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Stephen A. Sherman

Counsel , Louisville KY


Stephen A. Sherman

Counsel , Louisville KY

Stephen serves as Counsel to the Firm in Stoll Keenon Ogden’s Louisville office and has been with SKO for more than 10 years. He contributes to the Tax practice and also the Business Services practice with a focus on Healthcare.

Tax: Working with clients ranging from individual persons to publicly traded companies, Stephen offers his expertise in matters concerning all areas of taxation, including corporate and personal income tax, wage assessments, excise tax, and property tax as well as tax exemptions, credits, and tax-related issues. Involved in all aspects of local, state, and federal taxation, Stephen has extensive experience in complex tax planning, audit defense, and tax controversies. He has represented clients before state revenue agencies, the IRS, and state and federal courts. He has significant expertise in tax-motivated transactions and the negotiation and implementation of tax incentives, including like-kind exchanges, corporate income tax credits, property tax abatements, the New Markets Tax Credit Program, and the Historic Rehabilitation Tax Credit.

Healthcare: Stephen represents providers from both nonprofit and for-profit organizations in various general business matters, such as employment matters, practice sales, mergers and acquisitions, and separations. He supports his clients in regulatory matters by applying for and challenging Kentucky Certificates of Need and other licensure requirements and assisting in Medicare and Medicaid audits and reimbursement disputes. He also advises on compliance with state and federal laws, including the Stark Law, Anti-Kickback Statute, and False Claims Act.

Business Services: Stephen’s proficiency in tax law, along with his knowledge of business concerns, including the unique challenges faced by healthcare systems, makes him a valuable asset to clients involved in business activities spanning from mergers and acquisitions to contract negotiations.


Holy Apostles College and Seminary, 2020, M.A. in Philosophy

University of Florida Fredric G. Levin College of Law, 2008, LL.M. in Taxation

Ave Maria School of Law, 2007, J.D.

University of Notre Dame, 2004, B.A.


Admitted In

  • U.S. Court of Federal Claims

  • U.S. District Court, Eastern District of Kentucky

  • U.S. District Court, Western District of Kentucky

  • U.S. Tax Court

  • Kentucky

Professional & Community Activities

  • American Bar Association

  • Louisville Bar Association

  • Kentucky Bar Association

  • Council on State Taxation

  • Kentucky Association of Economic Development

  • Louisville Bar Association, Leadership Academy, 2012

  • Louisville Bar Association, Taxation Section Chair, 2012, Vice-Chair, 2011

  • Kentucky Bar Association, Health Care Law Section, Secretary, 2018-2022, Chair-Elect 2022-Present

  • Community Catholic Center, Inc., Board Member, 2009 – 2012

  • St. Martin of Tours, Parish Council, 2018 – present

  • Angels in Disguise, Board Member and Secretary, 2022 – Present

  • Knights of Columbus

Work Highlights

  • Tax Planning

    Represented two major ophthalmology practices in the sale of their Kentucky and Indiana-based practices and associated ambulatory surgery centers to another business based in Missouri. The first $33 million transaction was structured as an asset purchase and the Second $30 million transition was structured as a stock purchase.

  • Sale of Kentucky and Indiana-based Ophthalmology Practices

    Represented two major ophthalmology practices in the sale of their Kentucky and Indiana-based practices and associated ambulatory surgery centers to another business based in Missouri. The first $33 million transaction was structured as an asset purchase and the second $30 million transition was structured as a stock purchase.

