In 1856, Mary Ann Brown Patten became the first woman to successfully sail a clipper ship around Cape Horn through the notoriously treacherous waters at the tip of South America. Schooled in navigation by her husband, Joshua Patten, the captain of Neptune’s Car, she took charge of that San Francisco–bound vessel after her husband was incapacitated by tuberculosis and the ship’s first mate was imprisoned for insubordination. Only nineteen years old and pregnant at the time, Patten brought the ship safely to its destination, earning international renown for her heroism under extraordinary circumstances. This portrait was made following that voyage.