Once qualified as a barrister, Benjamin chose to join the Northern Circuit, as it included Liverpool, where his connections in New Orleans and knowledge of mercantile affairs would do him the most good. In an early case, he defended two former Confederate agents against a suit by the United States to gain assets said to belong to that nation. Although he lost that case ("United States v Wagner") on appeal, he was successful against his former enemies in "United States v McRae" (1869). He had need of rapid success, as most of his remaining assets were lost in the collapse of the firm of Overend, Gurney and Company. He was reduced to penning columns on international affairs for "The Daily Telegraph".