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Selected as a Kentucky Super Lawyers® Rising Star for 2018 and 2019 in the area of Tax Law, Bailey represents taxpayers in federal, state, and local tax controversies as a member of the Firm’s Tax & Employee Benefits practice group. Bailey regularly advocates for clients in the state courts and administrative tribunals of Kentucky, Ohio, and Indiana, as well as the United States Tax Court. Her expertise encompasses income tax, sales tax, property tax, trust and estate tax, and excise tax, and she advises clients in the manufacturing, retail, tobacco, and alcohol industries, as well as many others. She also assists clients with their tax planning and compliance needs.

Bailey has broad experience dealing with the Internal Revenue Service and state and local tax departments to settle disputes on behalf of taxpayers. She has successfully negotiated with the Internal Revenue Service and state tax departments to resolve tax collection issues through offers in compromise, installment agreements, and removal of liens and levies.

Bailey also serves as General Counsel for the Kentucky Democratic Party. She formerly served as President of the Board of Louisville Girls Leadership, is a 2016 graduate of Leadership Louisville’s Ignite Louisville Program, and is a 2015 graduate of Emerge Kentucky.

Bailey is a graduate of William & Mary Law School and Boston University.

Career Highlights

Representative Cases and Achievements

Bailey has successfully provided counsel to and advocated for taxpayers in numerous federal, state, and local tax controversy and planning matters, both in administrative tribunals and the courts. She has represented many types of taxpayers, including corporations, limited liability companies, and individuals, and she has handled cases involving potential tax liability ranging from several thousand to several million dollars. Bailey has negotiated resolutions to tax collection disputes with the Internal Revenue Service and numerous state tax departments and has assisted clients in obtaining offers in compromise, installment agreements, and removal of liens and levies from their property.

Bailey is currently involved in or has been involved in the following cases:

  • Ashland Specialty Co., Inc. v. Matkovich, Civil Action No. 14-AA-102 (W. Va. Cir. Ct. 2017), on appeal, No. 17-0437 (W. Va. 2017) (pending) (abuse of discretion and excessive fines dispute involving a tax penalty)
  • The Auto Place, LLC, et al. v. Testa, Case Nos. 2015-474, 2015-475, 2015-479 (Ohio Bd. Tax. App. 2015) (pending) (sales and consumer use tax dispute involving purchases and sales of high-value classic cars)
  • Humana Inc. v. Dep’t of Revenue, File No. K16-R-03, Order No. K-25212 (Ky. Claims Comm’n Feb. 2, 2017), on appeal, No. 2017-CI-001265 (Ky. Cir. Ct. 2017) (pending) (sales and use tax dispute involving manufacturing)
  • Kroger Limited Partnership I v. Scott County Property Valuation Admin., et al. File No. K16-S-07, Order No. K-25128 (Ky. Bd. Tax App. Jul. 12, 2016), on appeal, No. 16-CI-00435 (Ky. Cir. Ct. 2016) (pending) (property tax dispute involving big box grocery store)
  • Lafarge North America, Inc. v. Testa, Case No. 2015-763 (Ohio Bd. Tax App. Jun. 21, 2016), on appeal, Case No. 2016-1074 (Ohio 2017) (pending) (sales and consumer use tax dispute involving manufacturing)
  • T. Ryan Legg Irrevocable Trust v. Testa, 2016-Ohio-8418, 2016 WL 7449356 (Ohio 2016), petition for cert. denied, (U.S. 2017) (No. 17-84) (due process challenge)
  • OVWD, Inc. v. Commonwealth, et al., No. 2015-CA-000754-MR (Ky. Ct. App. Mar. 24, 2017), on appeal, 2017-SC-000194 (Ky. 2017) (pending) (motion for discretionary review to Kentucky Supreme Court involving Section 2 of the Kentucky Constitution and exhaustion of administrative remedies)
  • OVWD, Inc. v. Commonwealth, et al., File No. 13-R-15, (Ky. Bd. Tax App.) (pending) (cigarette tax dispute involving out-of-state sales)
  • LaRue County Geriatric Center, Inc. c/o Signature Healthcare v. LaRue County Property Valuation Admin. et al., File No. K16-S-76 (Ky. Claims Comm’n) (pending) (property tax dispute involving not-for-profit nursing home)
  • T-Mobile South, LLC v. Kentucky Commercial Radio Service Emergency Telecommunications Board, Nos. 09-CI-1436; 15-CI-1124 (Ky. Cir. Ct.) (pending) (CMRS fee common law refund claim for prepaid wireless charges)
  • Wal-Mart Stores East, LP, et al. v. Dep’t of Revenue, No. 2016-SC-000550 (Ky. Mar. 15, 2017) (refund claim involving Section 51 and Section 180 of the Kentucky Constitution)


