Tax Controversy and Litigation

  • Holland & Knight's Tax Controversies and Litigation Team has more than a half century of experience representing both businesses and individuals in tax disputes at the federal, state and local levels.
  • Members of our team have served in significant leadership and field-level positions in both government and private sector roles.
  • Because litigation can be costly and time consuming, we attempt to resolve disputes outside of litigation whenever possible but, if litigation cannot be avoided or is determined to be in our client's best interest, we are forceful advocates and will vigorously defend our client.


At Holland & Knight, we have a nationwide network of tax controversy and tax litigation attorneys who are experienced in advising, guiding and representing clients before federal and state taxing authorities and courts. Our tax litigators, who are part of this practice, have substantial experience litigating tax cases in the United States Tax Court, the United States Court of Federal Claims, United States District Courts across the country, and the United States Courts of Appeal. The attorneys in this practice also regularly defend clients in state courts and administrative hearings. Holland & Knight represents clients on all types of tax deficiencies and refund claims involving income taxes, payroll taxes, excise taxes, franchise taxes, estate and gift taxes, property taxes, sales and use taxes, and related penalties and interest. Our objective is to resolve each client’s tax dispute as quickly and efficiently as possible. As a result of our team's efforts, Holland & Knight was awarded the most first-tier rankings in the United States in Litigation - Tax in the U.S. News - Best Lawyers "Best Law Firms" guide (2013).

When we undertake a matter, we do the following:

  • Get to know the client and, when applicable, its officers and owners in order to provide effective representation
  • Help to determine the most advantageous procedural route - settlement, conference, administrative hearing, offer in compromise or litigation – that the client should pursue
  • Guide the controversy through the process of administrative appeals and/or litigation when issues cannot be resolved at the audit level

Holland & Knight’s tax controversy and litigation attorneys have strong relationships with auditors, tax officials and public officials throughout the United States and we know how to work within the federal and state tax systems. We also work closely with tax directors, CFOs, accountants and outside auditors of our clients to ensure that all bases are covered properly and defended during the audit and litigation process.

Examples of recent engagements include:

Federal Tax Proceedings

  • Secured substantial claim for refund of wagering excise tax for a tribal casino without costly litigation by submitting a persuasive refund memorandum to the IRS
  • Reduced estate tax liability by more than $1.3 million relating to the valuation of shares of stock through the filing of an offer in compromise with the IRS
  • Defended a private foundation with approximately $400 million in assets from a possible challenge by the IRS with respect to the foundation’s structuring of its supplier arrangements
  • Achieved complete victory for client in the United States Tax Court (zero tax liability and abatement in full of original penalty assessment in excess of $100,000)
  • Secured abatement based on reasonable cause of substantially all IRS penalties throughout a six year period for a private foundation
  • Represented a client in appellate litigation in the United States Court of Appeals for the 11th Circuit (which reversed the Tax Court decision) relating to whether life insurance proceeds to be used for a redemption of shares under a buy-sell agreement were includable in valuing the corporation’s shares for estate tax purposes
  • Obtained favorable settlement for a client in litigation pending in the United States Tax Court of approximately 33 percent of the original assessment by the IRS
  • Negotiated with the IRS to refrain from a seizure of a client’s principal residence
  • Negotiated with the IRS to release a levy against an investment account of a non-resident alien client
  • Convinced the IRS to reverse its initial position to suspend a client from the IRS electronic filing system for an extended period of time
  • Represented a client in an IRS audit for multiple years relating to internal accounting irregularities and turned a potential deficiency into a refund
  • Resolved an IRS dispute for $1.1 million (with exposure in excess of $6 million) involving income tax, gift tax and various penalty issues for failure to file Forms 3520 and 3520-A by using the Fast Track Settlement process with the IRS

State and Local Tax Proceeding

  • Negotiated certain sales and use tax exemptions for a major electrical utility corporation for purchases of generation and transmission equipment resulting in a $1.5 million reduction in a sales and use tax assessment
  • Rebutted a challenge by a state of a client’s methodology for calculating and paying fuels tax, pursuant to an agreement with a trucking company, and resolved the matter prior to trial with client receiving a $3 million reduction in assessment
  • Settled a case prior to trial in favor of medical equipment manufacturer on the issue of deductibility of royalty expense and inter-company interest expense
  • Convinced the state to concede its case prior to trial in a client’s favor on the issue of sourcing of receipts from portfolio fund management for sales apportionment purposes
  • Proved at trial that a client’s appeal had been timely filed resulting in a refund of several hundred thousand dollars
  • Won a $7 million trial in a reported decision for a Fortune 500 company regarding a complicated state income tax apportionment issue

