Kirk Dillard was supposed to be the Gov in 2010, he was respected by Dems and Rs and Indies, and Mark Kirk and Rauner were attached to him. Dillard wanted to raise revenue by putting a casino in Chicago, but Rauner never delivered on it. The Chicago transit system is the worst out of Denver, Dallas, LA and SF and NY. The casinos were needed to fund mass transit. Promises weren't fulfilled, that's why Rauner and Kirk were booted
Kirk Dillard endorsed Obama in 2008. Despite how popular he had been with the Illinois GOP, that sunk any chance he had. Its actually surprising he ran as well in the primary as he did considering that.
And what the heck are you talking about, Chicago has a better transit system than Denver, Dallas, LA and SF by any measure.