Editor's note: This article was originally posted on June 27 and was updated after Damian Lillard officially requested a trade on July 1.
It is the NBA offseason, AKA Damian Lillard trade rumor SZN. If you've been on the internet over the last week you know why this article is being written. Lillard is 32 years old and coming off his best season. The window for him to win a championship as the central player on a roster is rapidly closing. The Portland Trail Blazers, knowing this, still selected Scoot Henderson in the NBA Draft last Thursday instead of flipping him or the pick for a veteran player capable of helping drive the team to championship heights this season.
This sequence of events feels like it is paving a road to Lillard finally asking the Blazers to trade him. The superstar point guard probably has "loyalty" literally tattooed on his body somewhere given how often he talks about it, but the Blazers simply are not going to push all their chips into the middle right now. The latest report from Brian Windhorst on Tuesday claims Lillard wants to wait and see what Portland does in free agency before doing anything drastic.
That's all well and good but the Blazers are going to struggle to do much in free agency. Their cap sheet is pretty loaded already and that's before they presumably attempt to re-sign Jerami Grant. Once they do that the best thing they can do is trade Anfernee Simons and/or Jusuf Nurkic, who have very different values but share the common trait of other teams knowing the Blazers want to move them. So finding a good deal might already be off the table and Portland will seriously consider rolling into next season with largely the same roster plus Henderson.
That is both the likeliest outcome and the most undesirable for Dame. Unless the Blazers pull off something crazy, Lillard becoming unhappy with the direction of the team seems inevitable. Thus, let's break down the teams who could possibly make a move for Lillard if it comes down to a bidding war.
UPDATE: Lillard officially asked out on July 1, per Chris Haynes.
Lillard does not have a no-trade clause but the Blazers are almost certainly going to adhere to his wishes if he asks to be traded to a specific team. And Lillard has reportedly asked to be traded to the Heat already. So they are the front-runners.
This works out because Heat were kind of all-in on Lillard by now anyway after letting Gabe Vincent and Max Strus both walk out the door with no real compensation. They need him Lillard if this offseason isn't going to be a disaster. A deal will start with Tyler Herro's $27 million salary and go from there. It will definitely include a plethora of picks from the Heat (including their 2023 first-rounder Jamie Jacquez Jr.). And that is pretty much all we know for sure. The bet is that the Heat will try to get a third team involved so that the Blazers get some more assets because Herro, Duncan Robinson, and Jacquez or Nikola Jovic with picks isn't going to get it done.
During the same podcast we mentioned above Lillard also revealed he's pals with Mikal Bridges and wouldn't mind playing for the Brooklyn Nets. Coincidentally, those same Nets are in a position where it would actually make sense to burn all the assets they got in the Kevin Durant and Kyrie Irving trades for Lillard because they owe their own draft picks to Houston. The picks Brooklyn does own are actually pretty valuable given they come down the road from the Suns and Mavs, both of whom are teetering on the edge of disaster for different reasons in 2023 and may be entirely in the hole by 2027 or 2029.
Brooklyn has also been fairly quiet so far this offseason. They kept both their first-round picks and used them on Noah Clowney and Dariq Whitehead, which are intriguing young prospects to dangle in a Lillard trade. They did send away Joe Harris to the Pistons, which takes his contract out of the running to help make the money work, but that part of the deal isn't difficult with Ben Simmons still on the roster. A trade featuring a bunch of those aforementioned picks, the two rookies, and Simmons' contract is a great starting point. The sticking point will likely be Nic Claxton. If the Blazers want him (and they should) then it might be hard to come to terms on a deal. But if he ends up the centerpiece and the Nets get to keep Clowney, we might have something to work with here.
The 76ers have their own point guard they are trying to trade after the James Harden situation came to a very unlikely end. Harden opted into his $36 million player option and both sides want him to play in a different uniform next season. Trading Harden for Lillard wouldn't work in any manner; financially other pieces would need to be included and the Blazers absolutely want more than that. But there is a way for this to work out in Philly's favor.
If the Clippers are still interested in Harden, then sending him to LA and getting Lillard to Philadelphia is made fairly easy money-wise. Tobias Harris would have to be involved but the combination of his contract and the mid-sized deals the Clippers have in bulk will be able to match Lillard's huge deal. Something like Harden to the Clippers, Lillard to the 76ers, and then picks from those two teams along with Harris, Tyrese Maxey, Norm Powell, and whatever young guys the Blazers want from the Clippers would make sense. Philly would love to land Dame without giving up Maxey but that doesn't seem likely. Maybe a fourth team that actually wants Harris could get in on the action and send more picks or useful young guys to Portland. There is a lot to work with here-- the question is if the pieces can get lined up in time before a simpler trade comes to fruition.