Despite her family's background (both her stepfather and husband were officers of the Royal American Regiment) Theodosia aligned herself with the Patriots, counting William Livingston and Robert Troup as friends and allies.
During the war, with her estate technically being owned by her husband, it was at various times under risk of confiscation as Loyalist property; her powerful friends, allies and patrons, including Livingston and William Paterson, ensured the case was halted.