3. Bobby Portis
Drafted 22nd overall in 2015, Bobby Portis is without a doubt among the best non-lottery draft picks made by the Chicago Bulls this century. Just when he was hitting his stride, however, the Bulls dealt him away for the washed-up remains of Otto Porter Jr. — a mistake Chicago is still paying for, as they still owe Washington their 2023 second-round draft pick from that trade.
While Porter Jr. would go on to have little to no impact on the Bulls, Portis would immediately continue improving in Washington before inking a very team-friendly deal with Milwaukee in 2020. Portis has averaged 13.1 points and 8.4 rebounds per game in three seasons with the Bucks, serving as a genuine Sixth Man of the Year-caliber player behind Giannis Antetokounmpo.
Most importantly, he played a pivotal role in Milwaukee’s 2021 championship run, something he’s he’s been keen to remind Bulls fans about.
Bobby Portis has a message for Bulls fans pic.twitter.com/Eh9iYY0ALT
— IKE Bucks Podcast (@IKE_Bucks) April 24, 2022
The Chicago Bulls traded away a championship-caliber player in Bobby Portis.
Few players have embodied the toughness and culture of Chicago as well as Portis over the last several years. I mean, how many other players can punch their teammate in the face and be celebrated for it?
Portis has discussed how big of an impact playing in Chicago has had on his career, particularly in regard to his relationship with beloved former Bulls Joakim Noah and Taj Gibson.
"“I can call these guys right now, I call these guys if I need anything, if I need advice about anything, they are still right there. They are my big bros.”"
I see no reason why Portis couldn’t have become a beloved player on that level in his own right, had Chicago committed to him long-term. As much as it hurts to not have Portis on the Bulls for a longer amount of time, it’s concerning that he’s still just the third-biggest missed opportunity on this list.