For over 20 years, Alejandro Guadarrama has advised corporations, financial institutions, partnerships, estates and individuals in a wide range of tax controversy and litigation matters. His practice is focused on handling high-stakes and complex IRS audits, administrative proceedings and tax litigation.


Mr. Guadarrama counsels clients on every aspect of tax litigation and coordinates all facets of complex e-discovery and cross-border discovery. He routinely performs fact-finding and analysis in connection with multilayered tax matters and helps clients navigate both legal and practical considerations of pre-litigation and litigation work.

Notable tax litigation experience includes:

  •, Inc. in its victory in one of the largest transfer pricing cases in decades and the first involving e-commerce. U.S. Tax Court (2017)
  • Massachusetts Mutual Life Insurance Company in a trial involving the proper federal income tax accounting treatment of aggregate guaranteed dividends, decided in the taxpayer’s favor. U.S. Court of Appeals for the Federal Circuit (2015) | U.S. Court of Federal Claims (2012)
  • Mylan, Inc. in securing a favorable settlement for a client ahead of litigation in a case relating to the tax characterization of the disposition of an interest in certain intellectual property. U.S. Tax Court (2018)
  • Wells Fargo & Company in a three-week jury trial involving a foreign tax credit dispute with the IRS arising from a $1.25 billion cross-border transaction with Barclays PLC. U.S. Court of Appeals for the Eighth Circuit | U.S. District Court, D. Minn. (2017)

Mr. Guadarrama is also actively involved in Skadden’s Latinx Affinity Network and is a proud member of its steering committee. In addition, he works on numerous pro bono engagements, and is a co-leader of Skadden’s Immigration Impact Project. In 2017, he received the Pro Bono Volunteer of the Year award by Ayuda, a nonprofit organization serving vulnerable immigrants throughout Washington D.C., Maryland and Virginia.

Current and significant pro bono representations include:

  • Secured the denial of the Virginia Department of Corrections’ motion to dismiss a case challenging the state’s use of solitary confinement in prisons. The case was brought on behalf of Nicolas Reyes, a native Spanish speaker who was held in solitary confinement for more than 12 years. (Reyes v. Clarke)
  • Amicus brief to the Inter-American Court of Human Rights to raise awareness of the dire situations faced by labor unionists in Guatemala over many decades, as well as the state’s failure to protect their human rights. (Gómez Virula and Others v. Guatemala)



  • LL.M., University of Miami School of Law, 1999
  • J.D., Universidad Catolica Andres Bello, 1997


  • New York
  • District of Columbia
  • U.S. District Court for the District of Columbia
  • U.S. Tax Court
  • Venezuela


  • Member, Hispanic National Bar Association
  • Member, Hispanic Bar Association of D.C.
  • Member, American Bar Association Section of Taxation
  • Member, DC Bar Taxation Community


  • English
  • Spanish

Alejandro Guadarrama