He knows why and I'll take it a step further and say it's not his fault directly.
the media from print media to tv to now the internet has created and and continues to cyse this view of the Black Man as a threat to them. It's been that way for centuries. You consistently see and read this agenda of the black man as a violent and dangerous creature going back from early literature to the media of today. It's beaten in your head that a certain "look" presented on a black man is one thing even though it's COMPLETELY different with whites.
Just an example:
pack of black kids walking down the street - gang (about to rob you/beat you up threatening)
pack of white kids doing the same - friends having fun (non threatening)
We've been "taught" by the media that black me doing, saying, or wearing certain things are "dangerous". In that respect, I see where Cuban's prejudice comes from.
Everyone wants to be judged as an individual and not grouped into one bucket, but when you are fighting a systematic label already attached to you as a black american, you are fighting an uphill battle from the womb.
The media and those who control it KNOW that this type of fear mongering and rhetoric sells, gets them ratings, etc. Look at the shift in hip hop once major corporations took over. There was balance back from the early 80s to early/mid 90s. That shyt is gone now and replaced with the same guns, sex, and violence that they know generate ratings. The people who put this shyt out and more importantly control it don't have to worry about the messages portrayed and how destructive it can be to their community since they don't have to deal with the shyt in their privileged communities.
Back on topic, Cuban knows why he brought up the hoodie example and should just be COMPLETELY honest in the fact that "image" of a black man in said hoodie is a threating image instilled in his beliefs in general so he fears that individual. The roots of the fear and prejudice are the deeper issue IMO.
The only one I've found in life to confront racism and bigotry is to actuallly spend time with people of varying ethnicity, class, and beliefs. And most important, be honest.