Sam Quinn of CBS Sports ranked the value of all 63 first-round draft picks that have been traded in the NBA. Coming in at No. 36 is the first-round pick that the Portland Trail Blazers still owe the Chicago Bulls as a result of the head-scratching Larry Nance Jr. trade.

That pick is lottery-protected, which, on the surface, makes it surprising that it’s deemed so valuable. However, the dilemma lies in Portland trying to maximize its return from the blockbuster Damian Lillard trade.

Portland has Milwaukee’s first-round pick in 2029 and first-round pick swaps in 2028 and 2030. Meanwhile, the pick they owe the Bulls will become a second-round pick if it isn’t conveyed by 2028.

In other words, if Portland misses the playoffs in 2026 and 2027, but returns in 2028, that first-rounder would still go to Chicago. That’s a realistic possibility given the strength of the Western Conference and the trajectory an ascending 36-win Blazers team is heading in. That would also be a nightmare scenario for Portland — they wouldn’t be able to use Milwaukee’s pick swap that year, because they wouldn’t have a pick to swap.

Portland wants to avoid this scenario by any means necessary, which gives Chicago unique leverage despite it being a lottery-protected pick.

Blazers must proactively avoid nightmare scenario in 2028

“There is no way Portland is going to risk losing those Milwaukee swap rights. Therefore, the Bulls can hold this pick hostage and sell it back to Portland for a premium,” Quinn writes. “The longer the Blazers take to trade for it back, the more valuable it becomes to them. Portland should be trying to get this pick back here and now, while the price is still likely reasonable. If they have to wait until 2028, Chicago is going to command a far steeper price to give it back. So in a vacuum, this Portland pick won’t be great. As a bigger picture asset, though, it has a chance to prove pretty meaningful.”

Quinn also notes that he doesn’t expect Giannis Antetokounmpo to be in a Bucks jersey by 2028. The Blazers front office is hoping that’s the case, as Milwaukee has a flawed roster outside of Giannis and will have a difficult time making upgrades with Lillard’s $113 million in dead money limiting their flexibility over the next five years.

With Giannis potentially gone by then, Portland could be swapping into a top ten selection. Quinn ranks the 2028 pick swap as the 15th most valuable traded first-round pick. Of course, the Blazers need to make sure they can actually make the swap.

Ideally, the Blazers make the postseason in the next two years, and this all goes away. But the additions of veterans Jrue Holiday and Damian Lillard, combined with their young core’s inevitable growing pains, put Portland on track to return to the postseason right around 2028.

As Quinn notes, the Blazers need to be proactive and work something out with the Bulls sooner rather than later. The longer they wait, the more valuable that protected pick they owe Chicago will become.