A con man found guilty of defrauding a romantic partner of hundreds of thousands of dollars is set to argue the proceedings should be stayed because prison guards violated his rights with unnecessary and frequent strip searches.

In his application to Ontario’s Superior Court of Justice, Shaun Rootenberg argues the breach of his charter rights was significant enough to stop the case against him.

“Absent judicial condemnation, this systemic violation will only continue,” Rootenberg argues in his court filings. “(It) is a wide-scale and ongoing constitutional violation that the courts cannot condone.”

Police charged Rootenberg, of Thornhill, Ont., with fraud on June 6, 2017, saying he had used an internet dating site to lure victims. He was detained at Toronto South Detention Centre for seven months until winning bail.

“The applicant was subjected to hundreds of routine strip searches in humiliating and unlawful conditions,” his application states. “Strip searches were regularly conducted in the presence of other inmates and correctional officers, some of whom were female.”

The searches, Rootenberg asserts, were such an egregious violation of his rights that the extraordinary remedy of a stay is warranted — as other courts have at times concluded. He rejects Crown arguments that a sentence reduction could possibly be warranted, saying it wouldn’t remedy the situation.

In July, Superior Court Justice Beth Allen found Rootenberg guilty of defrauding Victoria Smith out of $595,000. The divorced mother of two had given him the money in 2013 to invest on her behalf. Instead, Allen found, he had used the funds to buy himself a new BMW and pay off gambling debts, among other things.

Last month, Allen refused to declare a mistrial amid his arguments that she was biased. However, she allowed him to mount his constitutional challenge, to be heard starting Wednesday.

Rootenberg, who was sentenced to three and a half years for fraud in 2005, also argues a stay is warranted because the prosecution failed to disclose materials in a timely fashion.

The current case also initially involved another of Rootenberg’s romantic partners, Dr. Kim Barker, the former medical officer of health for the Algoma Public Health Unit in Sault Ste. Marie, Ont., who knew him as Shaun Rothberg. The Crown did not proceed on those charges.

Barker has been fighting to keep secret an embarrassing report on her hiring Rootenberg in 2013 to be the health unit’s chief financial officer. The Supreme Court of Canada has yet to say if it will hear her bid to keep the report under wraps.

In his stay application, Rootenberg argues he was routinely strip-searched despite never having been accused of offences involving violence or drugs. The searches, he says, occurred both before and after court appearances, professional visits, and after finishing his shift on the work range.

He says other inmates, correctional staff including women, and even passersby could see prisoners being searched.

“Strip-searching inmates in this manner is degrading and humiliating, and only heightens the already mortifying experience,” he says.

Rootenberg was ordered released on bail in January 2018 but detained again for three months at the Toronto East Detention Centre, where he was again strip-searched.

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Courts have repeatedly stated the importance of ensuring such searches be carried out in maximum privacy. In addition, the Supreme Court has made it clear they are highly intrusive and humiliating, and need to be done carefully.

Strip searches in Ontario jails were subject to an independent review in 2017, which called their use “particularly troubling.” The Office of the Independent Police Review Director similarly identified widespread concerns.