I showed up at Ana Winn’s motel room unannounced on a stressful day in June 2023. I was reporting on the first of many waves of evictions from motels as Gov. Phil Scott’s administration scaled back the pandemic-era emergency housing program. Winn had been ordered to vacate her room in a couple of hours. She had been scrubbing the counters with a sponge when I introduced myself.
“Come in, come in, come in,” she said. “Have a seat, honey!”
Winn was a big woman wearing a bright purple patterned dress. “Let me get my glasses on so I can see you,” she said. Her glasses, also purple, were missing one of the arms and lay crooked across her nose. She plopped onto her bed and gestured to an open two-liter soda on her nightstand. “Can I offer you some ginger ale?” she asked.
I’d met Winn, then 57, through her husband, 33-year-old Tony Pickard. Minutes earlier, I’d spotted Pickard walking toward a row of storage units behind a Denny’s in South Burlington. He was pulling a utility cart piled with clothes and cleaning supplies. Meek and friendly, Pickard mentioned his wife over and over. He credited her with helping him kick his meth addiction years earlier. Now she was planning the couple’s next move upon getting notice to leave the Travelodge, where they’d been living for eight months.
Winn had good news for her husband. She’d spent the morning on the phone with a state official named Clark and managed to get them a temporary room at a motel down the road, in Shelburne. They wouldn’t have to pitch their tent at the waterfront for another month.
“Clark is the bomb!” Winn yelled.
She rejoiced like someone singing a praise song: “When I heard his voice, I knew. Thank God, we’re gonna be OK! Thank God, we got Clark!”
Thousands of people have lived in state-funded motel rooms and tents across Vermont in recent years. They’re largely a faceless constituency, seen by many as either a scourge or an object of pity. But each person has a story. In my time reporting on homelessness, I’ve come to appreciate how interesting and messy their lives tend to be. Few have been as memorable as Winn and Pickard, a conspicuously odd couple who built a life together using little more than Pickard’s devotion and the force of Winn’s personality.
The couple came to Vermont in summer 2022 from Tallahassee, Fla., where they’d met on the street. Winn had done her research and knew that Vermont provided comparatively generous food stamp benefits. She figured they could eventually get back on their feet.
First they pitched a tent in the middle of Waterfront Park. The City of Burlington’s lead urban park ranger, Neil Preston, got word that two new arrivals had made camp in the high-traffic area. He walked over and encountered Winn lying on her stomach on the green, placidly reading a Stephen King novel, looking like a college student.
Winn spoke adoringly and protectively to the park ranger about her partner, Pickard, who has a thin, scraggly appearance, lives with schizophrenia and possesses an earnestness that makes him prone to exploitation on the streets.
“She was really struggling with the way people looked down on Tony when they walked by,” Preston recalled.
One day that summer, Winn and Pickard made their way to the small thrift shop inside the First United Methodist Church in downtown Burlington. A volunteer at the shop tapped pastor Kerry Cameron and told her, “There’s a couple in here I think you should talk to.”
“We fell in love with these two birds. And as a result of that, we’ve all felt this real calling to help the homeless.” Pastor Kerry Cameron
Cameron met with Winn and Pickard in the church choir room for an hour. Winn did most of the talking, offering the blue-haired pastor her thumbnail history. She had grown up in Panama and later majored in English literature at the University of Florida. She had three daughters but was only in contact with one. In Vermont, she and Pickard saw an opportunity to change their lives.
I’ve tried to trace the path of Winn’s journey northward. I learned she was born in the U.S. but spent her childhood as one of thousands of “Zonians” who lived in the Panama Canal Zone during its near-century under American control. She was the child of two wealthy Panamanian parents who left her to be raised by her stepfather, according to a childhood friend, Tonya Penney.
At her small school on the Atlantic side of the canal, where American military kids mingled with those of rich Panamanian families, Winn was smart and athletic. She happened also to be chubby, which Penney said made her stick out in a place where teens wore bikinis year-round. Winn, with her booming, ebullient voice and affinity for makeup, anchored the cheerleading squad anyway, Penney recalled.
When Winn turned 18, Penney said, her stepfather bought her a plane ticket to Florida, where she was to live with an aunt she barely knew.
Winn became a student and mother, but stable work doesn’t appear to have been her strong suit. Her middle daughter, Sydney Rae Winn Miller, told me that her mother had worked as an English teacher and tax accountant, among other jobs. When Penney visited Winn in 1998, her friend was living in an apartment in Gainesville and working for a phone sex service, taking calls at all hours of the day in English and Spanish.
By her fifties, Winn had become homeless, Pickard told me.
A meth addict, he met her as he was walking in a park to bathe in a sink one day. She was painting on a bench. She paused and offered him a peanut butter and jelly sandwich.
