Jonas Phillips Levy was the youngest of ten children born to Michael and Rachel Phillips Levy. Raised in Philadelphia, his siblings included Benjamin and Uriah Levy. His maternal grandfather, Jonas Phillips, for whom he was named was a veteran of the Revolutionary War.

Like Uriah, the younger Jonas would spend several years pursuing an adventurous life—much of it at sea—but unlike his older brother, who would become the first Jewish commodore in the US Navy, Jonas’ adventures had rather more mixed results, and his life can often read like a series of frustrations. At sixteen, he signed on as a cabin boy aboard the schooner Sygnet, on its way to New Orleans, and in the following years he worked on numerous merchant ships and steamboats.

He sailed in and out of ports throughout South and North America in the 1820s and 30s, survived an attack near Tierra Del Fuego, and received Peruvian citizenship in appreciation for the assistance he provided to the Peruvian Navy. He saved some money, and in 1836 set up a store in New York, but a year later his warehouse burned down, resulting in significant losses.

The following year he moved to New Orleans, again establishing himself as a merchant, but by 1843 he had declared bankruptcy. Later that year, Jonas moved with his brother Morton to Tabasco, Mexico, seeking his fortunes there. With the outbreak of the Mexican American War, in 1846, the Mexican government seized much his property. By year’s end, he had been ordered to report for service, and Levy purchased the transport ship American, which he commanded transporting troops to Veracruz. Following the surrender of the city, General Winfield Scott appointed Levy the port’s captain.

He soon left, however, returning to the United States, and that November married Frances Mitchell. The couple then returned to Veracruz, where their first child, Isabella, was born two years later. By 1852, they had settled back in New York where they would raise their five children. Levy spent much of the rest of his life pursuing claims against the American government for losses and expenses incurred during the war. His legal proceedings carried on into the 1870s, but he was ultimately unsuccessful.

His son Jefferson Monroe Levy would, a financier and lawyer in New York, at twenty-seven, in 1879, took control of Thomas Jefferson’s historical home, Monitcello, which his uncle Uriah had purchased in 1834. Like his uncle, he invested vast amounts of his own money in the preservation and restoration of the property, which in 1923 he sold to the Thomas Jefferson Foundation.