4. DeMar DeRozan
For much of the second half of the 2010s, the Bulls had been searching for their next franchise star. A guy that was a legitimate All-NBA candidate and whose abilities would be able to propel the franchise back to its former glory. Someone that would be able to restore honor to Chicago basketball. No, not a Michael Jordan-level player, but just someone that could give the franchise legitimate relevancy.
In the summer of 2021, it looked like the Bulls might have found their guy. When the front office pulled off a sign-and-trade for DeMar DeRozan with the San Antonio Spurs, the scoring machine that made a name for himself with the Raptors was on his way to Chicago, and things were finally beginning to look up in the Windy City.
As we expected, DeMar completed an excellent first season with the Bulls in 2021-22. He was named to the All-NBA second team, and finished in the top ten for MVP voting while being nominated an All-Star as well. But as Chicago fell down in the standings toward the end of the year due to injuries, the DeRozan experience started to fade a bit.
His two seasons since then have still been solid from an individual perspective, but it is clear the Bulls will not be making any kind of legitimate playoff run with DeMar at the helm. He will be an unrestricted free agent this summer, and it seems like a near certainty that he moves on.