Part 110: Riley Shepard Speaks at the Memorial of Dr. Ben L. Reitman plus Grifter Influencers

Picture this: It’s 1942, Riley Shepard is twenty-four years old and living in Chicago. He looks like this:

This photo was included on flyers promoting his lectures in Chicago. My half-brother Richard and his wife gave the flyers to me in 2008, they were hidden in Richard's mother's attic. Riley presented himself as a pastor, one with a doctor of divinity degree. He was always coming up with new identities.

As a young man, much like young people now, Riley had his influencers. Today, we have instagram influencers. Years ago "Ted Talks" were popular. Back in Chicago from 1890 to1960, the "Bughouse Square Speakers" gave speeches on a variety of topics in a park located at 901 N. Clark Street. Riley would've seen a rotating cast of speakers with wacky names like "One Armed Charlie" Wendorf and Herbert "The Cosmic Kid" Shaw. More famous speakers over the years include Carl Sandburg, Clarence Darrow, Eugene Debs, and Studs Terkel. Did Riley speak in the park as well? That goes into the "I don't know" pile.

In his early years Riley met all kinds of people that shaped his views. He ends up speaking at a crowded memorial for Dr. Ben L. Reitman in Chicago at the LaSalle auditorium. Dr. Reitman was known as the physician to the poor, an advocate for hobos, drifters, and sex workers, but perhaps best known as one of the lovers of political activist and anarchist revolutionary Emma Goldman.

Did Riley meet Dr. Reitman because he needed free medical help, and they became friends?

Did they meet at political rallies?

My high school friend told me that he and my father had a conversation about anarchists back in the 80s, a talk which led my friend to believe Riley leaned that way. Riley leaned into various identities, and politically, like these other men, he leaned to the left, but I never heard him describe himself as an anarchist.

The more I read about the people in this newspaper article, below, the more I see my father’s early influencers. Chi-town in the 1940s...what a wild place it was.

Riley introduces himself at the memorial for Reitman as Richard Riley Shepard, pastor of the Liberal Church of Los Angeles, and a journalist quotes him in the newspaper clipping, below. The room is packed, over three-hundred people jammed in a small room, many total strangers to the doctor who’d died only a week prior. Dr. Reitman was a radical figure, his memorial drew in the curious, as well as a cast of Chicago characters.

Riley stood up and told of his first meeting with Dr. Reitman. “He was sitting drinking carrot juice and he looked like a bum to me. But I learned that he was a great man.”

After Riley, another speaker, Joseph “Yellow Kid” Weil, the best-known con man of his era, used the event to talk about his career as a grifter. Sounds like he went on stage to talk about himself instead of the deceased, we've all witnessed something like this, haven't we? "And another thing about me!"

Weil went on about how many people he’d swindled, how he only fleeced those that deserved it, like the rich and greedy. Lots of bragging from this one...but he did swindle millions. Weil lived to be 100 years old and couldn’t shut up about himself. There’s a book about him online at the Internet Archives site called “Yellow Kid” Weil: The Autobiography of America’s Master Swindler.” His elaborate schemes included fake locations, like the “big store” in the film “The Sting” starring Paul Newman and Robert Redford. Weil hired men to set up his cons, he set up betting rooms with full staff so the mark would think he was in a real place, instead of a set up. Riley may have picked up extra cash that way, plus some new tricks, I'm certain he admired Weil.

Weil’s line of thinking, that he only fleeced people who had it coming sounds familiar to me. Even the way my father described his childhood crime of breaking the windows of his grandmother’s grocery store––Riley said he did it to give food to the poor people in Wilmington. As a kid, I thought he was like Robin Hood, he did it to help people during the Great Depression.

Seeing this article explains a lot. These were the men Riley hung around in his younger days, he even wrote about meeting them in his journal. I wonder what they thought of him.

Special thanks to Russell Trivich for finding the article, above. In the photo in the upper right hand corner: Herbert "The Cosmic Kid" Shaw on the left, and Jack Sheridan, Hobo Poet Laureate–– men Riley mentions in his journal.