Roskam is no stranger to an expensive, closely watched race with national implications. Twelve years ago, he narrowly defeated now-U.S. Sen. Tammy Duckworth, bucking that year’s midterm trend of GOP losses as Democrats took back control of the U.S. House. Duckworth at the time had the backing of party heavyweights such as U.S. Sen. Dick Durbin and now-Mayor Rahm Emanuel, and her story of her Black Hawk helicopter being shot down in Iraq was fresh in voters’ minds.