Wenstrup practiced podiatric medicine in Cincinnati for more than 24 years, before being elected to Congress.
Military service
Wenstrup joined the United States Army Reserve in 1998, attaining the rank of colonel in March 2017. In 2005 and 2006, he served a tour in Iraq as a combat surgeon with the 344th Combat Support Hospital. He called his deployment "the worst thing that ever happened to me and the best thing I ever got to do." Wenstrup was awarded the Bronze Star Medal and Combat Action Badge. During his tour of duty in Iraq, Wenstrup's sister asked what she could send him. He told her "I wear the same clothes everyday, we're fed, and most days I'm not leaving the base. But the people here have nothing. They were under an oppressed regime and have had nothing for so long." His sister helped organize donations of toys, school supplies, and hygiene supplies donated by local companies, and Wenstrup worked with the base chaplain to distribute the donations to the locals.
2009 Cincinnati mayoral election
Wenstrup ran for mayor of Cincinnati against incumbent Democrat Mark Mallory in the November 2009 election. Mallory defeated Wenstrup by a 54%-to-46% margin.
Wenstrup ran for the U.S. House of Representatives in the newly redrawn Ohio's 2nd congressional district, held by incumbent Republican U.S. Congresswoman Jean Schmidt. He was endorsed by the Anderson Tea Party and the Ohio Liberty Council, a coalition of Ohio Tea Party groups. In a surprise, he defeated Schmidt in the March Republican primary by 49%-to-43%. She carried six counties, while Wenstrup won the two most populous counties : Hamilton County and Clermont County. Wenstrup defeated Democratic nominee William R. Smith, 59%–41%.
2014
Wenstrup won re-election to a second term by defeating Democratic nominee Marek Tyszkiewicz 66%–34%.
2016
Wenstrup won re-election to a third term, defeating Democratic candidates William Smith and Janet Everhard 65%–32.82%–2.17%.
2018
Wenstrup defeated Democratic candidate Jill Schiller, 58% to 41%, to win election to a fourth term.
Tenure
Wenstrup began his first term on January 3, 2013. During his first year in office he held an open town hall meeting in each of the 8 counties in his congressional district, the last of which was in Adams County on July 29, 2013. Wenstrup's customer service survey received accolades from Roll Call. In the survey, 75% of respondents said they were "satisfied" or "very satisfied" with their experience with Wenstrup's office. Wenstrup was an original co-sponsor of H.R. 3949, VA Prescription Data Accountability Act 2017, which became law during the 115th Congress, 1st Session. The bill helps protect veterans receiving prescription medicines and prevents misuse of such prescription medicines.