How Trail Blazers Can Unlock Draft Picks to Make Blockbuster Trade
Portland wants to go all-in for a star. How can they trade future picks? It's complicated.
Joe Cronin has made no secret of his plan this summer to make the kind of splashy star acquisition that would vault the Trail Blazers from the lottery team they were the past two years into the contending conversation.
Over the next few months, the Blazers—and the rest of the league—will get a better idea of which of those types of players are available in trades. One thing's for sure: no matter who it is they target (I have some guesses, but they're just guesses at this point), it's a lot easier to get that kind of trade done if you have draft capital to play with.
Last summer's three blockbuster trades all involved significant picks changing hands. Utah got four first-round picks plus a swap from Minnesota for Rudy Gobert and three firsts and two swaps from Cleveland for Donovan Mitchell, while San Antonio got three first-rounders plus a swap from Atlanta for Dejounte Murray. At the deadline, Phoenix sent Brooklyn four first-round picks plus a swap and two second-rounders for Kevin Durant.
That's the market for those sorts of trades these days, and the Blazers have some work to do to get there. In the summer of 2021, then-general manager Neil Olshey traded a lottery-protected first-rounder to Chicago along with Derrick Jones Jr. as part of the three-team deal that sent Lauri Markkanen to Cleveland and Larry Nance Jr. to Portland. The lottery protections on that pick last through 2028, at which point it becomes a second-rounder, and the Blazers are limited in how they can trade picks until it conveys.
It is possible for Portland to work out an arrangement with Chicago to send them another asset as incentive to change or lift those protections, and it's something they've already discussed.
"Chicago and I talked during pretty much every transaction window," Cronin said in February at his post-trade deadline media availability. "'Hey, if it ever becomes necessary, would you be open to this?' We kind of laid a real light foundation of, 'We'll call you if things heat up.' That kind of thing, but basically trying to tee that up in case we have to hurry. It's negotiable, it's whatever we work out."
There are many different ways they could resolve the situation. It could be very simple, or it could get complicated.
The cleanest way for the problem to be solved involves the No. 23 overall pick that the Blazers got from the Knicks in the Josh Hart trade at the deadline. If the Bulls are open to it, Portland could simply offer them this pick for their own pick back. Chicago is highly leveraged in the future picks they owe stemming from the Nikola Vucevic and DeMar DeRozan trades, so they'd likely accept this. The Knicks pick is roughly equivalent to the pick they would have gotten from the Blazers if it had conveyed this year. The Bulls get a mid-first-round pick, Portland doesn't have to worry about restrictions on their own future picks anymore, they wash their hands of the problem. Everybody's happy.
But it's not a lock that's what happens. Cronin may want to keep that Knicks pick, either to use in another trade or to draft someone in the middle of the first round. If they don't do anything with the Bulls to change the situation on the future picks, having the Knicks pick allows the Blazers to trade their own lottery pick this year before the draft while still satisfying the Stepien rule. And unless they win the No. 1 pick and the opportunity to draft Victor Wembanyama (a 10.5 percent chance), trading their own pick feels like the most likely path to adding the kind of win-now talent they need to put around Damian Lillard.
There are other options outside of the Knicks pick when it comes to working something out with Chicago.
For one thing, after their deadline moves, Portland now has a surplus of second-round picks to play with. They don't have their own second-rounder this year, but they have Atlanta's pick, which is slated to be No. 43 overall. In total, they have six current or future second round picks, both their own and from other teams, with varying levels of protection (the entire rundown is here). They could offer the Bulls a handful of those in lieu of the Knicks first-rounder, if Chicago would take that as a return to give them back their own pick. They could also offer the Bulls a player, but that's less likely.
They also don't have to just trade for their own pick back outright. One option would be to come to an agreement with Chicago to change the length of the protections. As it stands right now, if Portland misses the playoffs every year between now and 2028, the Bulls would ultimately receive a second-rounder instead. They could agree to change the end date and make the pick lottery-protected through, say, 2024 or 2025, and give the Bulls an extra second-rounder or two for being willing to shorten it.
If that happens, it could open up future picks sooner. Changing the final year of the protections to 2025 would give Portland the ability to then trade its picks every other year starting in 2027, plus swaps in the years in between.
Even as things stand right now, there are still things Cronin can do when it comes to trading future picks. He can still trade all or part of the Blazers' 2024 pick that doesn't fall outside the protections. The Blazers keep that pick if it falls in the lottery again, and they have the ability to trade it to another team with wording that it only conveys if it falls 1-14, or a smaller window of protection like, say, 4-14. In the latter scenario, they'd keep the pick if it landed in the top three, send it to the other team if it lands outside the top three but still in the lottery, and to Chicago if it's not in the lottery. It gives them another asset to move, but it's incredibly risky—if the Blazers missed the playoffs again next season, there's a chance they'd have no pick to show for it.
The other thing they can do is trade unspecified future first-rounders tied to the Bulls pick conveying. When pick protections are tied up years out in the future, they can still trade future first-rounders and swaps if they're worded as conveying in the "first allowable draft." That could be up to two first-rounders and three swaps if they make the trade before July 1, or three firsts and three swaps after that, when they gain access to their 2030 pick.
Let's say they were to do this, and then made the playoffs next season and gave their 2024 pick to Chicago. In that case, the "first allowable draft" under the Stepien rule would be 2026, and the team they traded the future picks to could receive their first-rounders in 2026, 2028 and 2030, as well as swaps in 2025, 2027 and 2029. If the pick didn't convey to Chicago in 2024, all of that would be delayed until it does.
As you might imagine, these kinds of negotiations can get complicated, and teams may be less interested in the sorts of trades Portland is going after if they don't know exactly what years they're getting the picks. It will be easier for everybody if the Blazers are able to figure something out with the Bulls and regain some of that certainty.
Pulling off the kind of trade Cronin is looking for is tough to begin with. Straightening out their draft-pick situation is just another obstacle to navigate.