Jrue Holiday is a two-time NBA champion and has designs on competing for a third with the Portland Trail Blazers, which is good news for the Chicago Bulls. If Holiday does indeed help lead Rip City to the playoffs, Chicago would add a valuable first-round pick to its stash in the 2026 NBA Draft.

Then-Blazers president of basketball operations Neil Olshey (who could’ve given current Bulls executive Arturas Karnisovas a run for his money as far as unpopular front office leaders go) jumped into the trade that sent Lauri Markkanen to the Cleveland Cavaliers in 2021. Olshey brought Larry Nance Jr. to Portland in exchange for Derrick Jones Jr. and a future first-round pick. That selection is lottery-protected through 2028.

If Holiday can help Scoot Henderson, Deni Avdija, Toumani Camara and the rest of his new teammates land a top-8 seed in the West, that pick will convey to Chicago in what’s projected to be a deep and talented draft class.

Jrue Holiday wants to help Portland hand the Bulls a first-round pick

Holiday has become a serial winner in the back half of his pro basketball career. He has two NBA titles on his resume, the first coming in 2021 with the Milwaukee Bucks and the second in 2024 with the Boston Celtics. He also played a crucial role in helping the United States win Olympic Gold Medals in 2020 and 2024.

The 35-year-old was part of a cost-cutting deal this summer when Boston sent him to Portland for Anfernee Simons and a pair of second-round picks. The Blazers haven’t made the playoffs since the 2020-21 season, but Holiday isn’t about to move from championships and Gold Medals to rebuilds, per Joe Freeman of The Oregonian/Oregon Live:

“I don’t really know how to do anything else. So come here and just be the person that I’ve always been … try to not just help out as much as possible, but to try to win. I think as a current player who’s won, (who’s) kind of been through the struggle not too long ago to win the championship, I still have that feeling and that itch. So I’m kind of closer to what that feeling is like and how hard it is to actually win.”

Trail Blazers guard Jrue Holiday

Portland is building a defense-first roster that suits Holiday perfectly. The Western Conference is deep, but the Blazers have a talented young core with Henderson, Shaedon Sharpe, Camara, Avdija, Donovan Clingan and the fast-rising Yang Hansen. In Chauncey Billups, they have a Hall-of-Fame coach who, as a player, led the 2004 Detroit Pistons — one of the best defensive teams of the last quarter century — to a title victory over Kobe Bryant, Shaquille O’Neal and the Los Angeles Lakers.

The Blazers have more than a puncher’s chance to make a playoff appearance this season. That means the Bulls have the same odds of landing an additional first-round pick next summer. That kind of asset can be invaluable to a team like Chicago, which is trying to build a young core that can make a playoff run of its own sooner rather than later.