Bob Flynn smiles behind the mic at the WCSR station. Lauren Scott | Collegian

The voice of Hillsdale will go silent tomorrow, at least on the airwaves, when Bob Flynn of WCSR retires after 46 years. 

“It’s been a wonderful ride,” Flynn said. “I have enjoyed every minute of it.”

Flynn started working part time at WCSR the summer after his sophomore year at Hillsdale High School, which was in 1978. He started working full time in 1986.

Flynn said his father, Dale Flynn, worked at WCSR in the 1950s.

“I would tag along with him and come down and watch him be on the radio and he’d let me do little things like find records for him, gather some of the news for him, things like that,” he said. “And I thought, ‘Well, this is cool. He gets paid for talking. I could do that.’”

Flynn covers the news and announces birthdays on air, but he said he doesn’t have particular segments. 

“There’s no set structure to my program and I find that most fun,” he said.

Flynn said the best part of his job is that when he sits behind the microphone, he never knows what will happen. 

Aaron Petersen, Hillsdale College dean of men, said Flynn has been a blessing to Hillsdale.

“Bob truly has been the voice of Hillsdale,” Petersen said. “When I came back to work for the college, I would hear him on the radio during the week and at church doing the readings on the weekend.”

Flynn often reads during Mass at St. Anthony of Padua Catholic Church.

Flynn said he believes it is time to retire because of the direction WCSR and radio in general is headed. 

“We’re getting more into digital advertising,” he said. “We’re getting more into the social media aspect of things. And I understand, that’s the way the industry is going. I don’t want to go with it. You either adapt or die. I understand that completely.”

Flynn said it was a tough decision, as he loves the listeners.

“I’m going to be 62 in August,” he said. “I really don’t want to have to learn how to do it all over again, because the way I’ve done radio for the past 46 years is slowly fading away. It’s time for the younger people to come in and do it. It’s nothing about the people I work with. It’s nothing about the listeners, because I’m going to miss the listeners. That’s going to hurt the most.”

His wife, Cindy Flynn, said she has loved witnessing his commitment to the community of Hillsdale. 

“He was born and raised here in Hillsdale and he is a true Hillsdale person through and through,” she said. “He’d do anything for anybody.”

McKibbon Media Group hosted a retirement party for Flynn at Johnny T’s Bistro on March 21, and Cindy Flynn estimated 400 to 500 people attended the event. 

“He loves the town. He loves the community. He loves the people,” she said. 

Bob Flynn said his replacement will be Harrison James, who currently does the WCSR midday shows. He will take on Flynn’s air time, which is 2-6 p.m. 

James said he was at first intimidated by the idea of taking Flynn’s spot as afternoon host, but he is feeling better about it now.

“Now that I’ve filled in for him while he’s been on vacation, it’s been slightly less stressful,” he said. 

Flynn said he has experienced much kindness from the Hillsdale community since announcing his retirement. 

“A typical response I’ve been getting is ‘WCSR won’t be the same without you,’” he said. “That’s very sweet of them to say.” 

Mike Flynn, Bob Flynn’s former boss of 25 years who is not related to him, said listeners appreciate how open Flynn is on air.

“He is spontaneous,” he said. “He’s a people person. His life is an open book, even on radio. He’s a great employee, loyal to core.”

Mike Flynn said he’s gotten to know Bob Flynn quite well over the years, as they traveled and worked together. Mike Flynn ran the station after his father, former WCSR owner Tony Flynn, retired. 

“We had some disagreements over things, but nothing major,” he said. “In fact, he’s one of my favorite people. The radio station won’t be the same without him. I don’t know what they’re gonna do without him.”

Scot Bertram, general manager of WRFH Radio Free Hillsdale 101.7 FM, said the bond between the host and listeners is intense. 

“Bob has been welcomed into the homes of countless area residents, providing local news and weather, broadcasting high school and Hillsdale sports, and soundtracking the lives of thousands,” he said. “Bob will be deeply missed on the airwaves by many, which speaks to the power of local radio.”

Flynn said although he performs varying tasks at the station, his main job is to make people smile. 

“My job is to make somebody smile today,” he said. “If I have not made somebody smile today, I’m not doing my job.”

Flynn said over the years he has been a companion to many widows and widowers as they listen to him on air throughout the afternoon. He has been a companion to animals too. 

“I have learned that music makes cows happy and happy cows give more milk,” he said. “I was told by several farmers, ‘Oh Bob, we have you on all day out in the barn. Because the cows love you and they give more milk.’”

Petersen said he appreciates Flynn’s good wit and music taste. 

“What I liked most about him on the radio is his sincerity and how he spoke to all of us as if we were all his friends and extended family,” he said. “He has been a true blessing to our community.” 

Former Hillsdale College football coach Keith Otterbein said it was always great working with Flynn. 

“He was upbeat and positive about our players and teams, definitely a glass-half-full person,” he said. “Bob is a fixture in the Hillsdale community, his involvement with Charger athletics will be missed.”

Flynn said he has had some emotional experiences while working at WCSR, such as when his former boss, Tony Flynn, died. 

“He was 92 when he passed away,” he said. “But when he passed away, that was a tough day. Then they asked me to speak at his funeral. That was even tougher.”

Flynn said he also grieved when his former boss and WCSR owner Jamie McKibbon died in a boating accident in 2020. 

“It was tragic,” he said.

McKibbon’s wife, Katina McKibbon, still owns the station, according to Flynn. 

“We’ve had a couple other people that I worked with for a long time who have passed away,” he said. “It’s always tough because these people are my second family. It’s not just the people I work with.” 

Gary Wolfram, city councilman and professor of political economy, said Flynn’s voice will be missed. 

“Bob Flynn has been the voice of Hillsdale for decades,” he said. “He knows our community better than anyone I have met in the almost four decades my wife and I have been here.”

Flynn said he never pursued a radio career for money.  

“I don’t do it for the money. And I don’t do it for the glory. There is no real glory,” he said. “I do it because I make people happy. It’s nice to have somebody come up to me at the grocery store, or after church, or just out in the street saying, ‘You know, that thing you said yesterday just made me laugh.’ Then I’m doing my job.”