Robert C. Webb - Frost Brown Todd LLC

Robert C. Webb

Listed in Best Lawyers since 2007
Phone: 502-568-0313

Robert has established a reputation as a litigator in civil and criminal tax litigation matters, white-collar criminal defense, and business litigation. Over the past twenty years, he has resolved thousands of civil and criminal tax matters at the federal, state and local level. Robert has worked at the Department of Justice Tax Division in Washington, D.C. while pursuing his Masters of Law (LL.M.) in Taxation from Georgetown University Law Center in Washington, D.C. Robert has taught federal taxation of entities at Bellarmine College, authored the Criminal Tax Practice Monograph for the University of Kentucky College of Law and speaks annually at the American Bar Association Criminal Tax Institute.

Robert is a member of the firm's white collar group and tax controversy and litigation practice group. He has represented taxpayers in tax controversy matters from Connecticut to California.  Robert has handled civil and criminal tax cases throughout the United States.  He regularly represents clients in civil and criminal tax controversies before the IRS and in the United States Tax Court, United States District Court and the Kentucky Board of Tax Appeals. He has led the defense of federal and state criminal offenses at the investigatory, grand jury, and trial levels in such areas as criminal tax fraud, mail and wire fraud, interstate transportation of stolen goods, criminal and civil RICO, healthcare fraud, criminal antitrust, money laundering, gambling, and environmental matters.  Robert regularly conducts internal investigations for public companies involving computer fraud and document destruction issues, and designs and implements records management systems.

Representative Matters


      • Was part of a trial team defending a former Commonwealth of Kentucky public official that obtained a Judgment of Acquittal in a highly publicized political corruption and tax fraud case.
      • Represented the owner of a construction company in a federal criminal tax trial. This involved delinquent employment taxes for a construction company.
      • Defended a CPA who was accused of conspiring with his client to commit money laundering.
      • Represented a bank president who had allegedly violated federal bank fraud statutes. This involved a bank president who was duped into loaning millions of dollars to an unscrupulous family.
      • Worked closely with Alan M. Dershowitz and John Cline in multiple federal tax fraud and money laundering trials involving a successful business man. Convinced the United States Sixth Circuit Court of Appeals to reverse a tax fraud conviction.
      • Led the pre-trial defense of the largest search warrant case in the history of Kentucky. The case involved two hundred agents who executed a federal search warrant on a ten-story office building. The Government seized all computer and electronic data. The United States District Court issued an order requiring the government to copy the documents and return them to our client. The federal agents worked twenty-four hour shifts copying and returning the business records.
      • Negotiated successful plea agreements involving mortgage fraud in which the defendants were accused of brokering millions of dollars in fraudulent residential and commercial mortgage loans throughout the United States.
      • Served as lead trial counsel in a three-day United States Tax Court trial. The case involved the ability of S-corporation shareholders to deduct losses to the extent of their stock basis. Back to back loans, economic substance and business purpose was at issue in the case. The taxpayer is a large multi-unit franchisee owner.
      • Represented a franchisee convenient store owner in a two-day hearing that required the defendants to remove Uniform Commercial Code liens that had been wrongfully filed against the store.  The liens prohibited the owner from selling his million dollar convenient store.
      • Negotiated a plea agreement for the owner of a jet aircraft transportation company who had allegedly placed millions of dollars in offshore Cayman Islands bank accounts. This involved the validity of offshore entities and the implications of offshore bank accounts.
      • Served as second chair trial counsel to a closely held company that manufactures paint and related products in a very complicated environmental crimes case.
      • Defended a multi-million dollar wholesale company in United States District Court that had been charged with diverting baby formula between California and New York.
      • Argued in the Sixth Circuit Court of Appeals for the reversal of a United States Tax Court decision, in which the Tax Court had ruled that the client had waived the affirmative defense of the statute of limitations by failing to specifically assert the affirmative defense in his United States Tax Court petition. The client had raised the defense in attachments to his petition.
      • Defended a major hospital and health care organization in an investigation involving alleged health care fraud and over billing.
      • Performed an extensive internal investigation for a public company involving potential violations of the Foreign Corrupt Practices Act and issued a full report to its chief executives.
      • Conducted an extensive internal investigation involving an alleged kickback scheme involving a public company and its subsidiaries.
      • Defended a doctor in a Medicare and Medicaid fraud trial. The government alleged that the doctor had intentionally up-coded his Medicare and Medicaid billings in order to receive more money from the government.
      • Represented a distinguished tax lawyer who was under criminal investigation by the Department of Justice Tax Division involving an alleged "Klein" conspiracy.
      • Assisted in obtaining an order, forcing tax shelter promoters to repatriate money from a Canadian bank account.


      • Represented multiple individual and corporate taxpayers through the state audit and appeals function, before the Kentucky Board of Tax Appeals and in state court.
      • Negotiated the complete abatement of a multi-million dollar intangible property tax assessment against a publicly traded company.
      • Resolved a motor fuels excise tax assessment against a fuel distributor in excess of $1,000,000 for $5,000.
      • Resolved a multi-million dollar tangible property tax assessment against a publicly traded biotech company and worked to enact a legislative exemption for certain biotech property.
      • Resolved a multi-million dollar tangible property tax assessment against a publicly traded metals producer.
      • Resolved a significant sales and use tax assessment against a manufacturer of environmental equipment.
      • Resolved a significant Louisville Metro Occupational License Tax assessment against an out of state investment partnership.
      • Resolved a substantial local insurance premium tax assessment against a national insurance company.
      • Resolved a substantial utility gross receipts license tax assessment against a publicly traded manufacturing company.


    • I have structured a cutting edge equine syndication related to breeding and racing activities.
    • Defended a horse breeder in an Internal Revenue Service audit. 
    • Defended an equine breeder in a hobby loss case relating to his farming activities.   
    • Currently in the process of pursuing a civil RICO claim against ClassicStar and its principals relating to a thoroughbred mare lease arrangement.
    • Currently defending taxpayers from around the country in equine-related Internal Revenue Service audits relating to passive activity losses, at risk limitations, and Internal Revenue Code Section 162 deductions.

University of KentuckyBS 1985University of Louisville, Louis D. Brandeis School of LawJ.D. 1988Georgetown University Law Center
Legal Aid Society CampaignAssociation of Trial Lawyers of AmericaNational Association of Criminal Defense LawyersKentucky Bar AssociationLouisville Bar AssociationKentucky Council on Economic EducationNational Institute for Trial Advocacy (NITA)American Bar AssociationDistrict of Columbia Bar Association

Office Location

400 West Market Street, Suite 3200
Louisville, KY 40202-3363
United States

Lawyer of the Year Awards

2013 Lawyer of the Year in Litigation and Controversy - Tax of the Louisville Metro Area
Robert C. Webb has earned a Lawyer of the Year award for 2013!

Practice Areas

Litigation and Controversy - Tax