Richard Wolfe started carrying a handgun to school at the age of 13, and after his gun was discovered by a teacher, resulted in his first criminal conviction on 2 February 1989. By 1990, the Indian Posse moved into automobile theft and armed robbery. By 1991, the teenage Wolfe brothers had moved into drug dealing and prostitution and by 1992 had rented a house for $866 rent per month. In 1991, the Indian Posse had established an open air drug market outside of the Merchant's Hotel, known locally as "the Merch", on Selkirk Avenue in the North End of Winnipeg. The drug market outside of "the Merch" became one of the largest emporiums for buying drugs in Winnipeg. The Lord Selkirk Park Housing Development, whose inhabitants were almost entirely First Nations or Métis people, had become the stronghold of the Indian Posse, whose members sold cocaine, LSD, heroin, and marijuana. The Third World poverty of the North End of Winnipeg made joining the gang attractive to many young people. Richard Wolfe was considered to be the "diplomat" who was calm and able to think in the long term while Danny Wolfe was the "warrior" who was a hot-head who thought only in the short term. On 1 June 1993, the Indian Posse was mentioned for the first time by the Winnipeg Free Press, who described the Indian Posse as the gang that caused much crime in the North End.
