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Menden Freiman MendenFreiman LLP

Matthew (Matt) S. Paolillo

Senior Associate

Matt Paolillo is an associate in MendenFreiman’s tax controversy and collection, tax planning, business law, and estate planning practice areas. He joined the firm in 2019 and has experience representing clients before the Internal Revenue Service as well as various state tax authorities.

Matt also works closely with clients to develop business and estate plans that accomplish their personal goals while minimizing tax and other costs. He has experience drafting LLC and partnership operating agreements, purchase agreements, and other business contracts as well as wills, trust agreements, and other estate planning documents.

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. In his time at the Tax Court, Matt gained extensive experience in the practice and procedure of tax controversy with respect to a wide range of substantive tax issues.

“Each engagement is an opportunity to get to know a client, to assist where they have found unease or frustration, and to find a solution that allows that client to move forward with a sense of certainty and security. That is why I love what I do.”


  • 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

Bar Admissions

  • Florida
  • District of Columbia

Federal Court Admissions

  • Supreme Court of the United States
  • United States Tax Court
  • United States Court of Federal Claims

Representative Matters

  • Represented individuals and businesses in IRS audits, appeals, and administrative conferences, resulting in significant tax savings.

  • Represented individuals and businesses before the United States Tax Court, including successful settlement negotiations with IRS Appeals and IRS Counsel.

  • Successfully negotiated IRS collection alternatives such as installment agreements, offers in compromise, and “currently not collectible status” on behalf of individuals and businesses.

  • Stopped IRS collection actions, such as wage garnishments and bank levies, and successfully negotiated lien releases, withdrawals, and discharges on behalf of individuals and businesses.

  • Planned and implemented intricate organizational structures on behalf of large business clients and assisted in planning for domestic and international tax compliance issues.

Professional Affiliations and Memberships

  • The Florida Bar, member
  • District of Columbia Bar, member
  • American Bar Association, member

Awards and Recognition

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