Wingard was appointed by Washington and Clackamas county commissioners to fill a vacancy in the Oregon House following the resignation of Jerry Krummel in August 2008, and announced his plans to seek election to a full term. During the campaign, it was revealed he was convicted in 2001 for misdemeanor assault for hitting his son on the head with a screwdriver. Wingard did community service and the conviction was eventually expunged. He won the November general election with 50% of the vote, defeating Democrat Jessica Adamson and Libertarian Marc Delphine. In 2010, Wingard won reelection with 61% of the vote, defeating Democrat Sandy Webb. During his two terms, Wingard's accomplishments include authoring HB2476 which toughens sentences against athletic coaches who sexually abuse their young athletes. The Bill was Signed into lawAugust 4, 2009. Wingard authored HB2512 which directs the Department of Transportation to issue Fallen Public Safety Officer registration plates. Wingard introduced House Bill 2754 to provide tax-credit scholarships to low- and middle-income children throughout Oregon. It failed to pass a key legislative deadline in mid-April. Wingard also co-sponsored HB3471 with Democrat Rep. Michael Dembrow to provide free college tuition to Oregon foster children. Wingard has been a longtime supporter of school choice and was the chief architect of the GOP education bills included in the Legislature's 2011 education reform package that passed over the objections of the state's teachers union. Wingard called the package, which included bills increasing access to online education and expanding their charter schools, "the most consequential legislation on education reform in Oregon history." After the reform bills passed, a Democratic lobbyist claimed Wingard had "outwitted his Democratic co-chair every step of the way." Wingard is a believer in "individual responsibility, limited government, constitutional democracy, property rights and the free market." In February 2010 Wingard ignited a minor controversy when he extensively quoted an article during a speech on the floor of the Oregon House. Some claimed it was plagiarism but Wingard says he simply didn't have time to cite his source.
Leadership Resignation
In early June 2012, Wingard resigned from his post as the Deputy Republican Leader of the Oregon House of Representatives following allegations that he pressured a young woman who worked in his office at the capitol into a sexual relationship. Then Republican House leaderKevin Cameron, told Wingard he would make a public call for his resignation if necessary. Wingard admitted to the Willamette Week that the two did have a sexual relationship, but denied using his position to pressure her and claimed that "a small group of socially conservative and well-connected Republicans, including one local party official, had been deeply involved in encouraging that staffer to make claims against me and had also spent the last two years digging around in my private life looking for more mud to sling." After Wingard abandoned his re-election campaign, his accuser recanted her most serious claims and he remained in office until the end of his term. His accuser went on to say "While he and I have an obvious disagreement about the nature of our relationship, I appreciate Mr. Wingard's tireless support for education reform in Oregon." Wingard's alleged wrongdoing, and his ensuing interactions with Cameron, became the subject of international press coverage amid speculation about a visit by several Republican lawmakers to a topless bar in California.
Personal
He has served on the Clackamas County Economic Development Commission and the Portfolio Options Committee of the Oregon Public Utility Commission.