scoot Henderson last month.

And although Cronin has said throughout that process that he was trying to find win-now upgrades to build a winner around Lillard, who has spent his entire 11-year career in Portland, he said the answer to the question of "What is the best thing for the Trail Blazers?" was to draft those young players instead of turning those picks into veteran talent.

"Building around Dame has always been the goal all the way, even through the draft," Cronin said. "The difficult things we ran into were finding the right deals. In the previous two years, we drafted at 7, then we drafted at 3. In the meantime, we were scouring the market looking for more win-now players and what kept happening was those players just weren't available. So each time we just tried to weigh that.

"In Shaedon's draft, Pick 7, what does that look like versus what's available on the market? And the answer was obvious: Shaedon's better. And same thing happened this time. What does Pick 3 look like versus the return to the market? It wasn't close. Had to go [making the pick].

"So it wasn't necessarily intentional; it was just doing what's best for this team, and we kept doing that, and I could see why Dame would look at it and say. 'Well this isn't a win-now opportunity as much as, or this isn't as much of a win-now opportunity as some other places. So from that regard, I mean, I understand his position and I respect it and it makes sense to me why he would look to go elsewhere."

And, in looking to go elsewhere, Lillard -- who has four years and over $200 million remaining on his contract after signing a two-year extension with the franchise last summer -- has made it clear that he has only one destination in mind: the Miami Heat, where the combination of Lillard, Jimmy Butler and Bam Adebayo would immediately make the franchise a favorite to, at minimum, repeat as Eastern Conference champion.

"We're going to be patient; we're going to do what's best for our team. We're going to see how this lands. And if it takes months, it takes months."

Blazers GM Joe Cronin, on navigating Damian Lillard's trade request

To this point, however, Cronin has not found a deal suitable to his liking for the future Hall of Fame point guard, who is Portland's leading career scorer and is coming off arguably the best season of his career. But he added that while he cares about Lillard and wants him to be in the best possible position moving forward -- and cited past deals involving CJ McCollum and Josh Hart as examples of seeking the best outcome for both sides, he admitted that having more than one team involved in negotiations tends to lead to better outcomes and that such limited deals are not easy to pull off.

"What the rest of his career looks like matters to us, and we care about that," Cronin said. "At the same time, we have to do what's best for us and we've got to find the right deal and find the right makeup of the team that we're going to go forward with.

"So you hope that you can find that perfect situation where that lines up and he goes to a place that he wants to and you get the best return possible. It's complicated, and usually it doesn't work out just like that."

Although Cronin said he was happy to have retained the services of Jerami Grant and Matisse Thybulle, who both were also introduced Monday after agreeing to new deals with the franchise, the goal was always to try to upgrade the team further through trades. And, although he hoped to have more time to look for deals before Lillard asked on July 1 to be traded, he said he understood why Lillard chose to make the decision he did.

As a result, Cronin admitted that he felt as if he had failed Lillard, from the standpoint that he couldn't get the roster to a place where Lillard could feel it would be competitive fast enough for him to win -- despite Cronin stating his belief that the team's young core of Henderson, Sharpe and Anfernee Simons will be win-now players "very soon."

"I don't feel that I did everything because I wasn't able to get done what we had hoped to get done," Cronin said. "The effort being there, which it was, that's one thing. But actually following through and getting the result is a whole 'nother, and to that extent, I do feel like I failed Dame.

"Our goal was always to build around him and to be as high-level as possible as quickly as possible. And whether, even internally, if we thought, 'Well, hey, we're going in the right direction here, we can get there pretty quickly,' if he didn't feel that, it was still a failure on my end in just not finding that right deal."

And although Cronin has repeatedly said both that he wants to do right by Lillard and that he won't be rushed into making a bad deal, he also said that the goal has always been for Lillard to finish his career where it started -- and that he still holds out hope that could happen.

"I haven't lost hope, just because I understand this league is complicated and things change very quickly," Cronin said. "Sometimes we gain more information. Sometimes things aren't what we thought they were, and it's just something that, in this league, we constantly have to stay nimble and adjust to changing circumstances, and I view it like that.

"I don't know what the future holds. I don't know what will end up happening here. I just know that I won't be surprised if something different happens than we were originally expecting."