Berry was born in Peterborough into a Roman Catholic Irish family and had what was described as a "horrific upbringing" with both of his parents being severally verbally and physically abusive.
[4] Believing himself to be the hideous monster that his mother told him that he was, Berry was full of rage against the world and he took up boxing as his principle hobby as a teenager in the 1950s.
[4] As boxing and organized crime are closely linked in Canada, Berry's skills as a boxer soon led him into the outlaw biker clubs in the early 1960s.
[4] He attracted much attention with a street fight against George Clark of the Vagabonds biker gang that led to the police blocking off Avenue Road for an hour while taking bets about who would win.
[2] Berry was a founding member of Satan's Choice Motorcycle Club in 1965 and made his reputation with a celebrated street fight in Toronto against Howard "Baldy" Chard, the former boxing champion in Kingston Penitentiary and the principle enforcer for the gangster Johnny Papalia.
[6] Berry became the most infamous member of Satan's Choice, who purposefully lived a life of poor hygiene and who wore filthy clothing, hence the nickname Pigpen.
[6] His reputation was that of a wildman as Berry engaged in such disgusting antics such as vomiting over new members of Satan's Choice, eating live birds and mice, and attaching a dead skunk he found on the road to his biker's vest.
[11] The production of The Proud Rider was a troubled one as on the first day of shooting, 3 October 1970, the Toronto police arrested a Satan's Choice biker on the set.
[11] Berry who played himself in The Proud Rider was a disruptive presence on the set who refused to take direction and constantly engaged in bizarre antics designed to shock and appall the film crew and actors.
[15] Erslavas who went hunting with Berry in one of the vast forests that cover northern Ontario in winter of 1975 complained that Berry as an odd character who was frightened of owls and shot the wings off one of owl because he disapproved of the way that the owl looked at him..[16] Erslavas stated it was a major mistake to let Berry cook the food for the Thunder Bay chapter of Satan's Choice as he urinated in the brine he used to cook the partridges he had killed during the hunting trip[16] In 1974, the Montreal chapter of Satan's Choice became involved in a biker war with the Popeye Moto Club.
[24] Starting in the early 1970s, Satan's Choice members operated drug labs in cabins in northern Ontario, with production focusing especially on PCP and methamphetamines, better known in the area as "Canadian Blue".
[25] Under the terms of the alliance, the Outlaws served as the exclusive distributors in the United States of the PCPs and methamphetamine manufactured by Satan's Choice in northern Ontario.
[27] The drug network for selling the PCP went from northern Ontario down to Florida, and the police estimated Guindon just by himself was making at least $60 million per month in sales.
[28] Verg Erslavas, the president of the Satan's Choice Thunder Bay chapter stated: "After Howard went to the OLs [Outlaws] it opened the door for even more association/biz.
"[24] Berry was convicted in North Carolina for a series of auto thefts along with an attempt to steal a tank from a United States Army base.
[30] Berry was for a time said to have glued a plastic copy of a diamond to his forehead and wandered around Ontario pretending to be a swami (Hindu holy man).