Where Trail Blazers Stand as Franchise-Defining Draft Approaches
The latest intel on the Blazers' draft plans, Damian Lillard's mindset, and the case for Zion Williamson.
Not to be dramatic, but the next 48 hours are among the biggest in Trail Blazers franchise history.
Portland holds the No. 3 overall pick in Thursday's draft and will have the opportunity to select one of either G League Ignite guard Scoot Henderson or Alabama forward Brandon Miller, two prospects that would go first or second in most drafts that don't include Victor Wembanyama.
After Wembanyama officially heads to San Antonio, and Charlotte takes either Henderson or Miller with the second pick, Blazers general manager Joe Cronin will have five minutes to make the biggest decision of his career thus far—keeping the pick or trading it.
Since the disappointing end of the 2022-23 season, the Blazers' messaging both publicly and privately has been consistent: they still plan and hope to build around Damian Lillard, who as of this second is not looking to leave Portland. Last month, the lottery balls bounced in their favor as they moved up from the fifth-best odds to land the third pick in what most executives consider a three-player draft at the top.
The assumption since lottery night has been that Cronin will be not just open, but highly motivated, to move the third pick for win-now help that will keep their window of contention open with Lillard. The same handful of names has circulated around the league, and some of them are more realistic than others.
Mikal Bridges is Lillard's preferred choice and someone the Blazers would strongly consider, but all indications right now are that Brooklyn is not open to moving him. New Orleans badly wants Henderson and has appeared open to discussing Zion Williamson; is that too big of a risk with injuries and off-court concerns for Portland? Boston appears ready to extend Jaylen Brown at huge money rather than taking offers for him. The Blazers have pursued Toronto's O.G. Anunoby in the past, but he's likely not worth the third pick. Anunoby's teammate, Pascal Siakam, is, but he's due for a new deal next summer. Other names that have come up, like Chicago's Zach LaVine and Minnesota's Karl-Anthony Towns, are not players the Blazers—or Lillard—have ever had any real interest in.
There's no trade target, or trade partner, that's a perfect fit without some risk. But keeping the pick is also a serious risk if the Blazers' goals really are what they say they are. Increasingly, Lillard's camp has been making it known behind the scenes that keeping the third pick is not an outcome that will work for them, and that doing so might result in the franchise's all-time leading scorer finally requesting a trade.
I've covered the complicated dynamics around that situation recently—in short, Lillard does truly want to make it work in Portland for the rest of his career, and the Blazers also want him to spend his entire career with one franchise. But Cronin can't make a bad deal involving the third pick as a short-term fix, and if it does come time to trade Lillard, he also can't make a bad deal for minimal return simply to get him to a contending situation.
The Blazers feel they have other avenues to add talent—potentially packaging Anfernee Simons, the No. 23 overall pick and other future picks they can unlock in an agreement with Chicago—and the only player I've heard is completely off the table in trade discussions to add veterans is Shaedon Sharpe. But attempting to walk the line of contending with Lillard while developing talent did not go well last year, and he made it clear at the end of the season that he's not up for a repeat.
Maybe Cronin can do enough to upgrade the roster in other ways that Lillard approves of while keeping the third pick. That will be an easier sell to him if it's Miller than Henderson, due to the positional awkwardness. It's a real gamble, though, that his camp will be willing to wait out free agency before making trade noise if they try to go that way.
You see why the next two days are so crucial?
More and more lately, the Blazers have been signaling to interested teams that they're fully prepared to keep and use the third pick unless they get an offer they'd be crazy to turn down.
Is part of that just a smart negotiating position? Certainly. But there's also real truth to the idea that lottery picks as high as the one the Blazers are holding have never been more valuable than they will be under the new collective bargaining agreement that goes into effect on July 1.
The so-called "second apron" luxury-tax structure that kicks in next summer effectively functions as a hard cap. It will make it extremely difficult for teams to build around three or more highly-paid stars, taking away the mid-level exception and ability to sign buyout players as well as freezing draft picks.
If Portland is paying Lillard what they're paying him ($216.2 million over the next four seasons) while also planning to re-sign Jerami Grant this summer on a new deal that is expected to start around $30 million annually, it's a lot easier to build out the rest of the roster with a potential star like Henderson or Miller on a rookie-scale contract (on the books for just under $10 million next season and a similarly low number for the next three years after that) than it would be to pay someone like Siakam the max-level money they'd command without risking building a team as flawed and top-heavy as what Phoenix has.
That's why, out of all the targets and ideas that have been kicked around in the past two weeks, the one I keep coming back to as potentially making real sense—and having a real shot—is Williamson.
The risk is obvious. So is the reward. Williamson has been legitimately MVP-caliber every time he's been on the court in his career and would be an unguardable pick-and-roll partner for Lillard. He also played just 29 games last season after a hamstring injury, on the heels of missing the entire 2021-22 season with a broken foot. There are long-standing and well-documented concerns about his work ethic and the influence of various family members behind the scenes.
