Selected as a 2023 Best Lawyers “One to Watch,” in the area of Tax Law, and a Kentucky Super Lawyers Rising Star in Tax Law for 2018-2025, Bailey Roese has over a decade of experience representing and advising taxpayers in federal, state and local tax matters. As a member of Dentons Bingham Greenebaum’s Chambers USA Kentucky Band 1 ranked tax team, Bailey regularly advocates for clients in state courts, administrative tribunals, the United States Tax Court and US federal courts, including the US Supreme Court. Bailey also has broad experience working with the Internal Revenue Service, including IRS appeals, and state and local tax departments to settle disputes on behalf of taxpayers.
Bailey focuses much of her practice on captive insurance taxation, advising captives and their insureds on tax compliance and defending them during audit. Bailey appears at number 43 on the 2025 Captive Review “Power 50” list, and was included in Captive International’s 2025 “Forty Under 40” list. She received the “Captive Service Professional of the Year” award at the 2024 US Captive Awards. Bailey frequently speaks on captive insurance taxation, including at the Captive Insurance Companies Association (“CICA”) International Conference, the Vermont Captive Insurance Association (“VCIA”) Annual Conference, the World Captive Forum, and the Cayman Captive Forum, among many others. She is very committed to service to the captive industry. She is the current co-chair of CICA’s NEXTGen Committee and is an active member of its Amplify Women initiative. She serves on the Self Insurance Institute of America’s Captive Insurance committee. She has received her Associate in Captive Insurance designation from the International Center for Captive Insurance Education.