Criminal Tax

  • Defended preparers of federal income tax returns in an inquiry by the United States Department of Justice/
  • Represented a client in avoiding criminal sanctions by the IRS in a case involving a multi-year failure to file income tax returns
  • Represented a non-resident alien in a criminal investigation by the United States Department of Justice resulting in no criminal charges being filed against the client
  • Represented a client in avoiding criminal sanctions in an investigation by IRS special agents and attorneys from the United States Department of Justice

Holland & Knight’s tax controversy and tax litigation team understands that tax controversies and tax litigation raise a number of important strategic decisions from the inception of an audit through trial and appeal. For example, in many tax audits, the client may desire or need to invoke potential privilege objections under the attorney-client privilege, accountant-client privilege, work product doctrine, critical self-analysis privilege and, if applicable, the statutory privilege pursuant to Section 7525 of the Internal Revenue Code. Holland & Knight’s attorneys address the applicability of these various privileges at the beginning of any tax audit and assist the client in preserving these privileges while navigating through an audit by, or litigation against, the IRS or state taxing officials. Further, Holland & Knight’s tax controversy and tax litigation attorneys have a wide range of experience in addressing all other primary and collateral aspects of a tax audit and subsequent tax litigation including, but not limited to, Fifth Amendment and other constitutional issues, claim and issue preclusion and other estoppel matters, discovery and FOIA issues, and all other technical and substantive tax issues raised by statute, regulation and administrative pronouncement.

In addition to assisting individual taxpayers, Holland & Knight represents many other distinct types of taxpayers – including publicly traded and privately held corporations, trustees of defined contribution plans including leveraged and non-leveraged ESOPs and other ERISA plans, partnerships, limited liability companies, executors, trustees of testamentary trusts, S corporations, LLCs, tax-exempt entities, governmental entities (including Indian tribes), and all other types of clients. Our client base cuts across both geographic and industry boundaries.

Holland & Knight’s tax controversy and tax litigation team includes attorneys who previously served as prosecutors at the United States Department of Justice, attorneys with the Office of Chief Counsel of the IRS, revenue officers at the IRS, former state revenue department litigation attorneys and tax counsel to the House Ways and Means Committee. These trial attorneys have litigated hundreds of tax cases involving complex tax and legal issues. Our tax controversy and tax litigation practice also includes attorneys who have CPAs, MBAs, or Masters in Laws in Taxation.

Summarized below are examples of some other specialized areas in which our attorneys are engaged within our nationwide tax controversy and tax litigation practice:

Tax-Exempt and Government Entities

Holland & Knight has several tax controversy attorneys who focus primarily on the legal needs of tax-exempt organizations. This group regularly represents private foundations, public charities, trade associations and all other types of tax exempt organizations in audits and other inquiries by the IRS.

Holland & Knight has advised and represented certain of its private foundation clients regarding IRS claims of excessive compensation and other forms of self-dealing, failures to make the required qualifying distributions or to exercise expenditure responsibility, and violations of the excess business holdings rules. Holland & Knight also counsels certain of its public charity clients with respect to IRS allegations of excess or private benefit (e.g., unreasonable compensation and non-fair market value transactions), prohibited political activity and excessive lobbying, as well as challenges to the basis on which the organization’s exemption was granted (e.g., the community benefit standard in the case of hospitals and the community access standard for other organizations). In addition, with respect to all types of tax-exempt organizations, Holland & Knight handles audit and compliance issues related to the unrelated business income tax (UBIT) rules and employment tax compliance issues. Working with the tax-exempt bond financing specialists within the firm, Holland & Knight regularly defends both issuers and borrowers in challenges to tax-exempt financings.

