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Rob Dillingham poised to flip Bulls' trade deadline narrative

The 21-year-old has something no other Chicago guard has.
Andrew Hanlon
Andrew Hanlon

Pippen Ain't Easy

Feb 9, 2026; Brooklyn, New York, USA; Chicago Bulls guard Rob Dillingham (7) goes to the basket against Brooklyn Nets forward Danny Wolf (2) during the first half at Barclays Center. Mandatory Credit: Vincent Carchietta-Imagn Images / Vincent Carchietta-Imagn Images

The Chicago Bulls reshaped their roster at this year's trade deadline, but one player could tip the scales between success and failure: Rob Dillingham.

Chicago's unusually active deadline was more about outgoings than incomings: Ayo Dosunmu landed in Minnesota as part of the deal that brought Dillingham to the Windy City. Coby White was traded to the Charlotte Hornets. Nikola Vucevic is now a member of the Boston Celtics.

The Bulls acquired Dillingham as the centerpiece of that Dosunmu trade. Taking a flier on a 21-year-old, former top-10 pick like Dillingham was clever on the part of executive VP of basketball operations Arturas Karnisovas.

Chicago also secured a slew of second-round picks and an opportunity to gauge the value of several young guards, including Jaden Ivey, Anfernee Simons and Collin Sexton. But no asset the Bulls acquired has the upside Dillingham possesses.

Rob Dillingham poised to show Bulls he was a trade deadline steal

The Timberwolves sent a 2031 first-round pick and a 2030 top-1 protected pick swap to the San Antonio Spurs in exchange for the No. 8 pick in the 2024 draft, which they used to select Dillingham. Minnesota viewed him as the heir apparent to Mike Conley.

(Conley, coincidentally, came to Chicago along with Dillingham, was traded again, waived, and ended up back in Minnesota. The NBA, am I right?)

But the Dillingham experiment never worked for the Wolves, who needed a point guard ready to lead a title-contender. Dillingham wasn't that. Realistically, the entire situation was more a result of Minnesota's poor insight than a misvaluation of Dillingham's talent.

The intrigue surrounding the former Kentucky standout's game remains. He has an elite first step, is an excellent ball handler and can score from all three levels. He's slight -- listed at 6-foot-2 and 175 pounds -- and raw as a decision maker, but you don't have to squint hard to see Lou Williams or Jamal Crawford.

Chicago's trade deadline is being underrated

Dillingham's development may decide his ultimate grade, but Karnisovas deserves a bit more praise than he's getting. (A bit.)

He grabbed another distressed asset in Ivey, who was becoming one of the league's most attractive young guards before he broke his leg and couldn't regain his footing in Detroit.

Second-round picks are more valuable in today's NBA than they ever have been -- and the one Chicago landed in the Vucevic-Simons swap is a potential game-changer.

No one will call Karnisovas's deadline moves exceptional. But acquiring Dillingham was a shrewd piece of business that's poised to make him look, well, not like a genius ... but a person who can be smart sometimes.

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.