Our Team

Anthony P. Kupersmith

Tony’s practice focuses on real estate, land use, and zoning law.  Tony leverages his past experience as County Attorney for Talbot County, Maryland to help clients navigate legal hurdles to achieving the best use of their land.  As County Attorney, Tony was the chief legal adviser to Talbot County and, in this capacity, represented the County Council, County Departments, and Boards and Commissions in all legal matters. 

Tony takes a collaborative approach to transactions, but does not hesitate to litigate in order to protect key rights.  Tony’s government experience allows him to understand how policy decisions affecting the use of land are made, and, in turn, to advocate effectively on behalf of clients.  Tony’s practice extends to the related areas of administrative, agricultural, condo, and homeowners associations, construction, and environmental law. 

Tony graduated with honors from William and Mary Law School in 2012 and clerked for Judge Broughton M. Earnest on the Circuit Court for Talbot County, Maryland, before joining Talbot County Government as an Assistant County Attorney in 2013.  Tony was appointed County Attorney for Talbot County in 2017, a position he held until joining McAllister, DeTar, Showalter & Walker.  Prior to law school, Tony worked as a Congressional aide on Capitol Hill and an analyst for a major defense contractor. 

Tony is an avid boater and fisherman.  Tony grew up in Northern Virginia, but fell in love with the Chesapeake Bay and the Eastern Shore at a young age, hunting with his father on the Sassafras River and competing in local sailing regattas up and down the Bay.  Tony, his wife, and their two children currently reside in Annapolis where they enjoy cruising local waters in the family Boston Whaler, attending festivals and Navy sporting events, and cycling the B & A Trail.


  • What’s Up? Anne Arundel County & Central Maryland Leading Lawyer: Environmental Law, 2022-2023
  • What’s Up? Anne Arundel County & Central Maryland Leading Lawyer: HOA/Condominium Law, 2022-2023
  • What’s Up? Anne Arundel County & Central Maryland Leading Lawyer: Real Estate Law, 2022-2023
  • What’s Up? Media: Up & Coming Lawyers 2023