Indian Tribal Governments

Holland & Knight has groups of attorneys located in Los Angeles, Washington, D.C., and several other offices that focus exclusively on the legal and tax needs of Indian tribal governments and tribal organizations. Within this context, several of Holland & Knight’s tax, employee benefits and public finance attorneys provide specialized services to tribal governments with respect to issues that are regularly examined and increasingly challenged by the IRS. These include:

  • compliance with information reporting and withholding rules when tribes make taxable payments of gaming revenues to their members (e.g., per capitas)
  • employment tax compliance matters, which include classification of workers as employees or independent contractors, FICA, FUTA and wage withholding
  • employee benefit plan compliance (both tax and ERISA matters)
  • tribal general welfare plans that involve the provision of benefits to tribal members, such as education, housing, health care and recreation
  • tax-exempt bond qualification matters, including those arising under section 7871 of the Internal Revenue Code (“essential governmental function” test applicable to tribes) and under other provisions, (e.g., private use and arbitrage)

In addition, Holland & Knight has defended the tax-immune status of tribal business entities when such issues have been raised by the IRS on audit, and regularly counsels tribes on how to structure their enterprises in a tax-efficient manner.

Estate, Gift and Fiduciary Tax Disputes

Holland & Knight’s tax litigators have extensive experience litigating federal estate, gift and fiduciary income tax disputes in federal and state courts across the country. For example, Holland & Knight has represented many corporate and individual fiduciaries, as well as charitable and educational institutions, in negotiating and litigating tax issues against the IRS in the United States Tax Court and United States District Courts. Additionally, Holland & Knight’s tax controversy and litigation attorneys regularly represent clients in audits by, and appeals against, the IRS on estate and gift tax returns, fiduciary income tax returns and other tax-related issues including domicile disputes.

Criminal Investigations and Prosecutions

Holland & Knight regularly represents citizens of the United States, as well as resident and non-resident aliens, during all phases of criminal tax proceedings including criminal administrative investigations, grand jury investigations, trials and appeals. Some of our tax litigation attorneys have spent considerable time prosecuting criminal tax cases while employed by the Tax Division of the United States Department of Justice or the offices of various United States Attorneys. Holland & Knight’s team of tax litigators use their experience to counsel clients during investigations by the IRS and Department of Justice, as well as at the state level. Holland & Knight’s tax controversy and tax litigation attorneys also work to bring clients into the tax system by utilizing applicable programs when available, such as the Offshore Voluntary Compliance Initiative or Last Chance Compliance Initiative. When these initiatives are no longer available, Holland & Knight’s attorneys are adept at helping clients to become accepted in, and navigate through, the Voluntary Disclosure program of the IRS. By assisting clients in taking advantage of such programs, they may be able to avoid criminal prosecution.

State and Local Tax

Holland & Knight’s tax controversy and tax litigation attorneys have represented businesses and individuals before state and local taxing authorities in jurisdictions across the country. Holland & Knight’s representation includes assisting clients with state and local tax audits, challenging assessments, litigating contested tax issues, seeking refund claims before administrative tribunals and state courts, and advocating our clients’ positions before state appellate courts. Holland & Knight’s tax controversy and tax litigation attorneys routinely handle matters involving state and local income, excise, sales and use, franchise, telecommunications, hotel occupancy, and fuels taxes. In the area of unclaimed property, Holland & Knight has counseled companies on multi-state escheat compliance issues, defended against state unclaimed property audits and litigated unclaimed property appeals. Many of Holland & Knight’s tax controversy and tax litigation attorneys have acted as counsel for state taxing authorities. Holland & Knight’s goal is to coordinate an entity’s state and local audit and tax litigation needs nationally, while employing a close-knit team of individual tax professionals, each familiar with his or her tax jurisdiction, to represent the entity on a local basis.

Real Estate

Holland & Knight’s real property tax assessment litigation team minimizes the real property tax liability of property owners. Holland & Knight represents property owners including institutional investors, not-for-profit organizations, REITS, and privately held entities in reviewing and appealing real estate tax assessments. Holland & Knight attorneys have experience with all types of commercial property including office buildings, hotels, apartment buildings, industrial, warehouse, and mixed use properties ranging in value to over $250 million. Holland & Knight has experience at all levels of review and appeal from the initial administrative review through trial courts and courts of appeal in jurisdictions throughout the United States. Holland & Knight attorneys have successfully and regularly obtained substantial real estate tax savings and tax refunds for its clients.

Employee Benefits

Holland & Knight’s tax controversy and tax litigation attorneys have significant experience in negotiating employee benefit issues with the IRS. Holland & Knight routinely deals with the IRS on plan audits, qualified plan determination letter applications, voluntary employee plan and fiduciary duty corrections, and pension underfunding matters. Holland & Knight’s tax litigators are well-equipped to handle complex employee benefit disputes and they regularly litigate such issues in courts throughout the country.


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