  • Reorganization, Refinancing, and Acquisition of Major Healthcare Entity

    Stoll Keenon Ogden represented a major healthcare services entity, its affiliated upstream and sister companies, its owners, and its founding management team in comprehensive reorganization, refinancing, and acquisition transactions totaling more than $300 million. The matters resulted in the closing of a senior secured term loan and revolving credit facilities secured by owned senior care facilities in four states with a 9-member syndicate of commercial banks; the requisition of waivers, consents and estoppels from various property lessors on leased senior care facilities in four states; restructuring of upstream holding companies and combination of two upstream ownership groups and boards of managers; the creation of a management company; the introduction of healthcare facility management agreements; the migration of payroll and benefits for more than 7,000 employees; the related restructuring of multiple lease and debt financing and supplier relationships; the creation and reorganization of multiple SPE organizations accompanied by extensive non-consolidation analysis and issuance of a substantive non-consolidation opinion to the lending syndicate; the exercise of purchase option and acquisition of multiple senior care facilities; the contribution of additional equity capital from the client’s majority owners; and the amendment and restructuring of multiple Master Lease and inter-creditor agreements.

  • Local Hotel Taxes

    Successfully defended online travel companies in litigation by three local governments seeking to collect local hotel taxes. Louisville/Jefferson County Metro Govt., Lexington-Fayette Urban County Govt., et al. v., L.P., et al., 590 F.3d 381 (6th Cir., 2009).


  • Utility Gross Receipts License Tax

    Successfully represented a provider of utility services in an appeal of a utility gross receipts license tax assessment that reduced their liability by $2.5 million.

  • Planning

    Advised client with respect to like-kind exchanges of multiple properties under Section 1031 of the Internal Revenue Code involving exchange proceeds in excess of $17 million.

  • Purchase of Gas/Food Marts

    Represented an oil company in the purchase of the assets and business of six gas and food mart locations.


    • Presentation to Kentucky Investors and Developers, Overview of Federal Opportunity Zone
      Legislation, 2018
    • Presentation to the Kentucky Association of Manufacturers, Annual Business Briefing, Tax Incentives for Manufacturers, 2017
    • Presentation to MainSource Bank, Kentucky State Tax Incentives, 2017
    • Tax Incentives for Manufacturers, Kentucky Association of Manufacturers Business Briefing, 2016
    • Presentation to Council on State Taxation, Mid-West Regional State Tax Seminar, Special Report: State Tax Issues Related to IRC 385 Regulations and State Tax Haven Legislation, 2016
    • Presentation to Stock Yards Bank & Trust Company, Kentucky State Tax Incentives, 2016
    • Special Report: State Tax Issues Related to IRC 385 Regulations and State Tax Haven Legislation, Council on State Taxation, Mid-West Regional State Tax Seminar, 2016
    • Kentucky State Tax Incentives, Stock Yards Bank & Trust Company, 2016
    • Sales and Use Tax in Kentucky, National Business Institute, 2015
    • Like-Kind Exchanges, University of Louisville Grief Institute, 2014
    • Limited Liability Entity Taxation and Planning, University of Louisville Grief Institute, 2013
    • Kentucky Sales and Use Tax for Manufacturers, Hitachi Automotive Products, 2013
    • 12 Tax Topics in 120 Minutes, Louisville Bar Association, 2012
    • The Fiscal Cliff, Marion County Economic Development Office, 2012
    • Let the Government Be Your Silent Partner: Tax Incentives in Kentucky, Kentucky Society of CPAs, 2011
    • Saving Green by Going Green in the Bluegrass: Kentucky Tax Incentives for Green Businesses, Greater Louisville Inc., 2011
    • Interest Charge Domestic International Sales Corporations, Greater Louisville Inc., 2011
    • Tax Credits, Government Loans, Government Guarantees, and Other Incentives Available for Businesses, SKO 22nd Annual Spring Keeneland Seminar, 2011
    • Independent Contractor versus Employee: Why it Matters, Louisville Association of Paralegals, 2011
    • Kentucky Local Occupational License Taxation, Louisville Grief Institute, 2010
    • Kentucky Economic Development Incentives: A Summary of 2009 House Bill 3 Incentives for a New Kentucky, Kentucky Commercial Real Estate Alliance, 2010
    • Ethics and the Standard of Care for Tax Practitioners: Guidelines in Practicing Tax, Louisville Bar Association, 2010
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