Category Archives: Stories of Five Dollars and Other Amounts of Money

Stories of Five Dollars and Other Amounts of Money
This is a series of first-person told stories about what money means to us and the part it plays in our lives. It’s about how far people will go to get money; and how money can really mess things up – whether your pockets are empty or overstuffed. I produced these stories together with writer Alex Kotlowitz – the author of “There Are No Children Here,” among others. Together we conducted the interviews; I edited and mixed the audio. These stories originally aired as part Chicago Public Radio’s series “Chicago Matters: Money Talks,” funded by the Chicago Community Trust. Versions of many of them also aired nationally and internationally on several programs, including “This American Life.” A few of them were even adapted for stage by the Chicago theater company Pegasus Players. Thanks to photographer Jason Reblando for the pictures.

Five Dollars

Sometimes a small amount of money can mean more than it should.

Addicted to cocaine and desperate for every dollar, Albert Ellis’ life was a mess. Then he got into an argument over five dollars.



Going Broke

Going broke is tough enough, and then friends – and even total strangers – want to tell you how run your life. That’s what happened to Meg T.

Meg T. graduated from law school, expecting to do fairly well in life. But she soon found herself thousands of dollars in debt – because of student loans, infrequent work and overspending. Meg eventually filed for bankruptcy. She knew there would be repercussions to her financial profile, but she didn’t anticipate the other effects.

The Conned Artist

Sometimes the lure of money can cloud your judgment.

Tony Fitzpatrick is a Chicago artist. He’s a big man in appearance and words, who likes to consider himself pretty street-smart and savvy– not someone easily tricked. Then he was offered a chance for the money and glamour of the big-time art world.

A version of this story also aired on This American Life as part of the show “Getting and Spending.”

The Trouble With Money

With wealth comes security, power, and sometimes, surprisingly, a lot of discomfort.

Rachel Durschlag, heir to the founder of Sara Lee, grew up with a lot of money. But rather than accepting her good fortune, she struggled with it from early on.

Dialing for Dollars

Sometimes money can get in the way of your best intentions.

Marty Oberman entered politics out of the 1960’s anti-war movement, filled with idealism. After serving as an alderman, he decided to run for higher office. But first he had to raise the money – lots of money.

A version of this story also aired on This American Life as part of the show, “Getting and Spending.”

Human Commodity

Money is a means of exchange used to acquire goods or even status. But what happens when a person becomes a form of wealth?

Fanny Clonch is now a high school teacher living in Chicago. But for a period of her childhood, after being orphaned in Morocco, she was trapped in households where she was nothing more than a commodity. The story of her grandmother, who as a child had been sold into slavery and eventually escaped, inspired Fanny to find a way out.


This story also aired on Radio Netherland Worldwide’s The State We’re In.

Rolls Royce Rings, Gold Teeth, And Other Financial Investments

Dan Lebo works in Chicago’s rough West side helping run the family business – a pawn shop.

From women seeking cash for their kids’ school supplies to sons pawning valuables stolen from fathers, day after day Lebo experiences a unique window into people’s lives – all over the exchange of money.

A version of this story aired on This American Life as part of the episode “Getting and Spending.”

All The Pigs In Denmark Will Be Dead

Money isn’t everything – except when you’re a trader in Chicago.

Ted Fishman was a trader for almost nine years back in the 1980s. He fell into it by accident, looking to try it out for awhile before applying to law school. He was quickly swept up in the adrenaline rush of streaming numbers, waving hands, and ruthless competition for every dollar. Soon Ted was making money hand over fist. But he was losing touch with his own best sentiments.


A version of this story aired on This American Life as part of the episode “Getting and Spending.”

Making Ends Meet

What happens when you’re unwilling to let go of a lifestyle you’re no longer able to afford?

Bill Thompson was a commodities trader raised on Chicago’s affluent North Shore. He was accustomed to a moneyed lifestyle, always getting everything he wanted. But after losing his job, things started unraveling. Bills couldn’t be paid, his already unhappy marriage got worse. He started looking for a way out.


A version of this story aired on This American Life as part of the episode “Getting and Spending.”