What if Kirk Dillard had found another 194 votes?
Dillard was a staffer to both Jim Thompson and Jim Edgar, and he would have fit right into that line of Illinois governors that ended with George Ryan: moderate, gray-haired, Republican, boring. Quinn would never even have been in the race against Dillard, who holds none of Bill Brady’s prehistoric social views. Dillard would have served for eight years, without anyone noticing we’d changed governors since the 1980s.
What if Rickey Hendon had not run for lieutenant governor?
Hendon didn’t actually want to be lieutenant governor. He just wanted to prevent his West Side rival, Art Turner, from becoming lieutenant governor. And he succeeded, by splitting the black vote in Chicago. If Hendon’t hadn’t run, then Turner, the party’s chosen candidate, would have defeated Scott Lee Cohen, sparing the Democratic Party a lot of embarrassment.
What if David Hoffman had won the Democratic nomination for U.S. Senate?
After Alexi Giannoulias won the February primary, there was a lot of talk that the Democrats had nominated the wrong man, and that if the election had been held in March, Hoffman would have won. Maybe, but I don’t think Hoffman would be doing any better against Kirk. He was not a particularly strong candidate. In debates, he came off as a know-it-all and a tattle tale, kind of like Kirk. His base was among white liberal voters. The last white Chicago Democrat to win a U.S. Senate election was Paul Douglas, in 1960.
What if Lisa Madigan had run for the U.S. Senate?
Madigan could have broken that string of defeats for white Chicago Democrats. She is extremely popular among suburban women, the folks who decide elections in Illinois. But slow-moving Washington would have felt like exile to Madigan, who was raised on exciting Chicago politics, and really wants to be governor. Madigan could have been the senator, but she wouldn’t have been a good one. It’s not where her heart is.
What if Mayor Daley had not announced his retirement in September?
The biggest casualty of Daley’s surprise announcement may be Forrest Claypool, who was fighting to get attention for his independent run for the obscure office of Cook County Assessor. Claypool had the entire Chicago news media in his corner, but they were suddenly distracted by the race for the less obscure office of mayor. As Nadig Newspapers political columnist Russ Stewart put it, in predicting a victory for Joe Berrios: "Mayor Rich Daley's retirement sucked the oxygen out of independent Forrest Claypool's campaign. Claypool has failed to ignite voters or to construct a viable coalition of anti-Obama conservatives and pro-Obama (but anti-Machine) liberals.”