Leighton Regis Director of Tax Strategies

Leighton Regis, Esq., LL.M, MBA, who goes by Regis, serves as the Director of Tax Strategies at Cassaday & Company, a role he has held since July 2025. With more than a decade of experience in the tax law industry, he provides clients with sophisticated legal insight and strategic planning designed to enhance long-term financial planning.  

Working closely with Cassaday’s financial advisory and estate planning teams, Regis develops and implements tax-efficient strategies tailored to each client’s holistic financial plan. While he does not prepare tax returns, his focus on advanced tax planning strategies ensures clients receive coordinated, up-to-date, and comprehensive guidance as part of the firm’s integrated wealth management approach.  

Before joining Cassaday & Company, Regis worked as a Tax Law Specialist at the Internal Revenue Service (IRS), where he researched and translated complex tax laws, and regulations while assisting stakeholders with technical tax matters. He also held roles at KPMG (Washington National Tax) and the American Institute of CPAs (AICPA), where he advised high-net-worth clients on the tax implications of cross-border transactions and served as a liaison between CPAs and regulators, advocating for sound tax policies that benefitted taxpayers, practitioners, and the profession at large, respectively.   

Regis earned his Master of Law (LL.M) in Taxation from Northwestern Pritzker School of Law, his Juris Doctorate degree with a certificate in Taxation from St. Thomas University in Miami, and his master’s in finance from Nova Southeastern University. He is admitted to the bar in the District of Columbia.  

Originally from the Caribbean Island of Trinidad and Tobago, Regis has lived in Washington, D.C. since 2018. Outside of his professional endeavors, he enjoys traveling with his wife, Anne Caroline, and teaching his 1-year-old son, Santiago, how to dance and cheer on the Philadelphia Eagles. 

Leighton is not registered with Osaic Wealth, Inc. or Cassaday & Company, Inc., and does not offer securities or investment advisory services