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  1. Capabilities

Tax Controversy & Criminal Tax

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  • Overview

Key Contacts

James N. MastracchioSusan Elizabeth SeabrookRichard Weber
View Our Full Team

Resources

Tax Impacts

Our Tax Controversy attorneys advise and represent clients in every aspect of federal and state tax investigations, as well as the criminal tax enforcement process. This includes the Internal Revenue Service’s (IRS) multi-jurisdictional examinations and administrative appeals, U.S. Competent Authority representations, post appeals mediation, and trial court and appellate litigation in every federal court hearing a tax matter.

We provide technical experience and a strategic approach to resolving difficult and sensitive tax matters at the earliest stage possible. We have decades of experience successfully resolving domestic and international tax issues for clients, and our team includes former government trial counsel, former government prosecutors, the former IRS Chief of Criminal Investigations, and technical advisors with prior Big Four experience.

Our team approach and combined experience give our lawyers unsurpassed ability to resolve matters with tax authorities across the U.S. and around the world. We routinely present complex tax disputes in a straightforward and goal-oriented manner at the administrative stage, and have the breadth and depth of experience to do the same before judges and juries at trial. 

Key Contacts

James N. MastracchioSusan Elizabeth SeabrookRichard Weber
View Our Full Team

Areas of Focus

We regularly represent clients in state and IRS examinations. This work includes responding to Information Document Requests and consulting with taxpayer representatives to develop strategies for effective auditor coordination to obtain the best outcome for our clients. We often provide this representation in complex, multi-issue cases where special care is required in presenting the facts and law to taxing authorities. Our work frequently includes direct representation of the client with the auditors on issues that require argument and/or negotiation.

We have successfully presented, negotiated, and resolved hundreds of cases with IRS Appeals offices nationwide, and the scope of our appeals practice covers virtually every taxpayer-contested issue. Our extensive experience, and the manner in which we have handled our cases, has given us significant credibility with the team chiefs in Appeals offices around the country. We also have successfully worked with the IRS on Post-Appeals Mediation to obtain favorable dispute resolutions for our clients.

We assist clients in resolving cross-border tax disputes and evaluate the procedural options offered by the U.S. and foreign country Competent Authorities. We have played significant roles in the interpretation of intergovernmental agreements (IGAs) and treaty protocols in connection with tax investigations and have substantial hands-on experience concerning Competent Authority cross-border, information-sharing practices. Representative issues include the proper limits on the transfer of data, treaty and protocol definitions, and opportunities for dispute resolution through the Mutual Agreement Procedure (MAP). Recent cases have involved the U.S. Competent Authority and the competent authorities of Australia, Canada, the Cayman Islands, Ireland, Singapore, South Korea, and Switzerland.

Tax authorities worldwide are increasingly coordinating efforts when investigating and prosecuting tax offenses. Our criminal tax defense practice includes one of the few tax attorneys in the U.S. who has served as lead counsel on international criminal tax cases. These representations have included defending publicly traded companies, boards of directors, and senior management facing criminal investigations and prosecutions for alleged tax violations. For multi-jurisdictional investigations and litigation, we advise clients on treaty interpretation, IGAs, tax information exchange agreements (TIEAs), Competent Authority proceedings, summons and subpoena enforcement, and other U.S. and intra-governmental investigatory procedures.

If a matter proceeds to litigation, our tax controversy team includes attorneys who began their legal careers clerking in the federal courts that handle tax cases and litigating tax cases for the government. The experience gained litigating on behalf of the government, and subsequently in private practice, offers the client a first-chair trial attorney, who also has years of experience as a tax lawyer. The firm prides itself on the extensive trial and court of appeals experience and the reputations of our tax controversy attorneys.

We incorporate our prior government experience and unique insights into global audit procedures and evolving tax compliance issues to advise clients effectively on U.S. tax planning and compliance. We have particular experience with tax compliance matters and can leverage deep connections with the IRS, DOJ and other domestic and international regulators on supervision and enforcement matters to counsel clients. We have experience appearing before regulatory bodies and competent tax authorities in numerous countries and have advised foreign financial institutions and foreign governmental agencies on the implementation of the Foreign Account Tax Compliance Act (FATCA).

As governments across the globe increase their tax enforcement efforts, we are routinely coordinating multi-jurisdictional audits for our clients. From ensuring privilege and confidentiality protections are maintained to assisting with treaty interpretation matters, we are uniquely qualified to resolve cross-border issues. We have handled disputes involving the competent tax authorities of many countries worldwide, and our deep contacts, along with our foreign office presence, enables us to provide a robust and strategic defense to any multi-governmental investigation.

[Winston & Strawn’s Tax Controversy attorneys have a] unique strength in the area of representing financial institutions, including insurance companies; the controversy team understands the non-tax regulatory issues facing its clients and this helps them resolve tax issues.

Legal 500 US 2024

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Resources

Tax Impacts

Notable

Ranked Tier 3 in Tax: Contentious

Legal 500 USA 2024

Ranked Tier 3 Tax in Illinois

Chambers USA 2024

Ranked Tier 1 Nationally in Tax Law

Best Law Firms® 2025
Legal 500 USA 2024

Ranked Tier 3 in Tax: Contentious

Chambers USA 2024

Ranked Tier 3 Tax in Illinois

Best Law Firms® 2025

Ranked Tier 1 Nationally in Tax Law

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November 7, 2024
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