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Roy Norman Hennessy emanated an infectious love of radio throughout his long, distinguished career.Courtesy of the Family

In 1984, a young man was in the middle of a cross-country marathon in support of cancer research, heading into Winnipeg on willpower and an artificial leg. His plight caught the attention of Roy Hennessy, general manager of local radio station CKY-AM/CITI-FM, who found out the homesick 18-year-old runner, Steve Fonyo, missed his mother.

“Well, he won’t be missing her tomorrow,” Mr. Hennessy told his news director.

On Mr. Hennessy’s instructions, the news director, Charles Adler, rushed the young man’s mother on a plane from British Columbia so she could be at the radio station where her son would be interviewed live on-air in the morning. For Mr. Hennessy, the matter was personal: As a young adult he had learned he was adopted, but he had so far been unsuccessful in locating his biological mother. “It was a touchy subject with Roy,” Mr. Adler recently told The Globe and Mail.

The surprise reunion between the mother and son aired on the breakfast show. Mr. Hennessy, a showman at heart, had pulled off the heartwarming spectacle, but wasn’t present in the studio when it occurred. Mr. Adler headed to Mr. Hennessy’s office to report what had happened.

“Roy listened to every minute of it on the radio,” Mr. Adler recalled. “And when I found him he was sobbing.”

Roy Norman Hennessy, who emanated an infectious love of radio throughout his long, distinguished career as an on-air personality early in his career and an off-air manager and executive, died on June 7 in Mississauga of colon cancer. He was 80 years old.

The well-liked radio man was known as the “Real Roy Hennessy” during his star deejay stint at Vancouver’s CKLG in the evenings and morning drive time. From 1964 to 1976, he competed for ratings in his hometown market with Red Robinson, Jack Webster and other stalwarts of the era. He then transitioned to management roles with major radio stations across the country, and later co-owned an advertising and media consulting firm in Ontario.

At a time when radio jocks were rock stars, Mr. Hennessy was a finalist in The Most Handsome DJ in the World contest in 1968, run by Teen Life magazine. Qualifications included an “entertaining platter chatter,” as well as Mr. Hennessy’s six-foot height and brown hair and eyes.

What wasn’t mentioned was his hutzpah and a flair for the razzle dazzle. As general manager at Toronto’s CFRB-AM in the early 1990s, he not only invited then-prime minister Brian Mulroney to appear on the morning show, but had the audacity to ask the leader of the country to record some station identifications. Mr. Mulroney agreed to do the on-air promos.

In Winnipeg, he was denied a request to buy a giant motorhome for remote broadcasts. His superior told Mr. Hennessy he’d be fired if he purchased the vehicle. Undeterred, Mr. Hennessy traded airtime promotion (not cash) for the motorhome he dubbed Satellite One. He was not sacked.

Among friends and colleagues (if you were the latter you were likely the former as well), Mr. Hennessy’s “Real Roy” moniker extended beyond the radio booth. “It fit him perfectly,” said industry veteran Marty Forbes, retired president of Radiowise Inc. “He was the same real guy off the air as he was on the air.”

In management roles at stations in Edmonton, Calgary, Winnipeg, Toronto and Vancouver, in both talk radio and music formats, Mr. Hennessy established a reputation as a collegial boss, a dedicated socializer, a willing storyteller, a generous mentor and a leader who lived to create stars and give them full rein to flourish.

“I don’t think Roy ever critiqued my on-air performance one time,” said broadcaster Jody Vance, who worked for Mr. Hennessy at CHHR-FM (now CHLG-FM) in Vancouver. “He would often walk by and give me a smile and a thumbs-up through the control room window. I always thought he was my biggest fan.”

Mr. Hennessey and Brenda Liwiski, his longtime partner, who survives him.Courtesy of the Family

“He gave people opportunities,” said Ron Taylor, who worked with Mr. Hennessy in Winnipeg. “He allowed people to try jobs or change jobs who had no experience.”

Though his professional life was dedicated to an audio medium, Mr. Hennessy’s most beloved communications were transmitted by a look or a wink. “Roy would hold his savvy in the sparkle of his eye,” said Ms. Vance. “He would let you finish your thought at staff meetings, some of which were quite passionate.”

Mr. Adler, a prominent broadcaster and political commentator whose on-air career began with Mr. Hennessy in Calgary, remembered the same gleam. “I never met anyone whose twinkle in their eye could fill you with as much pride as he could. When the team did something really well and Roy’s eyes twinkled, that was a great day to be alive.”

