From John Howard CEO to jail: Peel fraudster gets a year behind bars

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A judge has sentenced a former chief executive officer for the John Howard Society of Peel for defrauding the organization that’s meant to help former criminals of $327,045 over seven years.

Darren Pennock pleaded guilty in the Ontario Court of Justice last year to fraud, breach of trust and six counts of uttering a forged document. He was sentenced to 12 months in jail and three years of probation.

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“Mr. Pennock stole money out of greed,” Justice Sandra Caponecchia said in her reason for sentencing dated Jan. 8.

“He used the funds to pay his personal (expenses), including but not limited to his legal fees, a storage facility, cell phone and dining out. He used it to support his lifestyle not withstanding he was being paid a good living wage, $125,000/yr.”

The Crown said Pennock should get two years less a day in jail, followed by three years of probation.

Pennock’s lawyer argued for a conditional sentence to be served in the community.

Pennock worked for the John Howard Society of Peel as their CEO starting in November 2012.

“He oversaw an annual budget of three million dollars,” said the judge.

“In August 2019 it was discovered that Mr. Pennock’s work credit card had a very high balance. The organization commenced an investigation into the defendant’s expense claims and discovered irregularities. Mr. Pennock’s employment was terminated in September 2019. Professionals were hired to conduct a forensic analysis and the loss was discovered.”

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Police charged him in October 2021.

The fraud included $40,895 Pennock spent on gift cards; $159,375 he shelled out on travel, meals and entertainment; $63,859 on tangible expenses/assets; $35,438 on legal fees; $23,076 on a vacation pay claim; $1,466 on storage fees; $812 on an iPhone; $764 on a Rogers invoice; and $950 in retirement gift cards.

“The investigation also revealed that Mr. Pennock forged the signature of a member of the board of directors on six different occasions between December 7, 2015, and December 2, 2017,” said the judge’s decision.

Pennock, 53, was raised in Mississauga.

“Mr. Pennock describes his father as hardworking and his upbringing as fantastic. His childhood included cottage time in the summer, time spent together as a family and more than one trip to Florida,” Caponecchia said.

“Mr. Pennock’s parents separated when he was either 10 or 12, after his father’s business failed. After his parents separated, he moved with his mother and sister to a smaller home, and they lived a more modest life.”

Pennock became a pilot after he graduated from high school. He worked in the field for a few years, then started a related business, which he sold to his partner in 2007.

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He worked as an air traffic controller from 2008 until 2012, before he was hired by the John Howard Society.

Now unemployed, Pennock spends three to four hours each Saturday volunteering with his wife at a cat rescue centre.

He divorced the mother of his two adult children in 2014 and married a former high school friend in 2021. “He resides with his second wife in a home they jointly own. His wife works.”

Pennock’s current wife, mother, children and sister “all have positive things to say about him,” said the judge. “His family members and longtime friend were all shocked to learn of the offences before the court. They all know him as a supportive father, son and partner.”

Pennock has twice battled cancer. “He is currently in remission and continues to experience some residual effects from his last treatment, including pain in his spine and problems with sleeping.”

Pennock told the author of his pre-sentence report “that when he committed the offences between 2012–2019 he was in a ‘dark’ place emotionally due to his health issues. He attributed his crimes to stupidity, lack of judgment and a sense that the ‘clock was ticking on his life span.’”

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The judge considered Pennock’s guilty plea a mitigating factor in his case. “I accept that his guilty plea reflects his remorse and regret. He also wrote a letter of apology to the John Howard Society.”

Pennock also made restitution to the John Howard Society after his fraud was discovered.

“To do so, he took out a second mortgage on the house he jointly owns with his current wife,” Caponecchia said.

“His wife now shares the liability that he incurred. The restitution was finalized on May 24, 2024, a week after his guilty plea, a year after a civil default judgment was made against him and his wife on May 11, 2023.”

Due to the passage of time, the judge gave “little to no weight” to Pennock’s 1990 conviction for possession of a credit card obtained by crime.

But Caponecchia stressed that his “actions were not isolated in nature. They took place over multiple years and involved repeated deceitful conduct.”

Pennock didn’t stop his fraud voluntarily, said the judge. “He ceased committing the offences because his employment was terminated.”

His actions weren’t impulsive, Caponecchia said. “His actions were calculated and required a concerted effort of manipulation of his co-workers and paperwork to conceal his conduct from his colleagues and the board of directors.”

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His crimes “involve a serious breach of trust,” said the judge.

“His employer, the John Howard Associate of Peel, is a non-profit charitable organization. The organization serves the most vulnerable and under privileged members of the community,” Caponecchia said. “It does not have deep pockets. Mr. Pennock knew the organization depends on donations, volunteers and staff who were paid a modest income, unlike Mr. Pennock.”

His victims include people who benefit from the services the John Howard Society provides, said the judge. “Every dollar Mr. Pennock stole over the years was money that he took away from the most in need: the underhoused, persons suffering from addiction, the mentally ill, and individuals who are food insecure.”

Current John Howard Society CEO, Kara Hart, told the court “programming suffered during the time Mr. Pennock misappropriated funds.”

Hart said she “continues to work to build back trust with members of the community on whom the organization relies. Funders no longer consider the organization a safe place to donate funds.”

Pennock’s crimes also caused the society’s “modestly paid staff members” to suffer, said the judge. “Mr. Pennock’s actions planted seeds of distrust amongst the leadership team. Feelings of anger, betrayal and shame linger to this day.”

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Donna Murray, who recently retired from the organization after 38 years, testified she had been responsible for overseeing the finances for the Peel chapter. “She feels Mr. Pennock took advantage of her trusting nature. She described how the defendant lied and deceived her repeatedly when she went to him to discuss financial irregularities. He made her feel stupid and gullible.”

Kathryn Lynch, a donor to the society and a former employee of the organization, told the court that she “feels shame for having played a part in Mr. Pennock joining the organization in 2012. She continues to blame herself for ignoring various red flags over the years.”

Lynch testified that she feels Pennock took advantage of her trust repeatedly. “Upon her retirement after 35 years of service, she was given a gift certificate. When she went to use it, she discovered it had no value. She later learned that Mr. Pennock used the gift certificate for himself.”

The judge was satisfied Pennock should not get a conditional sentence.

“Mr. Pennock’s moral blameworthiness is high, and his offences are grave,” Caponecchia said. “He used his position of trust as CEO to defraud a significant amount of money from a charitable organization that serves the most disadvantaged members of society.”

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While Pennock “returned the funds he misappropriated five years after he was terminated, four years after he was charged and a year after a civil judgment placed restrictions on the home he owns with his wife, the impact of his offences extends well beyond the money he stole,” said the judge. “The rippling effects of his acts persist to this day.”

Jail time “is called for to meet the principles of general deterrence, denunciation and to hold him accountable for the harm he caused,” Caponecchia said.

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