I think McCain should have run against the Illinois Democrat machine as I'm sure Guiliani would have. The fact that Obama was made a Senator by Emil Jones who now gets a fat retirement package as part of the legitimized graft in that system is worth exploring. Obama decided to endores Mayor Daley's run for re-election when Obama had decided to run for president. A Washington Post article in Feb. 2007 offers more detail.
'Once he got to the state Senate, Obama was no radical. He became a
political protege of current Senate President Emil Jones, a 35-year
veteran of the legislature and one of the state's most influential
black lawmakers. ...Obama has lined up with party leaders in some recent
local races. He supported the party's choice to become the new Cook
County board president, despite allegations of political nepotism
surrounding the man, who was the son of the previous board president...Obama
also endorsed Daley, saying he was still concerned about City Hall
corruption but thought Daley had taken steps to clean it up. And he
supported the November re-election of Democratic Gov. Rod Blagojevich,
whose administration is under federal investigation for hiring fraud.'