[2] After graduating from Georgetown in 2003, Flannery would earn his Juris Doctor from Northern Kentucky University's Salmon P. Chase College of Law in 2008.

[2] After returning home, Flannery opened his own private law practice and was elected Carter County Attorney in 2010.

[3] He has also served in various roles involving tax law including executive director of the Kentucky Board of Tax Appeals and deputy director of the Kentucky Claims Commission under the leadership of Governor Matthew G. Bevin and Secretary David Dickerson.

[6] During the 2023 Kentucky General Assembly, Flannery was the primary sponsor of HB 170, which required health insurance companies to cover reproductive preservation in cases of testicular or other urological cancers.

[7][6] Flannery has also promised to introduce a resolution every year recognizing April as Testicular Cancer Awareness Month, which he did in both the 2023[8] and 2024 Kentucky General Assemblies.