I was involved in his first political outing, when he was running for the 9th (CD) back in the late 90's for Sydney Yates north suburban seat (won by Jan Shackowsky).
My God, he was seen as an absolute naive buffoon. The coalition around him was filled with political hustlers that took his money and laughed behind his back. It was pretty disgusting to see, and it was due to J.B. knowing nothing at all about politics besides that he had a lot of money and wanted to be in the game. The rough & tough streetwise old line Chi-town operators opportunistically saw him as a naive little rich boy, and took advantage of him without ever intending to deliver the goods. Consequently, his CD run was an abysmal failure.
I left that scene and the whole game immediately after and never gave J.B. a second thought, figuring he got used & abused and would simply disappear from the annals of political history.
Wow, was I wrong! Yeah, he learned, and eventually he succeeded. And he seems to be doing a great job. It's amazing the growth he's had over two decades, and the change in his personality. He always seemed like a decent guy from the first day I met him, but I never imagined he would ever develop the toughness, shrewdness, and political instincts required to prevail in Chicago politics. Good for him. Now, I kinda' wish I hung around!
