Their main criminal activities included voter intimidation, armed robbery, assault, illegal lottery, and murder.
Crippled by arrests and murders, the Bottoms Gang had ceased to exist by the time America entered World War I.
One of the most powerful was headed by John "Bad Jack" Williams, a former detective turned gangster who acted as an underworld liaison for Democratic political boss "Colonel" Ed Butler.
By 1904, Missouri attorney general and future governor Joseph Folk had smashed the Butler Machine and with it the Williams Gang.
One of the only survivors of Bad Jack's Williams' inner circle was 25-year-old Frank Hussey, a rarity as one of the city's only gangsters to have attended college; he majored in political science and business at St. Louis University.
During one 1906 speech at the House of Delegates, Hussey approached brewing magnate August Busch in order to convince him to stop holding up the passage of a bill.
Daley's operation was headquartered at the Hibernia Literary and Social Club at 2320 Olive Street, which also served as a hangout for the Bottoms gang members.
The Bottoms Gang marched into the Fifteenth Ward and openly confronted the Rats during the Democratic primary day of October 6, 1906.
While Frank Hussey hated the Egan Gang, Tony Foley was waging war against the St. Louis Police Department.
He and his friends had grown up mistrusting the police, and Foley's hatred for them tripled after his kid brother Tim was shot dead while burglarizing a newsstand in December 1906.
[3] By the beginning of 1907, Tom Egan began using his contacts within the police force to turn up the heat on the rival Bottoms Gang.
On the night of January 15, 1907, members of both gangs met in a peace conference at the Jolly Five Club, located at 1505 Morgan Street.
Several weeks later on March 2, after police pressure from the Gagel murder and Stapleton assault died down, the Bottoms Gang met at 20 North Eleventh Street to draw up a new political club charter.
One such incident, in the early morning hours of August 2, 1907, resulted in a running gun battle across the Bad Lands between the gangsters and the police.
At 9 o'clock, the Bottoms gangsters pulled up to St. Louis City Hall's Market Street entrance in an expensive coach.
[4] Due to police pressure, they had relocated their headquarters to a converted church now named the West End Athletic Club at Twenty-Second and Washington streets.
Patrolman John Hutton had told them several times to keep the noise down, which led to a confrontation where several members of the gang attempted to waylay and shoot him.
The two main leaders of this group, Edward Devine and Charles von der Ahe, were murdered by Egan gunmen in the fall of 1911.
A bartender and sneak thief named Henry Zang insisted on testifying against Simons, despite a slew of threats against his life.
The day of Red Simons's trial, March 2, 1914, the gang boss was accorded a special detail of detectives to protect him at the Municipal Courts Building (there had been a recent rash of gang-related murders at St. Louis courthouses).
With the help of Bottoms gangster Dave Creely, Dunn succeeded in killing one of the triggermen, Frank "Gutter" Newman, on June 8, 1917.
A handful of the surviving members had relocated to the Soulard district where they fell in with a local mob known as the Chouteau Avenue Gang.