Damian Lillard Rumors: Heat Prepared for Trade 'for Several Months, If Not a Year'

The Miami Heat's pursuit of Damian Lillard has reportedly been a long time coming.

ESPN's Brian Windhorst said the Heat have been preparing to make a run at Lillard for several months, if not longer.

"Very clearly Dame Lillard wanted to give the Blazers every opportunity and very clearly the Blazers didn't want to take the opportunity because they haven't done anything to improve their roster, literally nothing. So, I can understand why Dame is saying that, so we know that Dame's preference, very clearly also, is Miami. And Miami has been preparing for this situation for several months, if not a year," Windhorst said Monday on Get Up.

"Now, the trade that the Heat have to offer, which largely centers around draft picks and Tyler Herro, obviously also isn't really what the Blazers are looking for. And so, now we begin the game. And I'll say, we watch NBA stars do their thing in May and early June every year, well late June and July is where the NBA's front office stars do their thing. And this is what we have going on right now, is the front office stars of the NBA rolling up their sleeves and trying to make a deal for Dame Lillard. You have the Miami Heat with Pat Riley and Andy Elisburg, who have made a dozen or more of these types of star trades over the last 25 years. You have Daryl Morey and Elton Brand in Philadelphia, also veterans of many big deals rolling up their sleeves and seeing if they can flop a James Harden trade into a three-team trade that gets them Dame Lillard. Plus, some other teams lurking out there with other front office stars and veterans of big trades, like maybe Danny Ainge in Utah. And so, we will watch this play out behind the scenes in the coming days to see who wins this sweepstakes."

Miami's actions during the early free-agency period certainly hint at the team having a major move in store. The Heat allowed Max Strus and Gabe Vincent to walk in free agency and also traded Victor Oladipo to the Oklahoma City Thunder for no return, creating a trade exception in the process.

While Josh Richardson and Thomas Bryant signed contracts with Miami, both are coming for the veteran's minimum. The Heat front office is seemingly determined to keep their maximum financial flexibility in order to make a blockbuster trade—most likely for Lillard.

The All-Star guard officially informed the Blazers of his trade request Saturday, saying Miami is his preferred destination. This came as no surprise to anyone who has followed the Lillard saga, with Dame previously highlighting Miami as an intriguing option.

"Miami obviously," Lillard told The Last Stand podcast when asked where he'd like to play if not in Portland. "Miami is the obvious one, and Bam (Adebayo) is my dawg. Bam is my dawg for real. Miami is the obvious one."

While the Blazers are expected to accommodate Lillard's trade request, there is no guarantee he'll wind up in Miami. General manager Joe Cronin said the team plans to only act in the best interest of the franchise.

"We have been clear that we want Dame here but he notified us today he wants out and he'd prefer to play someplace else," Cronin said in a statement. "What has not changed for us is that we're committed to winning, and we are going to do what's best for the team in pursuit of that goal."

Lillard has spent his first 11 seasons in Portland, emerging as arguably the greatest player in franchise history. He had been consistent in his desire to retire with the Blazers, but the front office has steered directly into a rebuild in consecutive seasons.

Portland started its rebuilding process in February 2022 by jettisoning a swath of veteran talent, including guard CJ McCollum, and then doubled down by taking Shaedon Sharpe in the lottery rather than trading the No. 7 pick for a veteran. Despite Lillard publicly saying he did not want to sit through a youth movement, the Blazers again stuck to their guns in this year's draft, taking Scoot Henderson—a point guard—with the No. 3 pick.

Once it became clear the Blazers were passive-aggressively moving on, Lillard seemingly decided to up the ante and ask for a divorce.