Montreal's naked gangster: Ziggy Wiseman insisted on full nudity at top secret meeting

 Richard Siegfried Wiseman, aka Ziggy Wiseman, met police Sgt. Michel  Lepine in a room at a South Shore motel in 1977 and he started stripping out of his clothing.
   Wiseman then nodded to Lepine to do the same.
   The two men, who had never yet met, were suddenly standing close to each other fully naked, with dongs, pecs and floppy bums fully exposed. 
   The naked Wiseman turned the television up loud and showed Lepine a gun, telling the cop that he'd be the first to die if police intervened in their meeting.
  Wiseman met Lepine to give him his first $5,000 weekly bribe to turn a blind eye to Wiseman's fast-growing whorehouses, which took the form of massage parlours and photo studios.
  Seeds of the relationship had been planted when Lucien Proulx,  chauffeur for later-disgraced mob lawyer Maurice Hebert, asked cop Lepine if he'd be interested in envelopes full of cash.
  Proulx gave Lepine $4,000 and a list of Wiseman's competitors.
  Before stripping down, Wiseman checked the hotel room for hidden microphones. He insisted on full nudity to ensure that Lepine wasn't wired.
   Wiseman had done his homework before undertaking his sex parlour operations. He had received the blessings of Joe DiMaulo, who was running the local mob while Vic Cotroni and Paolo Violi were in prison. Wiseman also received permission from the brutal Dubois gang.
   Lepine accepted the bribes only to make a case against Wiseman.
  Standing naked in his full glory, Wiseman had no clue that he was being set up to go down.
**
 Early the next morning at 7 am, 120 Montreal police officers raided Wiseman's 17 operations which promised in local newspapers "guaranteed total satisfaction for $35."
   Sex-seeking customers were permitted to pay with credit card and those unhappy with the sexual services were offered photos of a naked dancing girl, while others were chased out by a Doberman.
  Wiseman ran 20-25 such operations in Montreal, employing between 50-100 women - mainly aging strippers -  some of whom reportedly earned an impressive $75,000 a year. The sex workers received $7 of each $35 fee. A half dozen men managed the places and about 300 customers would drop in daily.
   A session involving oral sex and sexual intercourse cost $200, which represents a massive $990 in 2020 currency.
   Wiseman, who was tall and could be intimidating due to his boxing background, proved a lively witness when put on the stand to face over 40  morals and corruption charges in January 1977.
**
  Wiseman started out as a seemingly-respectable talent agent, managing the career of talents as singer Jenny Rock, who in 1967, at the age of 21, walked away from a busy pop music career to return to studies.
   Wiseman, who was calling himself Ziggy Richards at that point, told a reporter that he would probably move to the States to continue his craft now that his meal ticket had disappeared.
   Rock, in later interviews, said that Ziggy had been very kind and helpful to her throughout and their split was amicable, in spite of reports that suggested they were at odds.
  ***
  Wiseman watched the 1969 Woodstock Festival with great interest, vowing to duplicate the event in Quebec. He launched the Manseau Pop Music Festival for July 1970 but it turned into one of the great fiascos of the era.
   Wiseman borrowed money from gangsters Willie Obront and Frank Cotroni to hold the event in a rural town between Montreal and Quebec City. Acts were to include Dr. John, Johnny Winter and Little Richard, a lineup that the costly $15 ticket noted was "subject to change."
      Dr. John was the only one of the big names to actually perform and was reportedly never paid for their three hour show.
     Six hundred attendees required medical attention for LSD trauma while another 180 required medical attention for such issues as cuts and burns. Eighteen required ambulances.
  The Bourassa government opened an inquiry into the event and vowed never to let another such show happen again
**
   Wiseman then went into the gambling business, which led authorities to order him to testify at the crime commission of 1973.
  A refreshingly-candid Wiseman came clean with juicy stories, telling the commission that he ran a Bahamas-registered company Grand Cayman Amusements Ltd which ran free gambling junkets.
  One time an employee withheld profits. He only had $3,000 of the $16,000 he owed.
  Wiseman and pals interrogated the man in the Holiday Inn on Cote de Liesse.
  "He was a little bit terrified so he jumped out a second storey window. He claimed he was injured but nothing serious."
   Wiseman said he'd make about $10,000 on such junkets but about half would be spent on office expenses which included a $2,000 monthly phone bill. He ran four such junkets over nine months.
   The trips were free but those who didn't gamble were sent home or charged for the trips.
   "I sent 26 people home one time. They were playing golf all day and at night they were too tired to go to the casino."
   Wiseman said he had several Monteralers recruiting potential gamblers: Charles Bouchard, David Shusters, Sam Lowsky, Johnny Malo, Marcel Martel and Frank Walkovitch.
   He told the commission that underworld creditors give gambling debtors four years to pay.
  "Not that they don't have muscle. But if a man has no money, violence cannot make him pay."
    He told the hearings of a time when he intimidated a man who owed him money.
   "I shook him up a little. I'll say I gave him a love tap. That's not violent. I slapped him in the mouth. I figure when I hit a guy, if he's still standing up then I didn't hit him."
   The debtor paid off his $1,500 debt with one hour.
   Wiseman said he had to stop the gambling trips when lucky gamblers won $178,000 at his tables.

***
   Wiseman also had a hand in a fraudulent coupon operation known as "Bottin vert" which also led him into some hot water.
   Allen Dawson and John R. Ferguson called cops on Wiseman and had him prosecuted for $75,000 fraud after they bought shares in a company he owned that they later learned had no value.
   The duo was unaware that Wiseman's company had only $100 in its account in a bank in Ste. Anne de Bellevue.
    The company Bottin Vert, aka Green Book, gave retail discounts to people who bought the book of coupons.
  The case went to court on 27 October 1976 and Wiseman dodged a bullet, as Justice Emile Trottier acquitted him of all charges.
***
    Wiseman's end was near when he was sentenced for 54 months in prison in August 1977 for prostitution ring, which could have potentially earned up to $8 million a year.
   Some believe that he would have faced a lengthier sentence had he not previously come clean at the crime commission.
  Wiseman had a bum ticker and was a frequent visitor to the Royal Victor Hospital for heart issues. His lawyer Frank Shoofey accused authorities of triggering a heart attack by keeping him in leg shackles.
  He died of a drug-induced suicide while at home on convalescent leave.
  He wrote a two page suicide note to his wife and two kids before killing himself with drugs on weekend leave at his home in mid-Dec. 1978. He was slated for parole two months later.
   He had previously promised that in the event of his early death, documents would be handed over to police with evidence against his rivals.
    About 30 attended his funeral.