Matthew S. (Matt) Paolillo


Matt Paolillo is a partner in MendenFreiman’s tax controversy, tax planning, and business law practice areas. He has extensive experience representing clients before the Internal Revenue Service as well as various state tax authorities. His tax controversy experience includes representing individuals and businesses with respect to IRS audits, appeals, collection issues (levies, liens, installment agreements, and offers in compromise), and in U.S. Tax Court and U.S. Court of Federal Claims proceedings.

Matt also works closely with clients and CPAs in devising strategies to minimize potential taxes, penalties, and interest. He has experience  working with individual investors in connection with their participation Conservation Easement transactions, including representing investors in response to IRS requests, summonses, and subpoenas Matt’s work also involves planning and implementing intricate organizational structures on behalf of business clients, including planning for domestic and international tax compliance issues.

Prior to joining MendenFreiman, Matt was an associate at Gomel, Davis & Watson, LLP, and previously served as an Attorney Advisor to Judge Elizabeth Crewson Paris of the U.S. Tax Court.


  • Georgetown University Law Center, LL.M. Taxation, 2011
  • Wake Forest University School of Law, J.D., 2010
  • College of William & Mary, B.B.A., Accounting, 2007

Admissions and Professional/Civic Organizations

  • State Bar of Florida
  • District of Columbia Bar
  • Supreme Court of the United States
  • United States Tax Court
  • United States Court of Federal Claims
  • American Bar Association, member

Awards and Recognition

  • Best Lawyers “Ones to Watch” – 2022 -2023