By this time
Prohibition was in full
force and effect and Miller entered the bootlegging trade. He was fined
for bootlegging in Sioux Falls,
South Dakota in October 1925, but
continued the lucrative trade. Miller then moved to St. Paul, Minnesota, and Chicago where he began his
association with underworld gangs. Coming into contact with all kinds of
unscrupulous characters he soon became a freelance gunman for a number of
Midwest bootleggers and racketeers. He was indicted on February 3, 1928
for the murder of a Minneapolis police officer, but the case was
eventually dropped from lack of evidence.
In 1930, after a friend of his was
killed by Al Capone's men, Miller tracked down three of the suspects and
gunned them down in June in what later became known as the Fox Lake
Massacre. That same year, he teamed up with other gangsters -- Harvey
Bailey, Thomas Holden, Francis Keating, George "Machine Gun" Kelly and
three others in a daylight raid resulting in the theft of $70,000 from a
bank in Willmar, Minnesota on July 15, 1930. Less than a month later, on
August 13th, in an argument over a "double-cross" from the bank robbery,
Miller killed Frank "Weinie" Coleman, Mike Rusick and "Jew" Sammy Stein
and dumped their bodies at White Bear Lake. The next month on September 9, 1930, Miller participated with Bailey, Holden,
Keating, Kelly and Lawrence De Vol in stealing $40,000 from a bank in
Ottumwa, Iowa. The next year, with Bailey, Kelly, Frank "Jelly" Nash and
several others, he robbed a bank in Sherman, Texas of $40,000 on April 8,
1931. Reportedly, he was also involved in the killings of two Minneapolis
Police Officers December, 1932.
He then returned to mostly acting as a
hired gunman and was hired to free former partner Frank Nash from federal
custody. On the morning of June 17, 1933, Miller, along with Charles
"Pretty Boy" Floyd and Adam Richetti, attempted to free Nash while he was
being transported to Leavenworth Federal Prison. As Nash was being
escorted from the Union Train Station in Kansas City, the outlaws opened
fire in the escape attempt. In the end, Nash, along with four lawmen were
killed in what has become known as the
Kansas City Massacre.
Kansas City Massacre, Miller, accompanied by
girlfriend, Vivian Mathias, traveled to Chicago, arriving there about June 19, 1933. For a few days, he hid out with a member
of the Barker-Karpis gang. From there he then reportedly went to New York. On October 31, 1933,
an FBI investigation discovered he was back in Chicago with his
girlfriend. The next day, he escaped a trap set for him there by the FBI.
However, Mathias was taken into custody and later pleaded guilty to
charges of harboring and concealing a fugitive.
On November 29, 1933, as the FBI continued to search for Miller,
his mutilated body was found in a ditch on the outskirts of Detroit,
Michigan. He had been beaten and strangled. Information later received by the
FBI indicated that Miller had been involved in an altercation with a
henchman of Longie Zwillman, head of New Jersey's underworld mob, in
Newark. During the dispute, Miller shot the henchman and a short time
later another Zwillman associate reportedly retaliated by killing Miller.