Benjamin is a lifelong resident of Anne Arundel County with deep family ties to Annapolis. Benjamin is the son of Annapolis attorneys, Darrell L. Henry and the late Mettie M. Smith.

Benjamin graduated from University of Maryland Francis King Carey School of Law and from Stevenson University with a B.S. in Paralegal Studies. He is admitted to practice in Maryland.

Starting in 2013, Benjamin was an undergraduate intern with a local Annapolis firm, Rex S. Caldwell, III, P.A.. Benjamin continued to work for Rex S. Caldwell, III, P.A. until being hired as an associate attorney in 2018. After Mr. Caldwell’s passing in early 2019, Benjamin became a member of Henry & Smith, LLC, another law firm in Annapolis. Benjamin continued with Henry & Smith, LLC for over a year prior to joining Hyatt & Weber. Benjamin is also former counsel to the City of Annapolis Board of Appeals, Historic Preservation Commission, and Planning Commission.

In his spare time, you will find Benjamin spending time with his family, exploring the outdoors, out on the baseball diamond, or working various automotive and household projects. Benjamin is a graduate of St. Mary’s High School and currently resides in Edgewater.