2. The Bulls shouldn’t have let Pascal Siakam slip by in the 2016 Draft
Sticking to their mantra of shooting over everything, the Bulls selected a relatively unskilled player in Denzel Valentine at No. 14 in the 2016 NBA Draft. Once again ignoring international talent, Pascal Siakam would emerge as arguably the best player of his draft class at the 27th spot. With two All-NBA nominations under his name already, Siakam would certainly have been the best player in a Bulls uniform since 2016.
Dejounte Murray (29th) and eventual Rookie of the Year Malcolm Brogdon (36th) were also still on the board, each of whom would have put an end to Chicago’s long-standing point guard vacancy. To this day, this team is still trying to pick up the pieces from the error made on that draft day.
3. Chicago butchers the Butler trade and misses out on a great 2017 Draft class
Sending Jimmy Butler to the Timberwolves, the Bulls actually gave up the No. 16 pick in that deal and only received one pick (No. 7) in return. In today’s market, a player like Butler would fetch at least four first-rounders and likely a few swaps, but the Bulls effectively only received one swap. This was used to select Lauri Markkanen, a player who would immediately become an All-Star after the Bulls failed to develop his game and sent him packing.
If Chicago had kept both the 7th and 16th picks — and possibly more, if they were competent negotiators — they would have had the opportunity to select massive difference-makers such as Donovan Mitchell, Bam Adebayo, OG Anunoby, or Kyle Kuzma.