Inevitably prior to the abolition of slavery in 1833 several of Freshfield's wealthier clients owned estates in the Caribbean and so conflicts arose with his anti-slavery convictions. Marriage settlements could be administered by solicitors over more than one generation, and it was as a trustee of one such settlement that Freshfield and his fellow trustee Alexander Baillie found themselves in 1827 temporarily the owners of fifteen slaves from an estate on Union Island. In one instance the firm tried to claim unpaid legal fees through the government scheme set up to compensate owners after abolition. Such situations have led to allegations that Freshfield profited from slavery in spite of his principles.