Who knew that when the Portland Trail Blazers wanted to add Larry Lance Jr. to the trade that sent Lauri Markkanen from the Bulls to the Cleveland Cavaliers, Chicago would end up with the most valuable piece of the deal? That could be the case for the lottery-protected first-round pick Portland still owes the Bulls.

Then-Blazers president of basketball operations Neil Olshey (who was as unpopular with Portland fans as Arturas Karnisovas currently is in Chicago) felt comfortable parting with that pick and forward Derrick Jones Jr. in return for a steady role player. Oops.

But the deal was a coup for the Bulls, and it could get even better.

Bulls can extract even more value from Blazers pick if things break right

The selection in question is lottery-protected through 2028, so from a surface level, Chicago would presumably prefer Portland to make the playoffs soon so the pick conveys. A second first-rounder next summer in what’s projected to be a stacked draft class would be a solid asset for the Bulls as they try to continue building a young and deep roster.

Not so fast, though, as Sam Quinn of CBS Sports points out in a piece ranking all 63 of the NBA’s currently traded first-round picks. The Trail Blazers have the option to swap first-rounders with the Milwaukee Bucks in 2028, Quinn explains, adding that he expects Giannis Antetokounmpo to be elsewhere by then.

Should Portland not make the playoffs in 2026 or 2027 but make it in 2028, its pick will head to Chicago, and the Blazers would lose their swap rights with the Bucks, he explains.

“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. … 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.”

This is another, more alluring angle for the Bulls to contemplate. If the Blazers become desperate to get the pick back, Chicago can drive up the price and turn one lottery-protected first into more.

Based on the acquisitions of Jrue Holiday and Damian Lillard, Portland seems to have eyes on making the playoffs sooner than 2028. Lillard won’t return to the floor until 2027, though, and the Western Conference is loaded with talent. Nothing’s guaranteed.

There are a lot of moving parts to this scenario, but if it were to play out like Quinn suggests, it would be a massive, unexpected boost for the Bulls.