It's hard to believe Bill Cunningham was once a Democrat who aspired to be elected judge in Hamilton County. 

He's long since become one of the Midwest's top conservative voices, closing in on 40 years of calling 'em like he sees 'em weekdays on 700 WLW. Cunningham's powerful mic has helped to thrust him into a new role in recent years – unofficial adviser to President Donald Trump. 

"He'll call me now and then and ask questions about what's happening," Cunningham told The Enquirer's weekly That's So Cincinnati podcast. "I give him my perspective on the Midwest. I tell him what I think he's doing right, what I think he's doing wrong. He wants to know how what he's doing is playing in Ohio. I give him my opinion and he likes it because I'm critical at times."

Also on That's So Cincinnati, Cunningham addressed his future; reflected on the day he was pressed into a career he never planned to have; and discussed his biggest regret in 38 years on the air. Here's more a sampling of the in-depth interview with Cunningham: 

Cunningham's contract is up in two years. 2022 will mark his 40th year on WLW. He said he's talked to recently retired Hall of Fame baseball broadcaster Marty Brennaman about the process of retirement, but Cunningham hasn't decided yet whether he'll call it a career in 2022.

Cunningham's wife, Penny, retired from Ohio's First District Court of Appeals last year.

"We're both in good health, thank God," said Cunningham, 72, who can be heard 9 a.m. to noon weekdays and 9 p.m. to midnight on Sunday. "Penny wants to travel. We have a nice place in Florida at a club. My friends are there. Penny's reforming the bylaws of the club. We want to spend time together." 

Cunningham added: "But right now, (radio) is what I want to do. Penny knows when I get up in the morning, I'm motivated to do it."

'I was unnecessarily cruel'

Asked who his favorite all-time local has been, Cunningham said former Cincinnati Mayor Charlie Luken. The question prompted Cunningham to reflect on the biggest regret of his radio career. 

It was in November 1993, after city of Cincinnati voters passed a charter amendment restricting certain legal rights for LGBT citizens. Roxanne Qualls was elected mayor that same election, and there were a lot of questions around town about her sexual preference.

Cunningham invited reporters to WLW's studios to talk about Qualls and the charter amendment. 

"With the media present, I asked if she is gay," Cunningham said on the podcast. "I shouldn't have done it. It was the biggest mistake and blunder that I made. It was a big news story at the time. But man, I thought about it. On a human level, I was unnecessarily cruel." 

Cunningham said he's seen Qualls one time since, sometime in the late 1990s. If he had the opportunity, Cunningham said, "I would apologize to her."