The Chicago Bulls are fortunate enough to head into the 2026-2027 NBA season with low pressure.
Being in a rebuild with a new coaching staff and a revamped front office, now is the time for the Bulls to experiment.
Making trades to acquire young prospects to build a stronger future is a priority for Chicago. Recently, the Bulls were urged to consider calling up the Portland Trail Blazers for a former top-three pick in Scoot Henderson.
What kind of offer could the Bulls make to possibly intrigue the Blazers?
Bulls Trade Proposal Brings Former Top-3 Pick to Chicago
GettyPHOENIX, ARIZONA – APRIL 14: Scoot Henderson #00 of the Portland Trail Blazers handles the ball against Jalen Green #4 of the Phoenix Suns during the second half of an NBA play-in tournament game at Mortgage Matchup Center on April 14, 2026 in Phoenix, Arizona. The Portland Trail Blazers defeated the Suns 114-110. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Christian Petersen/Getty Images)
The idea: In this hypothetical, the Bulls would receive the fourth-year veteran Scoot Henderson.
The Blazers would pick up the guards Tre Jones and Isaac Okoro, along with a 2027 second-round pick from the Cleveland Cavaliers, and a 2029 second-round pick from Chicago. A two-for-one, along with future compensation.
Why Should Chicago Consider This Deal?
GettyPORTLAND, OREGON – MARCH 25: Scoot Henderson #00 of the Portland Trail Blazers and Ryan Rollins #13 of the Milwaukee Bucks greet each other after the game at Moda Center on March 25, 2026 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Soobum Im/Getty Images)
This would be a buy-low opportunity for a guard who was a top-three prospect entering the NBA Draft. After Victor Wembanyama and Brandon Miller went off the board, the Blazers picked up Henderson. He’s just 22, and certainly fits Chicago’s timeline.
The familiarity between first-year Bulls head coach Tiago Splitter and Henderson helps as well. Splitter was Henderson’s head coach last season.
Through three NBA seasons, Henderson has appeared in 158 games. He shoots 40.4% from the field and 34.4% from deep, producing 13.5 points per game.
The Bulls would get Henderson on an expiring deal. If he struggles, they can try to flip him in a sign-and-trade, or allow a team to outbid for him in restricted free agency. Okoro helps the Bulls land value for his expiring deal. Tre Jones might leave them hesitant, but he has been deemed a potential mover this offseason.
What’s The Benefit For The Blazers?
GettySALT LAKE CITY, UTAH – FEBRUARY 12: Scoot Henderson #00 of the Portland Trail Blazers drives past Oscar Tshiebwe #34 of the Utah Jazz during the first half of a game at Delta Center on February 12, 2026 in Salt Lake City, Utah. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Alex Goodlett/Getty Images)
Now that Portland plans to compete for a playoff spot in the Western Conference, Okoro and Jones offer win-now depth.
Henderson is in a tricky spot, since the Blazers have notable names featured in the backcourt for next year. Damian Lillard is set to return. Ja Morant is arriving. Jrue Holiday isn’t going anywhere.
Henderson might not be ready to beat out those guys for minutes, as the Blazers look to make another playoff bid. The Bulls could give them some additional picks, along with players they won’t have to worry about being tied to long-term.
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