FEBRUARY 13, 2009: Mayor Richard M. Daley's administration seals a deal to lease Chicago's parking meter operation for 75 years in exchange for an upfront payment of $1 billion--an arrangement now famous as a boondoggle. We are still not sure how much the mayor profited from it, but it certainly was selling the city down the tubes and resulted in really, really expensive parking. A really, really unlucky day for Chicago.
JUNE 13, 2014: Donald Trump answers complaints from Mayor Rahm Emanuel and Tribune architecture critic Blair Kamin that the large new sign on Trump's building is tasteless. The Donald insists that "everybody loves it" because "we're probably the hottest brand there is."
Sorry, The Donald's Hair Is the Hottest Brand. --Cooter
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