Matthew S. Reddington

Matthew Reddington represents businesses and individuals in complex tax controversies and litigation. He focuses on defending clients in disputes with the Internal Revenue Service and state taxing authorities, delivering strategic solutions that protect financial interests and minimize risk. Known for his ability to navigate high-stakes tax matters, Matthew provides strong advocacy in cases involving captive insurance arrangements, research and development tax credits, accounting method changes, intermediary transactions, fraud allegations, real estate issues, foreign income exclusions, and interest abatement.

Matthew approaches every case with precision and determination, ensuring that clients receive the most effective representation possible. He is recognized for taking cases beyond the United States Tax Court when necessary and presenting them before a jury, a strategy that often leads to favorable outcomes. His ability to challenge agency assumptions and control the narrative makes him a sought-after attorney for tax litigation.

Before joining private practice, Matthew served for nearly a decade as a Senior Attorney in the IRS Office of Chief Counsel. This experience gives him unique insight into IRS procedures and litigation tactics, allowing him to anticipate challenges and develop proactive strategies. During his tenure, he earned multiple awards for trial success and contributed to large-case litigation as both a team leader and a team member.

Matthew’s track record includes securing a unanimous jury verdict for a captive insurance manager in a multimillion-dollar penalty dispute, obtaining summary judgment in a research credit case, and negotiating settlements that saved clients significant amounts. His results-driven approach reflects a commitment to excellence and a readiness to fight for clients when the stakes are highest.