When Jimmy Freund’s cell phone rang on August 19, he didn’t want to answer. Freund, the managing director of Terrapin Theatre, was in a meeting with the director of the company’s next play, and he was pretty sure it was his girlfriend calling.

The medical examiner would rule Brad Winters’s death a homicide by stabbing, with strangulation a contributing factor. He was 38, a short, impish man with an alabaster complexion and strawberry blonde hair. He’d grown up on a dairy farm in Salesville, Ohio, but it was always obvious to his family that his heart was somewhere else. As a teenager he joined a drama program in Cambridge, a nearby town. “I realized he was good when he was in this play at Cambridge and he had to eat an apple,” says his mother, Lathiel. “He did it very well. He hated apples.”

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Terrapin had been founded in 1992 by Syracuse University graduates who migrated to Chicago to do theater. The company took its name from Terrapin Station, a Grateful Dead album.

Terrapin put on two plays a year on an annual budget that never exceeded $40,000. There was never enough money. In the spring of 2002 Winters directed Brimstone and Treacle, a dark family drama by his favorite playwright, Dennis Potter, who was famous for the Singing Detective TV series on the BBC. The actors didn’t get along, and, worse, no one came to see the play. “There were nights when we felt we were really entertaining the folks–all three of them,” cracks Sean Cooper, a cast member. Nearly broke at the end of the run, Terrapin axed its fall production.

Several Terrapin members questioned this shift. “I just thought, this puts a whole new perspective on things,” says Shimer, an early opponent. “So many companies want to go with the next big playwright. Steppenwolf does, and all of a sudden we’ll have to compete with them. Here’s poor old Terrapin, and we’re going to have do a lot of reading–and kiss a lot of frogs–till we find something that’s right.” But Winters was forceful, he was charming, and he could speak the daunting language he picked up at Kellogg. Eventually even Shimer surrendered to his point of view. The August 2002 vote to go forward with new plays was unanimous. (Pam Dickler, who missed the vote, would leave Terrapin partly over the new mission. “For me, this was too limiting,” she says.)

“He would voice his frustration about being unable to meet someone special,” says Sean Cooper, “and I would give him a pep talk. He was somebody who had insecurities about his lovability. I would tell him to get over it. ‘There’s somebody for everyone,’ I told him. But he never found that person, as far as I know.”

Winters left sometime after midnight and apparently alone, says Little Jim’s manager Jef Morgan. The occupant of the apartment next to Winters’s studio recalls hearing a noise sometime around 3 or 4 AM. “It was a kind of shout. I heard a person say ‘somebody,’ and maybe ‘help.’ I’m not sure. It lasted for two or three seconds. I thought it was coming from downstairs. In the back of your mind you think, ‘Oh my God, what is this?’ Then you dismiss it as a bunch of college kids walking by off Clark Street.” This neighbor, who asked not to be named, says he got up but heard nothing more–no creaking in the stairwell or any other sound–and eventually went back to sleep. The neighbor also says a woman in an apartment across the alley reported hearing a cry of “Help me!” come from Winters’s studio at around the same time. Police wouldn’t confirm or deny this.