by Democrats to elect Republicans" and Gilchrest had carried the district for nine terms, Democratic leaders believed the district had "a moderate character" and was ready to support Kratovil competitively. In addition to targeting by the Democratic Congressional Campaign Committee, Gilchrest staffers held "Republicans for Kratovil" events. Gilchrest hinted early on that he would endorse Kratovil, being quoted as saying, "Let's see, the Republican Party, or my eternal soul?" and "Party loyalty, or integrity?" On April 17, 2008, an article in Politico announced that long-time Wayne Gilchrest campaign manager Lynn Caliguri, spouse of Gilchrest chief of staff Tony Caliguri, had joined the Kratovil campaign. In early September 2008, Gilchrest officially endorsed Kratovil. District 2 The district comprises parts of Harford, Baltimore, and Anne Arundel Counties, as well as small portions of the City of Baltimore, and has been represented by Democrat Dutch Ruppersberger since 2003. Prior to serving in Congress, Ruppersberger was Baltimore County Executive from 1994 to 2002. Ruppersberger serves on the House Permanent Select Committee on Intelligence, the House Committee on Appropriations, and the Democratic Steering Committee. The Republican candidate is Richard Matthews, a 28-year-old computer systems engineer from Orchard Beach, who is also the Anne Arundel County, Maryland organizer for the Ron Paul 2008 Presidential campaign. Matthews is a moderate Republican with libertarian political views on civil liberties and economic freedom. He opposes the Iraq War, and generally supports freedom of choice in both personal and economic matters. District 3 The district comprises portions of Baltimore, Howard and Anne Arundel counties, as well as a significant part of the independent city of Baltimore, and has been represented by Democrat John Sarbanes since 2007. Sarbanes faced off against Republican candidate Thomas Harris; in this staunchly liberal district, Harris faced little chance against the popular Sarbanes. District 4 The district comprises portions of Prince George's and Montgomery Counties, and has been represented by Democrat Al Wynn since 1993. Coming off a close primary against progressive advocate Donna Edwards in 2006, Wynn faced a competitive primary against her again in 2008. While Wynn made an effort to appear more progressive, he remains one of the most conservative members of the Congressional Black Caucus. This time, Edwards defeated Wynn in the primary. Wynn then announced he would be leaving Congress before his term's expiration in January 2009, which triggered a special election. District 5 The district comprises all of Charles, St.