But if you want something that works for everybody—Cronin taking the big, all-in shot he's talked for 18 months about wanting to take, Lillard getting a true superstar teammate to increase the Blazers' competitive ceiling, the organization getting an injection of buzz and excitement after two miserable seasons—Williamson is it.
Complicating all of this is the mystery around what Charlotte will do directly ahead of Portland with the second pick. The intel since lottery night has been that they prefer Miller to Henderson; both prospects met with owner (for now) Michael Jordan earlier this week. It still seems as though they're leaning that way, but it's worth remembering that Jabari Smith Jr. was seen as a lock to go No. 1 to Orlando last year until sudden betting-line movement the night before the draft tipped consensus to the eventual top pick, Paolo Banchero. The only thing we know for sure about this draft is who's going No. 1 to San Antonio. It seems like Charlotte taking Miller next is inevitable, but you shouldn't assume anything until they make it official on Thursday night.
I've also heard whispers that Henderson's people are quietly trying to steer him to New Orleans, because he wants the keys to the offense from day one and doesn't want to split those duties with either Lillard in Portland or LaMelo Ball in Charlotte.
If that is indeed the case, a deal with Portland is the only way that seems viable for the Pelicans. The consistent word out of Charlotte has been that they're not interested in dealing the second pick and want to take a player. But if they were to consider trading the pick to New Orleans, the player they'd want back would be Brandon Ingram, whom Hornets GM Mitch Kupchak drafted second overall in 2016 when he was running the Lakers. The Pelicans, meanwhile, have no interest in moving Ingram, a much less talented player than Williamson but one that doesn't come with the same set of off-court headaches.
The Blazers, by all accounts, feel the opposite from Charlotte. Ingram isn't on the very short list of players they'd view as a true needle-mover worth giving up the third pick for. Williamson certainly is, from a talent and ceiling perspective, but the same issues that have him semi-available from New Orleans in the first place might give them pause.
Nationally, the word for a couple of weeks has been that New Orleans is very open to moving on from Williamson if they have the chance to move up high enough in the draft to get Henderson. A report on Tuesday from Will Guillory, The Athletic's (very good) Pelicans beat writer, called it "fairly unlikely" Williamson gets moved—not exactly a firm denial. The story also detailed the litany of issues between the Pelicans organization and Williamson's camp and underscored that even if he's not dealt on Thursday, the relationship between the two sides will need some repairing. That should tell you a lot.
From Portland's end, the gamble would be that being around Lillard every day will be a good influence on Williamson, and may be the push he needs to start taking his conditioning more seriously. Lillard has dictated the locker-room culture for over a decade, and he has certain well-documented standards players have to adhere to, as well as the credibility to enforce them because he works harder than anybody. The "best leader in the NBA" label he gets is a cliche, but it's also true. If it doesn't work with Williamson here, it won't work anywhere. And the upside of a healthy Dame-Zion duo in a flattened-out Western Conference landscape might be too much to pass up.
The financial aspect of a Williamson move is also a gamble, but there's real upside there, too. He's about to enter the first year of a five-year, $194 million extension he signed last summer, one that includes no player options. He's under team control through 2028 at a salary that starts at a projected $33.5 million next season and tops out at $44.2 million at the end. It's the rookie-scale max (25 percent of the cap), well below the veteran max it would cost to retain someone like Siakam after trading for him. And the five years means not having to worry about the best-case scenario playing out (Williamson staying healthy and dominating) and then him leaving in free agency in a year or two.
The downside risk is that Williamson can't stay on the floor, that contract becomes an albatross and the Blazers have to move on from Lillard at worse value in a couple of years and completely reset. Nobody wants that scenario. But the upside is there in a way that it isn't for any of the other players they could reasonably acquire in a trade involving the third pick.
Another important factor here, and one that should not be overlooked, is that Cronin and Pelicans president David Griffin already have a good working relationship. The biggest trade of Cronin's tenure thus far has been the 2022 deadline deal that sent C.J. McCollum to New Orleans for Josh Hart and future draft picks that he later turned into Jerami Grant that summer. Both sides ultimately came away happy with how that trade worked out, which makes it much easier to envision them working together again. The idea of trying to negotiate for Siakam or Anunoby with Masai Ujiri, famous for his sky-high valuations of his own players at all times, is a lot less palatable.
Cronin has talked since he took over for Neil Olshey as general manager in December of 2021 about liking to take swings. Drafting Shaedon Sharpe last year over a more finished product like Dyson Daniels was a swing that paid off. Signing Gary Payton II as a free agent over other, safer options was a swing that didn't work out. When it comes to star-level talent, all Lillard has ever wanted was for the Blazers to take the swing. Olshey was never willing to take the swing because he couldn't admit defeat on the Lillard-McCollum pairing. Rolling the dice on Williamson may fail spectacularly, but when it comes to swings Cronin could take at this moment, it's the biggest one of all, with the highest upside, at the exact right time to take it.