In the late 1860s, gentleman bank robber George L. Leslie arrived in New York and started working for Fredericka Mandelbaum, one of the city’s most notorious crime bosses. Leslie always claimed to have studied architecture in college and drew on his training to mastermind some of the most daring...

In 1817, Italian-born painter Francesco Mezzara had a spat with his patron, New York attorney Aaron Palmer. As the feud escalated, Mezzara painted an insulting picture of Palmer and put it up for auction. Mezzara was giddy when the picture fetched $40—but not for long. Soon, he stood accused of...