Outside the radio station, Mr. Hennessy’s passions were family and a 40-foot boat called Liberty that was docked at Toronto Outer Harbour Marina. At the end of the season, Mr. Hennessy would hold an annual get-together with the other boat owners. The ritual involved tall drinks, long goodbyes and the all-day playing of Leonard Cohen’s Closing Time blasted from speakers.

Mr. Hennessy’s appreciation for that song was well known among the staff at CHHR. “Any time during my show when Closing Time came on, Roy would show up outside the control room and we would waltz in the hallway,” recalled Ms. Vance.

Mr. Hennessy was part of the ownership group that gained a license for CHHR, an adult-alternative album station branded as Shore 104 amid the recession of 2008. When the station launched, he served as president. The format ultimately did not succeed; it was his last executive position in radio.

As a young man in the 1960s, Mr. Hennessy had gotten into the radio business at a time of Beatlemania. His career spanned the transformation from family-owned local commercial stations to the more corporate, centralized and computerized medium it is today. In many ways, Shore 104 and Mr. Hennessy were throwbacks to the more communal terrestrial radio environments of the past. Hanging outside his office was a ship’s bell that was wrung to signal it was time for end-of-day beers and burgers on the patio.

“Roy was a pillar of those earlier times, and he would tell us stories,” said Ms. Vance. “We were staff who felt like we were family sitting around a very special table. Roy fostered a sense of family that I think is missing in media today.”

Mr. Hennessy was born Feb. 25, 1942. He was raised in Ladner, B.C., the only child of adoptive parents Jim Hennessy (who worked for the telephone company) and homemaker Lillian Hennessy.

Mr. Hennessy trained at the British Columbia Institute of Technology in the broadcast program in the early 1960s. The first song he played as a professional disc jockey, at CKOK-AM in Penticton, B.C., was the Chiffons’ One Fine Day in the summer of 1963.

Mr. Hennessey with his birth mother, June Lehman, who he reunited with late in life.Courtesy of the Family

In 1964, he took on an evening shift in the newsroom at CKLG-AM but was soon recruited to fill in as an evening deejay in an emergency to cover for a missing jock. “You’ve got a couple of hours to learn the board and check out the playlist,” program director Sam Holman told him. “Good luck.”

Mr. Hennessy passed the impromptu audition and worked his first news conference on Aug. 22, 1964. The Beatles were playing their inaugural Canadian concert, at Vancouver’s Empire Stadium. The media event took place underneath the stadium, just before the twisting, shouting and Love Me Do-ing was set to begin on stage. These were peculiar, ecstatic times in music radio: Tom Peacock of CFUN-AM shook hands with Beatles guitarist George Harrison, only to quickly wash his hands and later gave a vial of the water to a contest winter.

Mr. Hennessy himself did not figure prominently in the historic happening. “I didn’t get one question because Jack Webster wouldn’t shut up,” he later recalled, referring to the popular radio personality known informally as the “king of the Vancouver airwaves” while at CKNW-AM. “But leaving with McCartney’s autograph certainly upped my status in the family.”

Family was paramount to Mr. Hennessy. In 1973, at the age 31, he found out he was adopted. But the records were sealed – he never told his parents he was in on the family secret.

In 2016, Mr. Hennessy received an e-mail informing him that his birth mother had been found alive and well in Victoria. He was 74; she was 89. June Lehman grew up in the Fraser Valley and had given birth to her son at a Vancouver home for wayward girls. Mother and child were separated immediately.

Their reunion took place at the airport arrivals lounge in Victoria, with Mr. Hennessy carrying a sign that read, “I want my mother.” He had flown from Toronto – his new-found mother waited for him, tracking his progress across the country on her iPad.

“I walked up to her and said, ‘June, may I please call you Mom?’ Mr. Hennessy told the Vancouver Sun in 2017. “She was shaking.”

Discovering his mother’s identity was literally a lifesaver. Mr. Hennessy’s half-brother from Ms. Lehman’s side of the family would donate a kidney to Mr. Hennessy’s son, who suffered from a rare genetic disorder. The game-changing family events amazed Mr. Hennessy. “Sometimes in the middle of the night, I get up and just look out the window and shake my head,” he said. “It’s really surreal.”

Mr. Hennessy’s own health began to fail recently. He had dictated his own epitaph. A one-word obituary published after his death amounted to just one word: “Gone!”

A radio man needs a sign-off.

Mr. Hennessy leaves his partner of 37 years, Brenda Liwiski; and children Shannon Hennessy, Craig Hennessy, Candice Landry, Meaghan Hennessy, Alexander Hennessy and Patrick Hennessy.