Career
Born in Cornwall, O'Shaughnessy previously served as reeve of the nearby township of Charlottenburg in the 1990s, and ran as a Progressive Conservative Party of Canada candidate for Stormont—Dundas in the 1997 federal election. He later moved back to Cornwall, and was elected to Cornwall City Council in 2003. He ran for mayor in the 2006 municipal election, but was not elected.
He ran again in the 2010 municipal election and was reelected as a councillor, but resigned his seat in 2012 citing concerns about the council's commitment to accountability and transparency. In the 2014 election, he defeated incumbent mayor Bob Kilger.