In 2001, Conway launched a challenge to then-Rep. Ann Northup (R-Ky.) in Kentucky's 3rd district, a swing seatthat had only voted for Al Gore by 2 points in the 2000 presidential race. The race soon became a key House battleground. Yet, what was long one of Democrats' most promising pick-up opportunities shiftedi n Northup's favor. Conservative groups vastly outspent Conway; Patton became embroiled in a late-breaking scandal.; and the cycle proved more favorable to Republcans nationally than had been expected. Even so, Conway lost by 3 points, or a margin of less than 8,000 votes.

After his defeat, Conway worked as a trial attorney. In 2005, Democratic Congressional Campaign Committee Chairman Rahm Emanuel tried to convince Conway to seek a rematch against Northup, but he declined.

Attorney General

In 2007, Conway mounted a second attempt at elected office and ran for attorney general. He faced state Sen. Stan Lee (R), whom he lambasted as an extremist. "This is not an office for zealotry," he said. Lee returned the favor by attacking his opponent as an "ultra-liberal" and a "big city trial attorney," but the message did not stick.

Conway triumphed with 61 percent of the vote.

2010 Senate race

In 2010, Conway decided to challenge Sen. Jim Bunning (R-Ky.). A few months into his campaign, Bunning announced he would not seek reelection, transforming the contest into an open race.

Conway first faced a competitive primary against LG Dan Mongiardo (D). The race quickly turned negative, with Mongiardo using Conway's Louisville origins to portray him as the candidate of the urban elites; he even distributed plastic silver spoons to his followers to claim his opponent stood for "silver spoon issues preferred by the champagne and caviar crowd."

While Mongiardo long led in polls, Conway closed the gap thanks to his fundraising advantage, his ability to donate to his own campaign and the support of much of the state's Democratic establishment.In the campaign's final stretch, Conway emphasized his support for reforming the health-care system, blasting Mongiardo for opposing it. On Election Day, Conway prevailed by less than 1 percentage point thanks to his dominance in the Louisville region.

Conway then faced ophthalmologist Rand Paul (R), son of Rep. Ron Paul (R-Texas) who beat the early Republican frontrunner to earn a spot in the general election. With the national media swarming to Kentucky to cover Paul's unconventionally libertarian politics, Conway attacked his opponent's "risky and radical" ideas.

But Conway struggled in the face of his party's declining fortunes nationally, with Paul tying him to "his liberal Washington, D.C., buddies." Both candidates have also battled over who is the best advocate for the coal industry.

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