Kengor has worked with conservative think tanks like the Center for Strategic and International Studies, The Heritage Foundation, and the Allegheny Institute for Public Policy. He serves on the editorial board of Presidential Studies Quarterly and provides regular commentary for American Radio Journal, Moody Broadcasting, and Ave Maria Radio Network/CatholicExchange.com. He also writes for The American Spectator and was named editor of the magazine in 2022, succeeding founder R. Emmett Tyrrell, Jr., though Tyrrell remains editor in chief. Kengor has published eight books on Ronald Reagan, including The Crusader: Ronald Reagan and the Fall of Communism, which inspired the 2024 film Reagan, starring Dennis Quaid.