Bob Flynn won the Nov. 3 mayoral election with 66.92% percent of the vote, according to the county’s last unofficial results as of press time.
“I’m very happy that the voters chose me,” Flynn told the Collegian. “I think that people were looking for someone who could bring everyone together to find a comprehensive solution to the issues they see here in the city. So now that’s what we’re gonna try and do.”
Flynn’s opponent, fellow councilman Matthew Bentley, won 33.08% of the vote, with 790 ballots cast for him, according to the unofficial results.
“I’ve been a listener for a long time, so I listen to people,” Flynn said. “I like to consider myself a good listener who can take into consideration all sides of a topic or situation, and then just try to work together to come up with the best solution.”
Flynn, who served as a city councilman for two years after retiring from being “the voice of Hillsdale” on WCSR 92.1 in 2024, said he looks forward to “hitting the ground running” when he is sworn in on Dec. 1.
“The two issues that are going to be on the top of the list are still working on getting streets going, and then in the next year or two, hiring a new city manager,” Flynn said. “That’s what I’m going to focus on.”
Flynn entered politics two years ago, running for city council in 2024. Flynn said that, while he believes his longtime presence in the community helped him win, he hopes his time on the council has shown Hillsdale he is ready to lead the city for everyone.
“I am going to be mayor of the entire city,” Flynn said. “The mayor represents everybody in the city: those that like him, those that don’t like him.”
Flynn also congratulated the new council members elected on Tuesday, and said he was looking forward to working with them.
“The new council members that were elected yesterday have been proactive over the last several months, so they kind of know what the issues are going into December,” Flynn said.
Bentley said that he was sure that Flynn will do a good job in the role of mayor.
“I called Bob at 11:00 last night to congratulate him,” Bentley told the Collegian. “We hope to have coffee next week to discuss the many opportunities before us. I think it’s safe to say that the negativity discourse will begin to subside in December.”
Bentley added that he and Flynn were focused on the future of Hillsdale.
“I’m very happy to have a new council, and we’re all relieved that the election is over,” Bentley told the Collegian. “Bob ran an honorable campaign.”
Bentley pointed out the public debate between him and Flynn, which was hosted by Hillsdale Conservatives, as one of the highlights of the race.
“I wish there had been more debates,” Bentely said. “I am very confident that mayor-elect Flynn will be a great mayor of council for Hillsdale.”
Hillsdale’s current mayor, Scott Sessions, congratulated Flynn on his win.
“The job of mayor is always challenging,” Sessions told the Collegian on Nov 4. “You are always trying to do what is best for the residents, and Bob will do just that. I wish him the very best.”
Sessions, who served as mayor from 2013-2017 and again in 2025 after winning a special election, reflected on his recent time in office.
“I made it a priority to restore stability within the city staff and establish a more productive work environment, putting an end to the toxic workplace culture that had developed,” Sessions said. “We also had great economic development. Since then we’ve had Marshalls and Culver’s come to Hillsdale, so I really believe the city is going in the right direction.”
Sessions added that he was proud of the road work his council was able to accomplish, even as the issue persists.
Sessions said he looks forward to keeping the day-to-day operations of the city running until Flynn takes over.
“The city’s moving in the right direction,” Sessions said. “It’s going to be great.”
