Why Damian Lillard finally asked out and sparked an all out blitz ...

2 Jul 2023

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Damian Lillard - Figure 1
Photo The Athletic

When Damian Lillard finally asked out of Portland on Saturday morning, with his agent, Aaron Goodwin, relaying the word to Trail Blazers general manager Joe Cronin by phone just six days after the three of them had met in person inside his office, there was no mistaking what the seven-time All-Star was hoping would happen next.

It was, as I reported hours before the meeting took place, Miami-or-bust.

But a funny thing happens inside NBA front offices when a player of Lillard’s caliber suddenly becomes available. Executives who had been committed to one plan start considering another. Star players who would love nothing more than to bring “Dame Time” to their arena decide to recruit. They dream big, in other words, scrambling to figure out what it might take to bring one of the game’s greatest players to their town and their team. If there’s any sort of chance at changing his mind, they’re going to try.

And with good reason.

According to a source who has been briefed on the situation, that’s what was happening in those hours after Lillard’s desires were made clear. So while the Heat are still considered the only team that Lillard is truly prepared to play for, there’s a process unfolding that could ultimately lead to other plausible scenarios if the Blazers struggle to find a middle ground with Miami.

Enter Cronin, who made it clear in a statement released Saturday afternoon that he plans on placing the team’s priorities above all others.

“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.”

The list of teams that have interest in Lillard is predictably long, and it’s known to include Philadelphia, the Clippers and Utah. As Bleacher Report’s Chris Haynes reported, a third team would likely be necessary in a deal with the Heat. Miami would likely send guard Tyler Herro to Portland in a possible Lillard deal, but he makes little sense on a Blazers roster that is loaded with guards and would likely need to be re-routed to another team.

Damian Lillard - Figure 2
Photo The Athletic

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While Lillard doesn’t have a no-trade clause like the one that helped Bradley Beal get from Washington to Phoenix recently, there is a common sense component that comes with his massive contract: It would not be wise to trade for a player against his wishes when he’s still owed a combined $216 million. He wants to compete with Jimmy Butler and Bam Adebayo, to grow inside that famed ‘Heat culture’ system under Pat Riley and Erik Spoelstra while becoming the final piece to their championship puzzle. But in the early stages of this latest superstar saga, there are strong indications that Cronin won’t settle on a Heat deal if he doesn’t truly believe it’s what’s best for the franchise.

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While a Lillard deal may not materialize as quickly as the involved parties might hope, it’s worth taking some (Dame) time to better understand the days leading up to his decision. More specifically, what compelled him to finally ask out?

Truth be told, Lillard was ready to ask for a trade Monday. After all those good times in Portland, where the kid from Oakland, Calif., spent the better part of 11 seasons thriving and thrilling in the Pacific Northwest, he was finally ready to say goodbye to the Trail Blazers and hello to a late-career chapter with a true title contender. There was nothing acrimonious or unsavory about their looming split, but Cronin had made it clear at every turn that their priorities were no longer aligned. Not with his words, mind you, but with his deeds.

The Blazers had held onto the No. 3 pick in the draft that had come four days before, taking Lillard’s eventual replacement in Scoot Henderson and ignoring the message he had sent about his desire to use the asset as a way to land another high-level veteran player. According to a source who was involved in the situation, Lillard was still hopeful that the Blazers would find the kind of deal that would make him want to stay. But nothing of substance would emerge.

Yet by the time their meeting inside of Cronin’s office was over, with the GM, Lillard and Goodwin having spent more than two hours trying to find a path forward that made sense for both sides, Lillard decided to wait just a little longer. At Cronin’s request, he would give him a few more days to add to the roster in the kind of meaningful way that would convince Lillard that the Blazers would be competitive at a high level again.

While Lillard didn’t acknowledge the meeting in any way publicly, Cronin released a statement shortly thereafter.

“I met with Dame and Aaron Goodwin this afternoon,” it read. “We had a great dialogue. We remain committed to building a winner around Dame.”

But as the week wore on, there were no updates from the Blazers about significant deals of any kind. From Lillard’s vantage point, the lack of new information about possible trades or updates about ongoing talks surely meant there was no roster momentum to restore his hope. When the Blazers had a quiet first night of free agency, re-signing forward Jerami Grant on a five-year, $160 million deal but failing to add any new players, that was the unofficial end. Then after a late night phone conversation with Blazers coach Chauncey Billups in which they discussed the unfortunate state of affairs, Lillard made up his mind: It was time to leave Portland for Miami.

Or so he hopes.

 (Photo: Steve Dykes / Getty Images)

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