Man who chatted with teen about masturbation rerouted to jail

A man given a conditional sentence after he was convicted of child luring over discussions about masturbation with his boss’s 15-year-old son will have to serve part of his time behind bars.

Douglas Wayne Dew, 48, was convicted last August of one count of child luring after a trial before provincial court Judge Cynthia Devine.

Dew was charged after a series of late night instant messages on Snapchat between him and the boy, whom he worked with at a landscaping company owned by the victim’s father between between Aug. 12 and 26, 2020.

Devine said the communications, while not explicit, clearly inferred that Dew was luring the boy to invite sexual touching, namely to masturbate. She said Dew, an alcoholic, sent the messages while drunk late at night.

The judge gave Dew a one-year conditional sentence order — which amounted to strict house arrest — after his defence lawyers filed notice questioning whether the mandatory minimum for the crime, a year in jail, was unconstitutional. He was also given two years of supervised probation.

The Manitoba Court of Appeal ruled Dew must serve a 16-month jail sentence, less time served on the conditional sentence, in a May 31 decision written by Justice James Edmond. Dew is expected to serve about seven months in jail.

The decision, recently made public, was also signed by Justices Diana Cameron and Anne Turner.

“In our view, imposing a (conditional sentence) in this case is inconsistent with the fundamental purpose and principles of sentencing,” the decision reads.

The panel of judges denied Dew’s request to have the balance of the sentence stayed.

Devine ultimately decided that a fit sentence would either be less jail time than the mandatory minimum or a conditional sentence. She further found that the mandatory sentence was unconstitutional.

Crown prosecutors, who had sought three years in jail for Dew, disagreed with Devine’s ruling and filed an appeal, arguing the judge made errors in assessing how grave the offence was and how much moral blame could be given to Dew.

Prosecutors also said the conditional sentence was “demonstrably unfit,” the appeal court decision said.

The Court of Appeal ultimately agreed, ruling Devine made material errors in imposing the conditional sentence, which was set to expire in August this year.

The higher court said the trial judge minimized the harm done by the offence as well as minimized the conduct itself in the language she used in her written ruling.

“She stated that the messages ‘read like flirting,’” which the appeal judges said contravened a Supreme Court warning that the courts should avoid language that obscures trauma. That warning was made in a November 2023 ruling, which came after and was unrelated to Dew’s conviction.

The trial judge also underemphasized the aggravating circumstances at play in the case and overemphasized Dew’s personal circumstances, the appeal court said.

Dew struggled with his bisexuality in a rural community, described as homophobic, court heard. He was a longtime friend of the boy’s family and mentored the victim in mechanics, putting him in a position of trust.

In the appeal court’s view, the aggravating factors included Dew abusing his position of trust to groom the boy, his “persistent and unrelenting” messages over a two-week period, the manipulation in the messages, the way he exploited their work relationship to gain trust, and the wide gap in age between the victim and Dew, who was 44 at the time.

“We are satisfied that the principle of proportionality calls for a sentence to be served in custody in order to reflect the gravity of the offence and the moral culpability of the accused,” said the appeal court.

erik.pindera@freepress.mb.ca

Erik Pindera

Erik Pindera
Reporter

Erik Pindera is a reporter for the Free Press, mostly focusing on crime and justice. The born-and-bred Winnipegger attended Red River College Polytechnic, wrote for the community newspaper in Kenora, Ont. and reported on television and radio in Winnipeg before joining the Free Press in 2020.  Read more about Erik.

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