[6] Two years later, however, he decided to seek elected office again, running for United States House of Representatives, challenging then-eight term incumbent Republican congressman Lawrence H. Smith in Wisconsin's 1st congressional district.

He defeated perennial candidate Kenosha engineer Erling Johnson in the Democratic primary, but lost to Smith in the general election.

[2][7][8] Congressman Lawrence Smith died a year into his ninth term, in January 1958, and Flynn decided to run again for the first congressional district, which would then be an open seat in the 1958 election.

[9] He faced another competitive primary—this time against fellow attorney Sverre Roang, of Edgerton, Wisconsin—but managed to prevail with strong support from Racine and Kenosha counties.

Schadeberg was considered a political unknown, but was popular from years of church and civic engagement, and was assisted by the district's natural Republican majority.

[16] Flynn did not run for office again after coming in a distant third in the 1970 Democratic primary behind Les Aspin and Doug La Follette.

He collapsed in the courtroom of Wisconsin circuit judge Emmanuel J. Vuvunas during a trial and died at Racine's St. Luke's Hospital later that day.

[2] In addition to his legal and political career, Flynn was active in the Catholic community as a member of the Society of the Holy Name and the Knights of Columbus.