Soon becoming successful distributors the gang, with partner Joseph Stenson, owned several breweries by the early 1920s using its wealth to gain political influence and police protection.
The gang was soon noticed by Al Capone, due in part to the scandal, and upon their release in 1925 following the bootleg wars an alliance was formed between the gang and the Chicago Outfit, agreeing to give Capone 40% of their earnings in exchange for protection from Ragen's Colts gangsters Danny Stanton, William "Gunner" McPadden, Hughey "Stubby" McGovern, Raymond Cassidy, and Frank "Dutch" Carpenter (although many of these men would be killed during the bootleg wars).
Serving as the Chicago crime syndicate's leading enforcers many of the gang members, including Terry Druggan, retired extremely wealthy.
Terry "Machine Gun" Druggan (1903 – March 4, 1954) was an Irish-American mobster and leader of the Chicago based Valley Gang from 1919 and through the prohibition era.
On one occasion, when he was disqualified at one track for fixing the race, Druggan pulled a gun on the officials and threatened to kill them all if they didn't change their ruling.