His chances are extremely low. Dane County is fastest growing county in the state and it is getting more progressive each year. African Americans in Milwaukee have not turned out that well in recent elections but that should change with Obama on the top of the ticket. The Fox River Valley is trending towards the Democrats. Lastly, the 5-10% of Democrats that don't believe in recalls and won't be voting in next weeks election will be back in November. All of these factors should be able to cancel out the circle of ignorance and the Northwoods boondocks.
Actually, St. Croix county grew quite a bit faster. And is nicely Republican too.
Dane County of course can't outvote the entire state. See Prosser.