The ins and outs of why trade negotiations for Damian Lillard, James Harden are moving so slowly

The early rush of free agency is over. Some interesting dominoes are still falling across the NBA, like the Clippers managing to re-sign reserve center Mason Plumlee. As of Monday evening, it appears the next major transactions of this offseason — any solution to the pair of trade requests between Damian Lillard and James Harden — aren’t rushing against the clock and are even stalling several areas of the marketplace.

Trading historic talents in the latter stages of their careers and at large price points is never an uncomplicated task. There’s another common thread between the Blazers’ and 76ers’ current challenges, which various league personnel have labeled a critical reason both Portland and Philadelphia are moving with deliberate pace. Lillard and his representation have made it clear he wants to play in Miami, and Harden has strongly indicated his wishes to play in Los Angeles with the Clippers, so that backs any incumbent team’s front office into a corner. It’s no wonder Blazers general manager Joe Cronin and Sixers president Daryl Morey are conceiving other avenues to move forward, including multi-team trade scenarios.

The dynamic in Philadelphia reads a bit simpler. With or without Harden, so long as Joel Embiid is on the roster, the Sixers are a world spinning around Embiid’s orbit and his aspirations for a championship. The Blazers are deciding where, or whether, to trade a franchise icon and what return that type of move calls for — particularly when you’re so loudly signaling a new era has begun in a small market that’s never been a destination stars like Lillard point to on the NBA map.

Portland Trail Blazers guard Damian Lillard runs up court during the first half of an NBA basketball game against the Phoenix Suns in Portland, Ore., Friday, Oct. 21, 2022. (AP Photo/Craig Mitchelldyer)
Damian Lillard remaining with Portland has put a crimp in some league moves. (AP Photo/Craig Mitchelldyer)

Philadelphia has to consider what next steps optimize its MVP in Embiid, with 22-year-old Tyrese Maxey along for the ride. The Sixers have strongly indicated their combo guard is unavailable in trade conversations, league sources told Yahoo Sports. And so Harden picking up his option forced Philadelphia’s hand, but he’s also now on an expiring deal that — the longer he remains available — some team could decide is worth acquiring for future savings in an even more tax-conscious NBA.

The Clippers, though, do bill as a pragmatic trade partner for the Sixers, far more than the Heat do for Portland’s predicament. Los Angeles has $40.5 million in expiring contracts if Philadelphia wants to become players in free agency next summer, offering a premium landing spot for someone to join Embiid and Maxey just as Harden wants to join Kawhi Leonard and Paul George. For all of the concerns team personnel have about the three seasons left on Norman Powell’s five-year, $90 million deal — which Portland, remember, once hoped would support Lillard’s title chances — maybe the Sixers do ultimately seek Powell in a return from the Clippers and add a trusted veteran into head coach Nick Nurse’s new rotation, having won the 2019 championship together in Toronto.

Lillard’s Miami-or-nothing position is muddying his exit out of Oregon, but under different circumstances. While Harden paced the NBA in assists last season and his pair of 40-point outbursts against Boston helped Philadelphia gain a 3-2 edge in the Eastern Conference semifinals, Lillard was posting All-NBA-caliber performances before his season was shut down. He’s also under contract for four more seasons at over $200 million, quite an expensive gamble for a team owner and front office if there’s no guarantee Lillard will be happy about joining them. If Harden were to get dealt anywhere outside of Los Angeles and raised a stink about not reporting to training camp, it’s far easier to stomach one season of dead money. Then again, Lillard’s sterling reputation of commitment and professionalism also has team executives pondering whether he would truly balk at an unexpected team acquiring the 32-year-old, like when Cleveland landed Donovan Mitchell last offseason.

If Lillard was more open to other destinations than Miami, there’s no question among league personnel Lillard would have a wider market, and Portland would have a much easier process to complete. The Heat’s prominence in this situation makes it unlikely the Blazers will be able to net returns similar to what Brooklyn got for Kevin Durant and the incredible sum Utah received for Rudy Gobert. Miami doesn’t have the consensus blue-chip prospects and surplus of draft capital to send the Blazers. Tyler Herro is an intriguing talent at just 23 years old, but his deficiencies on defense are as glaring as his offensive spark, and his four-year, $120 million contract that begins this season; Golden State just had to pay a first-round draft pick to move Jordan Poole’s nearly identical deal. Brooklyn, which Lillard named as a favorable next team in a recent interview, has the draft assets from February’s Durant deal with Phoenix to blow away Miami’s best possible offer by a wide margin.

For any trade with Miami, Portland would have the goal of moving Herro to a third team, league sources told Yahoo Sports. It seems the challenge for the Blazers with Herro is as much about Portland’s surplus of young combo guards, featuring lottery picks Scoot Henderson and Shaedon Sharpe, plus the high-scoring Anfernee Simons, as it is about Herro’s long-term money. If the Blazers are saying goodbye to the Lillard era in Portland, restarting with another crowded backcourt of small guards with questionable defensive chops isn’t the most optimal launching pad. But finding an additional partner for a Lillard-to-Miami trade hasn’t stopped the Heat from operating as if they’re in pole position to land the superstar guard. It was evident during exit interviews with Heat players, sources said, that Miami was preparing its books for a roster-altering transaction. The Heat have told free-agent players like Malik Beasley, who agreed to a one-year contract with Milwaukee on Monday, that Miami is in a holding pattern before moving forward with its veteran-minimum signings, sources said. Other players like Josh Christopher, recently traded from Houston to Memphis, and Dario Šarić, who had a strong suitor in Golden State, could also be involved with Miami depending on these Lillard proceedings, sources said.

The timing of Lillard’s trade request, one day after the start of free agency and one day after Portland awarded Jerami Grant a five-year, $160 million contract to play alongside Lillard, certainly raised eyebrows across the league. Despite some early speculation around the league, that deal has been agreed upon, and the Blazers plan to honor that commitment to Grant, sources said. Don’t expect Portland to mold that deal into a sign-and-trade either. A large reason why Grant waited for a new deal with the Blazers this summer, as opposed to signing an extension during the season, was Grant’s ability to sign for an additional fifth year, sources said. Grant would not be eligible to sign for a fifth season in a sign-and-trade concept.