  • Recognized as a "Kentucky Rising Star" in the Kentucky Super Lawyers® list, 2018-2019
  • M&A Today Global Award in the category of Kentucky Corporate Tax Law Firm of the Year, 2016
  • Continuing Legal Education Award, Kentucky Bar Association, 2016
  • Boston University Scarlet Key Society
  • William & Mary School of Law Dean’s Certificate
  • William & Mary School of Law Public Service Award


Professional Affiliations

  • Kentucky Bar Association
  • Louisville Bar Association
  • Council on State Taxation
  • Institute for Professionals in Taxation

Community Involvement

Professional Leadership

  • Member, Finance and Administration Cabinet Transition Team for Governor-Elect Andy Beshear, 2019
  • Chair, Louisville Bar Association Taxation Section, 2016
  • Vice Chair, Louisville Bar Association Taxation Section, 2015

Civic and Charitable Involvement

  • General Counsel, Kentucky Democratic Party, 2018
  • President of the Board, Louisville Girls Leadership, 2016-2018
  • Treasurer of the Board, Louisville Girls Leadership, 2015-2016
  • Ignite Louisville, Class of Fall 2016
  • Emerge Kentucky, Class of 2015
  • Member, Junior League of Louisville, 2014-2015
  • Focus Louisville, 2014
  • Habitat for Humanity Global Village Project, 2012


Contributions & Published Works

  • "Delaware Trust Seeks Review of Ohio Supreme Court Opinion," State Tax Notes, co-author, Vol. 85, Num. 11, 2017
  • “Defamation, Humiliation, and Lost Reputations: Mitigating the Damage to Women Harassed Online,” Women’s Rights Law Reporter, 35 Women’s Rts. L. Rep. 123, 2014

Tax Law Insights


  • Ethics for Property Tax Lawyers and Consultants, ABA/IPT Property Tax Seminar – New Orleans, March 23, 2018
  • National Update – Discussion of State Tax Cases, Issues and Trends to Watch, COST Regional Meeting – Cincinnati, June 15, 2015
  • “Understanding Sales and Use Tax,” NBI Business Law Boot Camp, June 29, 2017
  • "Impact of Environmental Issues on Property Tax Assessments: Potential Tax Reduction Opportunities that May Offset Environmental Compliance Costs," 15th Annual Kentucky Environmental Conference, March 28, 2017
  • "What State’s My Trust In? Can I Move It? Income Tax Situs of Trusts and Related Issues," Indianapolis Bar Association, 2015


  • Boston University, B.A., magna cum laude, Political Science, 2010
  • William & Mary School of Law, J.D., 2013
  • Boston University, M.A., magna cum laude, Political Science, 2010
  • Council on State Taxation State and Local Tax Basics School, 2015
  • Institute for Professionals in Taxation Sales Tax School I, 2016
  • Kentucky, 2013
  • Indiana, 2014
  • U.S. District Court for the Western District of Kentucky, 2014
  • U.S. Tax Court, 2016
  • U.S. Supreme Court, 2017
  • U.S. Court of Appeals for the Sixth Circuit, 2018
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