“I remember it as being so dry,” Pickard said. He still appreciated the gesture. Sometimes he went without food.
The two became friends and later fell in love. Winn taught him some street sense and urged him to stop using methamphetamine. Before meeting her, Pickard said, “I was on my way to death.”
After visiting with pastor Cameron, Pickard and Winn joined the Burlington church, though they sometimes had to take turns attending services so the other one could guard their belongings at their campsite. Soon the church began hosting regular events called “the Share,” where homeless guests are invited to eat a hot meal and tell their stories to church members.
“We fell in love with these two birds,” Cameron said. “And as a result of that, we’ve all felt this real calling to help the homeless.”
“She was the coolest person I ever met in my life.” Sydney Rae Winn Miller
In April 2023, Pickard and Winn got married in the church. Cameron officiated, and Miller and Winn’s then-3-year-old grandson, GianLuca, came from California. Before the ceremony, Pickard went to Applebee’s with a couple of groomsmen, one of whom was Preston, the urban park ranger. Some of the church’s older members served as bridesmaids, and a little dog named Maggie Mae carried their rings down the aisle: a mood ring for Pickard, a band made of Hawaiian koa wood for Winn.
Afterward, they all partied at the church. Guests enjoyed peanut butter and jelly sandwiches that were fresher and more evenly smeared than the one Winn had offered Pickard in the park.
When I met them at the Travelodge a few months later, Winn had big plans. Since apartments in Vermont were so expensive, she explained, they were planning to move to England, where she thought they could rent a two-bedroom flat for $500 per month. “Thank God, I won’t be homeless there,” she said.
They would be able to afford the move thanks to a friend they’d made at the Travelodge who was due to receive almost $23,000 in back benefits from the U.S. Social Security Administration, Winn explained.
The move to England eventually transmuted into a road trip down the eastern seaboard, that friend, Emily Quinn, later told me. The trio rented a car and treated themselves to hotel room stays during the monthlong adventure. They visited Coney Island in Brooklyn and rode the Ferris wheel. Pickard is scared of heights, so, naturally, Winn made a point to rock the compartment as much as she could.
Quinn had to cut short the trip, and Pickard and Winn returned to Vermont, where they still had nowhere to stay.
Winn called me last summer during one of their motel room shuffles. Unless they were able to sort out their eligibility, Winn and Pickard were planning to camp near the waterfront again. If that happened, Winn said, I could join them in the woods for pachamanca, a Peruvian speciality of meat and root vegetables cooked over a pit of hot stones.
During that call, an otherwise jolly Winn told me that she had been diagnosed with cancer the previous fall. She was undergoing chemotherapy, pushing doctors to try every treatment at their disposal.
Winn posted to her social media accounts about the hair loss that followed. The pain became severe, and Pickard pushed her to doctor’s appointments in her wheelchair. They eventually landed in a Motel 6 in Colchester.
I called Winn last month while reporting a story about deaths of homeless Vermonters. Working with a colleague at Vermont Public, I’d been combing records to identify 82 people who had died while homeless in recent years. I thought Winn might know some of them.
She was as cheery as ever. But her cancer, she told me, was now considered terminal, and she was out of therapies. Winn said she was raising money to return to Panama so she could die in her homeland. Sure enough, a GoFundMe started by Penney had raised over $1,000.
“I want to see you!” Winn told me. She invited me to lunch before she and Pickard departed — more specifically, she invited me to buy her a $10 chicken sandwich at Applebee’s. It came with fries, she added.
Busy with my story, I didn’t take her to Applebee’s, and Winn didn’t end up going home to Panama. She died in their motel room on February 23. She was 59.
Pickard took a photo of his wife the night before her death. Winn had an oxygen mask over her nose and both middle fingers in the air. She was flipping the bird to President Donald Trump, Pickard explained.
Seeing that photo left me wishing I’d made time for lunch.
Cameron is helping Pickard make funeral arrangements. The pastor is also trying to connect Pickard with social service agencies that can help him navigate homelessness alone and find somewhere permanent to live, ideally in a group home. It won’t be easy. In the meantime, the church will host a public funeral service for Winn on March 15 at 3 p.m.
Winn’s middle daughter, Miller, said she hopes her mother’s death is honored with celebration, not mourning.
“She was so mesmerizing,” Miller, 32, told me last week from California, where she lives with little GianLuca, who Winn named. “She was the coolest person I ever met in my life.”
Miller hopes to take a trip someday to Panama, where she would scatter her mother’s ashes.
The original print version of this article was headlined “From Florida, With Love | A homeless couple came to Vermont for services. They found a home.”
This article appears in Mar 5-11, 2025.
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