[2] Leary started his career in the counting house of Bache McEvers, a prominent shipping merchant who was president of the New-York Insurance Company and a brother-in-law of Minister Edward Livingston.
"[1] Before the outbreak of the U.S. Civil War, Leary owned one of the largest lines of merchant sailing vessels in the United States, which made him and his brothers a fortune.
Leart was known as a "Beau Brummell in society when the fashionable world centered about Washington Square," and was one of McAllister's original Patriarchs.
[1] Leary was a lifelong bachelor who had his sister, Annie, accompany him to society functions in New York City as well as Newport, Rhode Island (he occupied the Paul cottage).
[7] After his death, his sister Annie was the executrix of his estate,[8] and inherited his fortune as well as his social prominence, using his wealth to become a philanthropist (mostly to Catholic causes) and earning her the title of Papal Countess from Pope Leo XIII, the first for an American woman.