A Conversation with Drake Bentley on Milwaukee, Media, and What’s Next

Award-winning investigative journalist Drake Bentley has joined the Milwaukee Courier and Civic Media team. Bentley has contributed to several local and national media outlets including the Milwaukee Journal Sentinel, Wisconsin State Journal, Newsweek, Heavy and The Sporting News.

Bentley will play an instrumental role in delivering the stories that matter the most. He’s a northside native who’s in tune with the community and concerns that impact Milwaukee residents. In a recent conversation I had the opportunity to speak with him about the stories that have shaped his career, what continues to drive his reporting, and what he hopes to explore next.

You recently joined the Milwaukee Courier, what’s the first story you’re looking to chase?

Before I left the Journal Sentinel, I was really interested in stories that people talk about but don’t fully know. One that stands out is Malcolm X’s time in Milwaukee as a young boy. There’s not a lot of detailed information about it, which makes sense because his father was involved in a lot of pro-Black organizations, and those records are hard to come by. That’s something I’d really like to dig into more just learning about the time the Little family spent in Milwaukee.

What’s your go-to food spot right now?

I’m a pretty easygoing food person, but my ideal meal kind of like a birthday meal I would probably go with Hup’s Pizza over on Hampton. Somewhere around 45th and Hampton, I think. I’d go with a supreme pizza, sausage, pepperoni, mushrooms, onions, and all the good stuff. You really can’t go wrong with that. It’s a place I grew up on, and I still enjoy it to this day.

What’s one story you’ve covered that stuck with you longer than expected?

There are a lot, but some of the ones that stick are the stories involving radio hosts, TV personalities, and meteorologists. When they switch stations or leave abruptly, it kind of sticks with you for a while.  Also, that overhanging Giannis story about the possibility of him leaving Milwaukee. Is he, is he not? Is he going to remain a Buck his whole career? The Giannis one has kind of stuck around.

If you weren’t a journalist, what would you be doing?

I actually decided to become a journalist a little later in life. I went to school for business, but I also have a strong interest in politics I was a political science major as well. So, I’d probably be working for a politician in some capacity.  Ideally, though, I like to think I could lead the Green Bay Packers to a Super Bowl as head coach but realistically, I’d be working in politics.

Where did you go to school?

I went to high school at Wauwatosa East; I was a Chapter 220 student busted in from the North Side. For college, I went to the University of Wisconsin–Whitewater for undergrad, and I earned my master’s degree from the University of Nebraska. I actually completed that entirely online during COVID-19 and never stepped foot on campus.

You’ve got one mic, one hour, and the whole city is listening to who’s your dream guest?

That’s a tough one. We’re fortunate in Milwaukee because a lot of big figures are actually accessible. But if I had to pick right now, I’d probably go with Jordan Love. Whether or not he’d divulge anything is another story.