BY PETER DORFMAN
The New York Life Insurance Company business card reads “Eric ‘Rachael Jones’ Wininger, Agent.” While the name on the card might bewilder some, for many Bloomingtonians there’s no mistaking the tall, striking, transgender woman presenting it. They know Rachael Jones as the former owner of Rachael’s Café, a popular East Third Street meeting place for eight years.
The café was an institution, with live entertainment, a flamboyant clientele, and unpredictable conversation. It was a fragile business, but a unique cultural phenomenon. It even inspired a play — Rachael’s Café — written by Indiana University graduate Lucy Danser and produced in London in 2014.
“Anyone was welcome, if they were kind,” says the 56-year-old Jones. “I wanted to bring all kinds of people together over a cup of coffee.”
In 2015, rising rent forced the café to close, thus beginning a year-long odyssey.
Like many transgender people, Jones felt remote from mainstream society. And she’d had a financial setback. “I’d literally put everything I had into the business,” she says.
Jones took a cross-country motorcycle trip to clear her mind and sort things out. Growing up in Bean Blossom, Indiana, in a conservative Mennonite family, she’d felt like an outsider, but biking across the south, she found that society had grown more open-minded. Returning to her home in Brown County, she worked as a waitress at Nashville’s Pine Room Tavern.
After a few months, she decided to hit the road again. “I had a homemade kettle corn maker, a snow cone machine, and an old motorhome, and I was going to travel from festival to festival,” she relates. “I did that regionally in Indiana, and it was a great experience.”
Then an acquaintance, a retired female New York Life agent, suggested there might be a place for Jones at the Fortune 100 insurer. Jones had sold insurance previously, but that was more than 30 years ago.
“She arranged an interview for me in the Carmel office,” Jones says. “It was surreal, walking into that big building in high heels. But they hired me. New York Life has a program to help LGBT people train to be agents. I was told I was the only ‘T.’ I was very impressed that the company was that forward thinking.”
Jones is licensed to sell life, long-term care, and health insurance, and well as annuities. “I have a job now with a huge, established company,” Jones says, “and they hired me as me. That wouldn’t have happened eight years ago. I wouldn’t have been ready. I’m very excited.”