November 5, 2025
By Tom Chorneau
Most students of the Chicago beer wars of the 1920s are probably aware that Al Capone’s oldest brother was a celebrated prohibition agent. What is less well-known is how the world came to learn that Richard “Two Guns” Hart was also Vincenzo “James” Capone.
The oldest of Gabriele and Teresa Capone’s nine children, Vincenzo was born in Naples before the family immigrated to New York in 1895. He was different right from the start. He wanted to be called Jimmy and spent whatever pocket money he had going to the movies. He loved westerns. His favorite star was William S. Hart, and he fantasized about one day becoming an actor in Hollywood. Uninterested in the culture of the streets, which had thoroughly absorbed several of his younger brothers, Vincenzo instead to spend his free time at Coney Island, visiting the farm animals and especially the horses.
Vincenzo left New York at age 16 and made his way to the Midwest, where he worked a number of odd jobs, including at one point, as a stagehand for a circus. He served in the Army during World War I, came home, and married a Nebraska girl in the fall of 1919. By then, he was going by the name of Richard James Hart.
One of the first notices of him in the press as a Nebraska lawman came in October 1923 after he fatally shot a bootlegger during a car chase. The violent nature of the incident apparently even startled the rough sensibilities of the frontier denizens and led to an indictment on manslaughter. The charges were later dismissed. It was not long afterward, however, that reporters began calling him “Two Guns Hart.”
In a nod to his boyhood heroes, Hart dressed like a circus cowboy. He had a pair of pearl-handled pistols that hung heavy off his hips. He liked denim jeans and wood-button shirts. Best of all was his 10-gallon hat that stood out in almost any crowd.
Hart was no dilettante and backed his flamboyant outfits with prolific enforcement of the temperance laws. In just one month during 1925, Hart confiscated more than 100 stills, 600 gallons of mash, and 50 gallons of distilled liquor. He was credited with capturing 20 killers of Native Americans; one of them surrendered without a fight after hearing that Hart was on his trail. In the summer of 1927, he was asked by his superiors in Washington to serve as a guard for Calvin Coolidge when the president and his family vacationed in North Dakota.
Meanwhile, Big Al was simultaneously transforming himself into the nation’s first celebrity criminal. Using violence and political payoffs, Capone organized the nation’s largest crime families that would go on to dominate the underworld for decades to come.
That such a boss would not have been aware of his big brother’s exploits seems unlikely. The Capone mob had extensive business interests in Omaha, which was only about 100 miles south of the town of Homer, where Hart lived and at one point served as its town marshal. Hart also had enough of a following in Omaha that a young couple once drove out to Homer simply so that he could perform their marriage ceremony.
There are conflicting accounts of how Hart reunited with his brothers. Some news reports suggested that it took place in the mid-1930s, others have it happening as much as 10 years later. Most likely, it took place after Hart retired from law enforcement, which was around 1939. By then, he was diabetic, penniless, and nearly blind.
Al was out of the picture by then. He had been convicted in 1931 of tax evasion and was sentenced to 11 years in federal prison. He was paroled in 1939 after being diagnosed with syphilis of the brain. He moved to Florida as his mental capability diminished and died in 1947.
Although he never rose to the top of the Chicago Outfit, Ralph ‘Bottles’ Capone took control of the family’s interests following Al’s demise. He was the second-oldest Capone brother and got his nickname after running the gang’s soft drink business. It was Ralph Capone that Richard Hart reached out to in his time of need.
Bottles quickly embraced his older brother, putting him on the payroll and moving a Wisconsin hotel and bar under his name. It wasn’t all about family loyalty. Bottles had tax issues pending, and the opportunity to shroud mob ownership of place was a fortuitous turn he took advantage of.
Bottles had a long history of tax problems that predated those of his more famous brother. Bottles was, in fact, the first Capone to be targeted by Treasury investigators. In September 1928, liens valued at $11,172 were placed against his property for failing to pay income taxes. As part of that case, agents also warned Big Al that he would face the same fate if he didn’t pay up too.
Surprisingly, the mob bosses running the illegal liquor trade were not universally opposed to paying income taxes. According to a report from the federal revenue department, some 4,800 bootleggers in Louisiana paid income taxes in 1923, ranging from $82 to $10,000. The Chicago Tribune reported in September 1925 that Johnny Torrio, then the head of the Chicago mob, paid an income tax of $764 the year before. Other well-known Chicago mobsters also chipped in: Maxie Eisen paid $63, Frankie Lake paid $157, and Hirschie Miller paid $2,241.
Credit for getting the Chicago hoods to comply with the tax mandates was largely given to one agent, Eddie Waters. Waters was known to boldly storm into Chicago speakeasies and gambling dens, lecturing the bosses and their soldiers on their duty to share some of their illegal spoils with Uncle Sam, recalled Elmer L. Irey, who led the enforcement unit of the U.S. Treasury Department from 1919 until 1943. “Occasionally he would succeed, believe it or not,” wrote Irey in a syndicated column published in 1948.
Bottles was one of Waters’ key targets. According to Irey, agent Waters repeatedly tried to get Bottles to pay up, and repeatedly the mobster would make some excuse. “Aw, Eddie, it’s so much work filling out them things,” Capone reportedly said.
Waters told Capone he would fill out the forms himself and got Bottles to admit earning $20,000 by gambling. Waters went back to the office, calculated the tax, and brought the forms back to Capone to sign. “He owed $4,065,” Irey recalled. “Chicken feed. If Ralph had not been such an inveterate chiseler, he would have paid it, and neither he nor a long and distinguished group of hoodlums, including his brother Alphonse, would have gone to jail.”
But, of course, Bottles didn’t pay up, and after the liens were placed against all of his properties the feds could find in 1928, the mobster was convicted of tax fraud in June 1930 and sentenced to three years in prison. Al Capone wasn’t indicted on tax charges until a year later.
Tax problems continued to follow Ralph Capone well into the 1950s. After a three-year investigation, an administrative complaint was filed against Bottles Capone in March 1951 for tax evasion. Meanwhile, the U.S. Attorney brought the case before a grand jury a few months later. The mobster’s properties in Wisconsin were of greatest interest. Among the dozens of witnesses subpoenaed to testify was Richard James Hart, who had been identified by the feds as Vincenzo “James” Capone.
Prosecutors pressed Hart on the ownership of the lodge in Mercer and whether his brother Ralph had financed its purchase. Hart insisted he was the owner and used his own money and money his mother had given him to buy the property. When Hart emerged from the jury room, reporters were waiting.
“Until issuance of the subpoena, persons close to the Chicago underworld never dreamed that Ralph and his notorious brother, the late Scarface Al Capone, had another brother named James,” a reporter for the United Press wrote in an urgent dispatch that sparked headlines all over the country.
After the trial, Hart and his wife returned to their home in Homer, Nebraska. She apparently never knew his real name, nor did any of their four sons. One of his neighbors said that he suspected Hart wasn’t his real name, but otherwise, no one made much fuss over him.
When asked by a reporter if he intended to keep his alias, Hart shrugged. “I certainly am,” he answered.
Barely a year after testifying before the grand jury, Hart died of a heart attack in October 1951.
Tom Chorneau spent nearly thirty years as a journalist, including more than a decade as an investigative reporter and in his recent book Mrs. Cook & the Klan, Chorneau sheds new light on an unsolved murder of Myrtle Underwood Cook in the small farm town of Vinton, Iowa.