Could a Damian Lillard trade to Miami block the Cavs’ path to contention?

CLEVELAND, Ohio — The Godfather sounds more like a grandfather these days.

During last week’s press conference, Miami Heat president Pat Riley explained that he watched Garfield, a popular choice among his grandchildren, when he couldn’t sleep during Miami’s recent playoff run. He joked about issuing a coat-and-tie dress code for Heat coaches (at least people think he was kidding). And like many silent generation survivors, Riley said he struggles to keep up with the 21st century’s 24-hour news cycle.

“All these rumors out there, I’m learning more about this league from you than I’ve ever learned in my life,” Riley shared with a laugh. “I said, ‘How can this happen?’ “

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The scribes laughed, but no one should mistake Riley’s comedy for pleasantries. Between sweet punchlines, the smooth-haired ring chaser made it clear last week that the Heat are still riding his competition bonfire. And his goal this offseason is to build what he considers the fifth iteration of Miami’s championship culture.

The first was built around Alonzo Mourning and Tim Hardaway Sr. Then Dwyane Wade and Shaq Miami won its first championship. Wade, LeBron James and Chris Bosh won two more. And the Jimmy Butler-Bam Adebayo pairing has come close twice in four seasons.

Close has never satisfied the 78-year-old Riley, who famously believes that life contains two crowds: victory and misery. So it’s no surprise that the Heat have once again been linked to disgruntled superstars like Damian Lillard this offseason.

Lillard has always said he prefers to win a title in Portland. But he turns 33 next month, and the Trail Blazers seem hesitant to trade their youth for win-now veterans. Lillard reportedly met with the Trail Blazers on Monday to discuss the direction of the franchise, and he brought agent Aaron Goodwin with him.

Blazers general manager Joe Cronin issued a statement afterward said Portland’s future plans still include Lillard. But that’s lip service unless Cronin can make upgrades that Lillard believes will be able to scratch the same itch Riley described when he told reporters that Miami would not back down from the NBA’s new CBA that penalizes teams for to stack stars.

And that itch makes Miami’s offseason – like Boston’s, Philadelphia’s, Milwaukee’s and New York’s – worth watching in Cleveland.

“He’s committed to doing whatever it takes to fulfill this championship dream,” Riley said of Heat owner Mickey Arison. “It’s been 10 or 11 years, so we’re getting a little anxious here. We want to win another one.”

The ladies’ dance

Athletics Sam Amick reported Monday morning that Lillard has “serious interest” in playing for Miami if — underline, italics, bold face — Portland can’t assemble a championship roster this offseason.

It’s a vague standard to meet, perhaps on purpose. After years of telling the media, he was built different than other, more nomadic superstars, it would take Lillard to leave Portland with grace. He won’t demand or even request a trade. He will simply provide one if/when Portland fails to acquire difference-making talent.

On the other hand, Portland would prefer not to leave this marriage as the partner that didn’t do the job, which may explain Amick’s report that Cronin is “searching the league” for another star player.

Even if that player existed and was available, Cronin probably couldn’t acquire him without trading one or both Shaedon Sharpe and Scoot Henderson. And if Cronin offered those players in trades, Lillard and Goodwin wouldn’t need a meeting to hear about it.

Read here (between the lines): Both parties maintain appearances, but neither believes the other is keeping their mutual agreement. Lillard will say he exhausted the championship court in Portland. The Blazers will say they looked at every conceivable upgrade path.

Still, it seems Lillard will somehow continue his title quest elsewhere.

Women’s destinations

Lillard wants another place to be in Miami, and the Blazers are reportedly motivated to grant his request (again: if it gets there). Amick wrote that Lillard has the same power as former Wizards guard Bradley Beal, who has a no-trade clause because of Lillard’s four-year, $216 million contract.

If so, Miami would have significant leverage in any trade negotiations. The Wizards gave Landry Shamet, Chris Paul (since traded), a bunch of second-round picks, and four first-round pick swaps (at least two of which seem unlikely to convey) in their Beal trade. Portland could encounter similarly unsatisfactory offers if the league knows Miami is Lillard’s preferred landing spot.

In an open market, the Blazers could request Bam Adebayo or — at the very least — Tyler Herro (plus picks) in exchange for Lillard. In this compressed bidding environment, they can receive players like Duncan Robinson and/or Kyle Lowry (plus picks).

But Lillard said in a recent podcast interview that Brooklyn would be another destination he would consider. Lillard likes Brooklyn forward Mikal Bridges. The Blazers should hope Lillard likes Bridges a lot.

Why? Brooklyn owns eight first-round picks between now and 2029, three of which come from the Suns beginning in 2025 (the year Kevin Durant turns 37). Thanks to Brooklyn’s James Harden trade with the Rockets, it doesn’t control its own pick until 2028. So the Nets might be motivated to win soon, which means they might be willing to beat Miami’s low-ball offer — or at least run Lillard’s price higher.

Lillard and Bridges would form a formidable duo in Brooklyn. But the last time Riley acquired three stars, Miami made four straight NBA Finals appearances. Eastern Conference teams like the Cavs need a wild card like Brooklyn.

Miami won the East without Lillard this year. If it can acquire him without sacrificing key contributors, it may be preferable to repeat.

Given the Heat’s track record with undrafted players, no team is better equipped to endure the CBA’s handicap for expensive rosters.

And the playoffs might as well have been a three-month advertisement for Heat culture. Veteran free agents will note the raises that Max Strus and Gabe Vincent are about to earn after impressive playoff runs. And those raises might inspire Strus and/or Vincent’s replacement to take a pay cut, especially if those replacements like beaches and hate state taxes.

The Heat have pulled such heists before during the Heatles era, and the Cavs should be rooting for a sequel. Not just because Lillard, Butler and Adebayo would create matchup problems, but because teams like Miami have long had an even bigger mismatch.

Every time a player like Lillard leaves a city like Portland, it once again underscores a problematic NBA truth. The Blazers – like the Cavs, Pacers or even the defending champion Nuggets – must draft and develop well to build contenders. The Heat – like the Lakers, Warriors or Suns – just need another team to draft or develop poorly so they can call its best player’s agent.

No wonder The Godfather made jokes at the podium. His team is not the punch line.

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