His real name unknown, The Pirate known as Diabolito (or "The Little Devil"), was born in Cuba (then under Spanish Control). Possibly born in the early 19th Century, he was considered a "Modern Era" Pirate. So prolific was Diabolito, that it was his raiding that caused then US President James Monroe and The US Congress to create America's first "Anti-Piracy" Laws. Further, he helped to initiate the famed US Naval Squadron known as "The West Indies Squadron", specifically created to fight Pirates. The Squadron would continue with it's Mission for almost 100 years.
Diabolito concentrated his attacks off The Coast of Florida, and the 90-mile area of Sea between Cuba and America. His ruthlessness was speculated to have been culled during The 2nd Barbary Wars, as well as The War of 1812. Eventually running afoul of The US Navy, Diabolito and 70 of his crew would escape capture. Making their way back to Cuba, it was thought that The US Navy, would stop their pursuit. They didn't. Following him into the Cuban Jungles, some say that Diabolito was killed in combat (rather than surrendering). Others say that Cuban Authorities were responsible.