Bob Willis: A life in corrections comes full circle
Growing up in Kingston’s Portsmouth Village, prisons were part of the landscape of Bob Willis’s childhood.
On his daily paper route, he could see the city’s psychiatric hospital looming in one direction, with Kingston Penitentiary (KP) and the Prison for Women in the other. In April 1971, he stood among the crowds watching the KP riot unfold as the military moved in.
Only five years later, he would begin his own career inside the federal correctional system. Over the decades that followed, Bob would work across institutions and parole offices in the Kingston area, build a close professional relationship with a young Anne Kelly long before she became Commissioner of the Correctional Service of Canada (CSC), and eventually watch his own daughter follow him into corrections.
Bob had not initially planned on joining CSC. At 16, he joined Kingston’s Prince of Wales Own Regiment and later became a psychiatric nursing assistant at the Kingston Psychiatric Hospital.
Then his wife, Nancy, who was working at CSC’s regional headquarters, came home one day and told him correctional officers were being hired.
“The pay scale was considerably more than what I was making,” Bob recalls. “I had a family and a mortgage. I was looking for secure employment that offered benefits and provided my family with a comfortable living.”
His military background and psychiatric nursing experience helped him through the interview. In December 1976, at 23, Bob arrived at Millhaven Institution.
Millhaven was going through considerable upheaval at the time, and Bob was struck by the violence.
“I was a small-town boy from Kingston,” he says. “The inmates would constantly say to me, ‘What do you know? You’re still a kid.’”
He remembers attending funerals for fellow officers and incidents that could turn dangerous in seconds. During one hostage taking, staff were trying to talk down an inmate holding a knife when the man suddenly turned it on himself. Experiences like that eventually led him into suicide-prevention training and hostage negotiation.
“You were constantly on edge because you could get called upon at any time,” he says.
Looking back over more than three decades in corrections, Bob measures the years by what was happening outside the prison walls.
He was working in a tower when news broke that Elvis Presley had died. He was in charge at Bath Institution on a night shift when inmates watching television learned John Lennon had been shot. At Collins Bay, a secretary came running through the office announcing that the space shuttle Challenger had exploded.
Years later, while working as a parole officer, he and his colleagues paused to watch the verdict in the O.J. Simpson trial.
“Some of the most important moments in history happened while I was working in corrections,” Bob says. “That just stands out.”
What stands out just as strongly are the people he met among the way - colleagues who became lifelong friends, with whom he golfs and meets regularly for movie nights decades later.
“All our closest friends are CSC retirees,” he says.
Collins Bay was also where Bob first worked with Anne Kelly, then a case management officer.
Their paths crossed again when Bob became a regional trainer and coordinator for CSC’s reintegration case management model. Anne coordinated the initiative nationally, while Bob worked closely with staff across Ontario.
When Anne retired as Commissioner in 2026, she wrote to Bob’s daughter about her father’s influence.
“I would not have made it to the position of Commissioner without his mentorship,” she wrote. “He ensured I was supported, challenged, and encouraged to grow.”
Bob’s own career increasingly moved toward parole, case management and reintegration.
In the 1980s, he appeared in John Kastner’s Emmy Award-winning documentary, The Lifer and the Lady, discussing why preparing offenders for release mattered.
“Like it or not, lifers are going to get out and walk the streets again,” Bob says. “That’s why, when they come into prison, we do our best to make them ready for the community again through treatment programs.”
But reintegration also meant confronting cases where the risks were very real.
While working as a detention specialist, Bob was visited by provincial police officers concerned about an offender approaching the end of his sentence. They were worried about Bob’s safety.
Bob showed the man’s photograph to his family and warned them to stay away if they ever saw him.
Not long after his release, Nancy encountered him herself.
She was stopped in her car at a red light as the man crossed the street and looked directly at her.
“She said, ‘I just about fainted. I realized, oh my God, it’s him,’” Bob recalls.
About a week later, Bob says, the man attacked a nurse in a hospital parking lot, slitting her throat with a knife. She survived only because medical help was so close.
“We had the odd occasion where I would have to say to my kids, ‘Be careful,’” Bob says.
Most of the time, he tried to keep the work away from home. “But they could feel some days there was tension,” he says. “I came home from my job as a guard and wanted to be quietly left alone. I had a few of those days when the job became overwhelming.”
Nancy understood that world better than most. She spent much of her own career within the federal public safety system, including at the National Parole Board.
For roughly 20 years, her career overlapped with Bob. They even trained parole officers together, Nancy explaining the Parole Board perspective and Bob covering the parole officer’s role - and they called it the “Bob and Nancy show.”
“We were able to complement one another and have healthy discussions,” Bob says.
Then, in 2023, came a moment he never imagined when he first entered Millhaven at 23.
When his daughter, Melissa, graduated as a correctional officer, Bob was invited to present her badge in the same staff college gym where he had graduated nearly 47 years earlier.
“The fact that I was able to hand our own daughter her correctional officer badge was an honour,” he says. “Melissa has made us very proud.”
Today, she is a CX-02 correctional officer and a member of CSC’s Guard of Honour.
Bob retired in 2008, but he and Nancy never stopped moving. They became tour directors, travelling extensively and leading groups to New York, Boston, Nashville and beyond. Today, they live on the Lake Ontario waterfront in Bath, close to their daughter and grandchildren.
Bob also found another outlet for the investigative instinct that once drove him to dig deeper into parole files: genealogy.
“It’s so much like my old parole officer job,” he says. “I liked to dig to find facts and figures so that my reports for the Parole Board were informative and not a carbon-copy assessment.”
His research has uncovered long-lost relatives, century-old photographs and the story of his grandfather, one of thousands of orphaned children sent to Canada from England in the late 19th century. He has also traced Nancy’s family history, including a connection to a relative who played for the Montreal Canadiens and won five Stanley Cups.
His research also unexpectedly put Bob and Nancy in front of the camera together. After ancestry.com reached out looking for members with interesting family stories, the couple travelled to Toronto to film a series of commercials for the company.
Bob has spent much of his life looking closely at people, first across a correctional system, and now across generations of his own family.
Perhaps that is why, after all the places he worked and all the history he witnessed, his measure of a life well lived is remarkably simple.
“I’ve been lucky in life,” he says.
More than anything, that is how he chooses to remember it.
