African American Outlaws in America
The outlaw is an archetypal figure in American folklore. His brand of criminality, his appearance, and the landscape in which he operates all combine to create a perfect storm of Western legend. In the public imagination, outlaws are synonymous with train robbers and bank robbers. But while these high-profile crimes often receive the most press attention, there were thousands of lesser known black-market operators who operated throughout the United States during the late 19th and 20th century.
Black market activity is a universal human phenomenon that reaches back as far as our recorded history. Organized crime has always thrived in economically depressed areas where opportunity is scarce, but greed is abundant.
In the late 19th century, Isom Dart, an enslaved from Arkansas, rose to notoriety as a Wyoming outlaw. He was nicknamed “Calico Cowboy,” “Tan Mex,” and “Black Fox,” among other names. At age twelve, Ned Huddleston, a Confederate fighter, led him to Texas to steal food and provisions for the military. When Ned returned to Arkansas when the war finished, he was set free. After traveling throughout the west, Huddleston was released and then he joined the cowboy life.
During his journey to Texas, in Huddleston worked as a cook in a camp at the Carmicle railroad in Wyoming Territory close to Rock Springs, in Wyoming, near a coal mine and railway station. Railway stations and coal mining were common in the area, which had a saloon population and outlaws. Because of the racial bias of the time, they dubbed him “Nigger Ned.” Quick Shot, one of many Wyoming desperado nicknames, would soon be bestowed upon him after he shot his six-shooter and left five decapitated birds in a Green River meadow.
The sight of traders, hunters, and trappers passing the camp made Huddleston depart. He went as far south as the border of Texas-Mexico, where he performed rodeo tricks and stunts before working as a bull rider. He also became a horse and cattle thief, which was lucrative than his earlier jobs. He smuggled cattle and horses through the Rio Grande into Texas, sold them, and stole them. Huddleston purchased a ranch nearby Brown’s Hole (also called Brown’s Park) in northwest Colorado, adopted the name Isom Dart, and started a relationship with a Shoshone lady. Instead of staying outlaw, Dart became a bullfighter and rancher, although he was drawn back into the wildlife with gambling, fighting, and law encounters. He joined the Tip Gualt Gang that was full of outlaws and went back to cattle rustling.
The Brown’s Park range war was raging in full force in 1899, pitting the Snake River Stock Growers Association and the Two-Bar Ranch Cattle Company against smaller cattlemen. Dart joined Ann Bassett, called “Queen Ann,” who owned the Bassett Ranch and ran it as a cattle rustler. Dart stole cattle from the Two-Bar Company. Small ranching operations in the Brown’s Park area were becoming bored with rustling activities and so hired disreputable range investigator Tom Horn to drive them away. On October 3, 1900, Horn shot dead Isom Dart, aged 51, living near Routt County, Colorado, nearby North Highway 72, after he strolled outside his cabin.
In the early 1920s, New York entrepreneur Casper Holstein was a notoriously known mobster who was particularly known for the Harlem gambling ‘numbers rackets’. He revived illicit gambling in Harlem after it had been dormant for several years following Peter H. Matthews’ imprisonment in 1915, along with a number of other rivals, most notably Stephanie St. Clair.
Born in St. Croix, Danish West Indies (now the US Virgin Islands), Holstein relocated to New York with his mother in 1894. He was educated at a Brooklyn high school until he graduated. Holstein had a brief stint in the navy prior to the Spanish American War. He started doing various odd jobs in Manhattan once the war was done. At some time in his career, he worked as a messenger on Wall Street.
Holstein grew familiar with the stock market on Wall Street. Additionally, he started learning the numbers system, which is an an illegal lottery frequently played by the poor residents of the city. Eventually developed into his own lottery that he termed Bolito. In the early 1920s, the New York underworld acknowledged Holstein as the ‘Bolito King’. By the middle of the 1920s, he was running a prosperous lottery, employing his lottery winnings to live an extravagant lifestyle. He owned a mansion on Long Island, a collection of high-end vehicles, and several thousand acres of farmland in Virginia. He also owned two apartment buildings in Harlem.
To gain the support of the African-American community, Holstein started supporting worthy causes and donated a percentage of his ill-gotten gains to humanitarian organizations. He bankrolled dorms and student houses at Southern black colleges and increased the income of the Harlem Renaissance artists and helped the underprivileged youngsters of Harlem. He donated part of his proceeds from the lottery to the construction of a Baptist school in Liberia as well as funding a museum in New York and storm disaster relief for the U.S. Virgin Islands, his native country.
Holstein had become the most important power broker in Harlem by the end of the 1920s. Under his control was many numbers-running operations, nightclubs, and other legal enterprises. It is said that he earned nearly $12,000 a day. The New York Times mentioned that Holstein was Harlem’s favorite hero and was widely known for his wealth, sporting interests, and philanthropies among the people of his race. In 1928, Holstein was held hostage by five white men for a ransome of $50,000 ransom. He was released three days later. There was no arrests or ransomes paid. Famous New York mobster Dutch Schultz, was said to be behind Holstein’s abduction. Holstein “retired” from number running after serving a year in prison for unlawful gambling, and he then devoted the rest of his life to assisting other causes.