He unsuccessfully ran again for his seat in 2024, losing the Republican primary to T. J. Roberts.
He earned a Bachelor of Science degree in criminal justice and police science from Eastern Kentucky University and a Juris Doctor from the Salmon P. Chase College of Law at Northern Kentucky University.
[2] Massey is licensed to practice law in Kentucky, Ohio, and Indiana.
He was also a board member of the National PTA, National Underground Railroad Freedom Center, New York Says Thank You Foundation, American Public Education Foundation, and Boone County Schools.
[3] Massey was elected to the Kentucky House of Representatives in November 2018 and assumed office on January 1, 2019.