In 1978, incumbent Democrat John Dent of Pennsylvania's 21st congressional district decided to retire. Bailey ran and won the Democratic primary with a plurality of 23% in an 11 candidate field. He won the general election with 53% of the vote. In 1980, he was challenged by two candidates in the primary, but he defeated both of them in April with 60% of the vote. He won re-election to a second term with 68% of the vote. After redistricting by the state legislature, Bailey's district in 1982 was one of two eliminated as a result of slow-growth in Pennsylvania compared to other states. Most of his district, including his home in Westmoreland County, was merged with the 12th District of fellow Democratic Congressman John Murtha, who had been serving since 1974. Despite the fact that most of the district was represented by Murtha, Bailey decided to run in the newly redrawn Pennsylvania's 12th congressional district. Murtha defeated Bailey in the primary 52%–38%.
Tenure
He was generally considered as a moderate-to-conservative Democrat. In 1979, he sponsored legislation to fund synthetic fuel. He frequently criticized Democratic President Jimmy Carter. However, when Carter was challenged by liberal U.S. Senator Ted Kennedy, Bailey and most Western Pennsylvania Democrats endorsed Carter. Bailey said "Carter is still the best alternative." He negotiated for loans for the Wheeling-Pittsburgh Steel company. In 1981, he opposed raising the retirement age. He also voted against spending cuts proposed by Republican President Ronald Reagan and against a Balanced budget amendment.
In 1984, Bailey ran for Pennsylvania Auditor General as a Democrat, defeating Republican Susan Shanaman 51%–48%. He was the only Democratic nominee to win statewide that year. During his tenure as Auditor General, Bailey established the first work-site child daycare facility in Pennsylvania government, established minimum education standards for state auditors, and generally modernized auditing procedures.
Legal career (1989–2013)
Since leaving the Auditor General office in 1989, Bailey became a full-time attorney, based in Harrisburg, Pennsylvania. His specialties include civil rights. He is also quoted as calling himself, an "equal opportunity suer " and does take clients litigating with both Democrats and Republicans. On October 2, 2013, the Supreme Court of Pennsylvania suspended Bailey from practice for 5 years
Bailey decided to challenge incumbent Republican U.S. Senator Arlen Specter. However, he lost the Democratic primary to U.S. Congressman Bob Edgar 47%–45%.
Bailey ran for Auditor General again in 1992. He lost the Democratic primary to State Senator H. Craig Lewis, who won with a plurality of 40% of the vote. Businessman Jack O'Brien ranked second with 27%, Bailey ranked third with 20%, and State Senator Roy C. Afflerbach was last with 12%.
1998 gubernatorial election
In 1998, Bailey ran for Governor of Pennsylvania, challenging incumbent Republican Governor Tom Ridge. Bailey lost the Democratic primary to State Representative Ivan Itkin 49%–39%.