Last month, I posted about a book about William Richard "Billy" Wilkerson, who founded The Hollywood Reporter and the Flamingo Hotel in Las Vegas. The Man Who Invented Las Vegas, written by his son, W.R. Wilkerson III, focused on Wilkerson’s Flamingo Hotel project. I wanted to learn more about how Wilkerson built The Hollywood Reporter and his other Hollywood businesses, so I read Hollywood Godfather: The Life and Crimes of Billy Wilkerson, also by W.R. Wilkerson III.

Billy’s dad, William Richard Wilkerson Sr., was a prolific gambler and alcoholic who passed out drunk after gambling while Billy was being born in 1890 in Nashville, Tennessee. He physically and verbally abused Billy, his only child, to the point where Billy’s mother, Mary, transferred him to a school run by Benedictine monks in Alabama. Billy flourished in the religious environment and transferred to Mount St. Mary’s prep school in Maryland in 1904. When Billy declared his intention of studying for the priesthood, his father went ballistic. He forced Billy to attend medical school.

In 1912, his father died, and Billy, who had failed almost half his courses that year, dropped out to support himself and his mother. He also married Helen Durkin that year. Billy started working at Lubin Manufacturing Company, which produced low-budget comedic shorts in Philadelphia. Lubkin shuttered five years later, and in 1916 Billy began managing a New Jersey nickelodeon his medical school friend had won in a bet. Billy renovated the nickelodeon to appeal to the highest-end customers so he could charge the highest prices. Within six months, it was doing well, and Billy bought a Ford Model T.

Billy was drafted for World War I in 1917, but during his medical exam, the doctor left the room to take a call, leaving behind Billy’s personnel record. Billy swiped it and bolted. With no record of him ever being in the Army, he never reported for service. When the 1918 influenza pandemic struck, it decimated the nickelodeon’s business. Billy quit and started working for Universal Studios delivering movies to nickelodeons. He was promoted to district manager of film distribution in Kansas City. Helen stayed in New York and Billy split his time between the two cities. In 1920, Billy returned to find Helen had left him for another man. After eight years of marriage, Billy was devastated. In 1921 he quit his job and traveled Europe to escape his grief. In 1922, he started working for what would later become Paramount Pictures as a film salesman. This job sent him on sales trips to Hollywood, where he saw the early beginnings of the film industry’s migration from New York City to this new location.

Billy was restless by the end of 1923. In 1924 he held several jobs in the industry, and in 1925 he started selling ads and writing for Film Daily, the main motion picture trade paper. The owner was a tyrant, and Billy missed being his own boss and keeping some of the profits he generated. He wanted to own a film studio, so in 1926 he took a train to Hollywood. Using a fake-it-till-you-make-it approach, Billy convinced popular actor/comedian El Brendel to star in the movie he and his friend Joe Pasternak would produce. Billy shopped the film to studios in New York, but they were controlled by autocratic moguls who “rivaled robber barons.” Billy failed to convince the studios. Wilkerson Studios never got off the ground.

To make money, Billy opened a speakeasy in November 1926 to fill a gap he saw in the Prohibition-era market. His operation was high class but illegal. By February 1927, he opened a second one and charged a $1,500-per-person initiation fee. He paid off police and DAs and worked with the mafia and Joe Kennedy to get his liquor supply. He did such a great job that James Walker, mayor of New York City, asked Billy to manage his speakeasies for 45% of the profits. Billy was making $1 million per year, although he lost much of that in the backroom card games he hosted. He also started dating Edith Goldenhorn, the 25-year-old daughter of his ethically challenged lawyer. Billy, then 35, married Edith in Las Vegas in June 1927. When he returned, his speakeasies were raided, which spooked him. He immediately quit the speakeasy business for good.

Billy was still resentful about his film and believed Jewish studio heads didn’t give him a chance because he wasn’t Jewish. He took the rejection personally and wanted revenge. His time at Film Daily taught him that trade papers could be powerful, and he decided to start the first daily trade paper for the Hollywood motion picture industry. In February 1929, he acquired 50% of a faltering Manhattan trade paper. He turned it around and sold the paper seven months later, pocketing $20,000. He borrowed $25,000 from a loan shark and bet the combined $45,000 on a single company in the stock market. It was October 29, 1929, better known as Black Monday. Forty-five minutes after his purchase, the market crashed. Billy was wiped out. Unable to pay the loan shark, Billy, Edith, and Billy’s mother Mary drove cross-country to start over in Hollywood.

Little did Billy know that his decision to start a trade publication in Hollywood would change his life and the movie industry forever.