Portland and Miami are not talking.
The conventional wisdom around the league all summer has been that Damian Lillard would eventually get his way and be traded to Miami. The thinking went that the Heat would finally put forward their best offer (which likely includes a third team taking on Tyler Herro) and Portland would accept because they don’t have a better option. That thinking has changed. Portland GM Joe Cronin is pushing to get a trade done and league sources confirmed to NBC Sports that there is momentum building toward a deal, all while the Trail Blazers refuse to engage the Heat. That refusal could be partly because Cronin does not like Miami’s players and picks, but there also could be pressure from above in the Blazer’s organization, or other external pressures, forcing Cronin to find another trade partner.
The “we’re comfortable running it back” vibe coming out of Miami right now is a sign they understand where things appear headed. It’s a negotiation, one call can change everything in a heartbeat, but currently, Lillard does not look bound for South Beach.
If not Miami, who would that trade partner be?
The strongest buzz is around Toronto and Phoenix, something Jake Fischer broke down at Yahoo Sports. This may be in separate deals, maybe in one big one, but the core of the trade (or trades) is Lillard is sent to Toronto, Deandre Ayton to Portland with one or two first-round picks, and Jusuf Nurkic (and likely another role player) to Phoenix. The real key to this entire trade is OG Anunoby, who lands in Portland (he could go to Phoenix depending upon how the deal is structured). The argument for the trade is Toronto wants to take a shot this year with Lillard, Pascal Siakam and an emerging Scottie Barnes, reminiscent of what the franchise did with Kawhi Leonard. Portland fans would argue that landing Ayton and picks is better than the Heat offer, which would be true if Anunoby stays in the Pacific Northwest. (The Ayton part of this deal could well come together whatever happens with Lillard.)
However, Toronto has teased trades of Anunoby and Siakam for a year — and Fred VanVleet and Kyle Lowry before them — only to not go through with the deals. There’s plenty of skepticism around the league this would be the trade they decide to make, mainly because Lillard’s trade request would not go away (he’d ask Toronto to trade him, but he’d show up to training camp and play). Still, there appears to be momentum.
There has been talk of Chicago wanting to be involved, landing Lillard and sending out All-Star Zach LaVine, but that’s harder to envision. Portland isn’t going to want LaVine and his max contract, so a third team has to be brought in, and the Bulls have quietly tested the market for LaVine all summer and found no serious interest (at least at the price Chicago is asking), so who is jumping in as a third team now?
Some fans love the idea of a three-team trade that sends Lillard to Philadelphia, James Harden and Tobias Harris to the Clippers, and a bunch of role players plus a couple of first-round picks to Portland. That trade isn’t happening, however, unless the 76ers change their stance and include Tyrese Maxey (who goes to Portland) and the Clippers change their stance and include Terrence Mann (to Philly), and to say that is unlikely is to dramatically undersell it.
Other teams get mentioned as possible trade partners — New Orleans, Oklahoma City, San Antonio — because those teams have the picks and/or players to make a trade work for Portland. However, none of those teams appear to be seriously interested or engaged.
The cleanest trade for Portland could be straight up with Miami if the Heat put forward their best offer: Two first-round picks (could go up to three), two pick swaps, Tyler Herro, Kyle Lowry, Jaime Jaquez Jr., and Nikola Jovic. Is it the return the Trail Blazers hoped for? No. Maybe the Jazz, Nets or Hornets jump in as a third team to spice things up, but that still could be the best offer. Of course, that has to start with Miami putting this best offer forward (and engaging the right third team), which apparently has yet to happen.
Then Portland has to talk to Miami, and it doesn’t appear willing to. Which is why there’s a growing sense Lillard may not be headed where he wants.