Recently, I did something I never imagined I would do. No, not jump out of a perfectly good airplane for no good reason.

I got in a car with a former mob guy — in downtown Chicago!

I admit I did hesitate when I realized what I was doing. It was not my idea. My boyfriend enjoys watching crime shows and is a bit of a movie buff. I am probably one of a handful of people who have never watched "The Godfather" or any of the other popular mob-themed movies.

We were enjoying a weekend getaway and had done the more traditional hop-on, hop-off bus tour and the river architectural tour, both of which I enjoyed.

As we were trying to come up with an idea, he discovered a “Family Secrets Tour” crime tour in downtown Chicago, where we were staying.

We read about the tour guide, Frank Calabrese Jr. My curiosity was piqued.

After finally finding a parking lot, we raced to the meeting spot. Frank Jr., wearing a black polo shirt, blue jeans and flip-flops, was leaning against a light pole waiting for us. I looked for the bus and didn't see it. Frank led us to a white four-door car and opened a back door.

The crime tour "Operation Family Secrets" begins as an explanation behind the tour by former mob member Frank Calabrese Jr. during a private tour around downtown Chicago. Jamie Lund
The crime tour "Operation Family Secrets" begins as an explanation behind the tour by former mob member Frank Calabrese Jr. during a private tour around downtown Chicago. Jamie Lund

For a split second, I wondered if I should run instead. I hesitated at the open door, wondering if getting into a vehicle with a former mob guy was really a good idea.

Then I decided it would be a great adventure and in I went. It was just the two of us on the tour and I sat behind Frank. As a photographer, it was driving me crazy not being able to take photos of him as he talked about his past involvement with the mob.

The tour was fascinating. Frank talks fast as he explains about his family life and how he entered the mob life. He discussed family dynamics and pointed out buildings as he told us why each was significant.

We drove through Chinatown. I was equally fascinated by the unique architecture of the buildings as we drove through as well as the first person account of the mob history.

I happily snapped photos of buildings from the back seat as Frank pointed them out.

The 59-year-old man explained when and why he decided he had had enough of the mob life and wanted to get out.

He had one huge obstacle blocking his path to freedom: his father. Frank and his father were sent to prison in the 1990s. Frank knew if they got out, one of them would probably die, and it would be him.

He contacted the FBI and offered to help them get his father. He did not want any compensation. He just wanted to live. Nobody knows how to push a parent's buttons better than their kids.

Apparently, mobsters are no exception. Frank was able to get the information that would eventually get his father locked up.

When Frank got out of prison, he moved out of the state. He moved back in 2018 and began offering tours.

Frank told us his father had never been called “Frankie Breeze." The media came up with that name.

The two-hour tour flew by.

When it was finished, my head was spinning as I processed the information. Both Frank and my boyfriend are about half-Italian, so it was no surprise to me that the conversation ended about a restaurant recommendation for lunch. It did not disappoint, either.

Jamie Lund is a reporter for the Pine Journal. Contact her at or 218-879-1950.

Jamie Lund
Jamie Lund