In 2000, Schiff challenged Republican incumbent Jim Rogan in what was then the 27th district. The district had once been a Republican stronghold, but had been trending Democratic since the early 1990s. In what was the most expensive House race ever at the time (several elections in 2006 and 2008 later eclipsed it), Schiff unseated Rogan, taking 53 percent of the vote to Rogan's 44 percent. He became only the second Democrat to represent this district since its creation in 1913.