In 1996, Blagojevich did not seek reelection to the statehouse but instead ran for , based on the North Side. The district had long been represented by Dan Rostenkowski, who served as chairman of the House Ways and Means Committee. Rostenkowski lost reelection in 1994 to Republican Michael Patrick Flanagan after pleading guilty to mail fraud. However, Flanagan was a conservative Republican representing a heavily Democratic district and was regarded as a heavy underdog. Blagojevich soundly defeated Flanagan by a nearly 2-to-1 margin, with support from his father-in-law. He was elected two more times, taking 74% against a nominal Republican challenger in 1998 and having only a Libertarian opponent in 2000.