Winter Park Police try to help homeless one person at a time

A new unit aims to connect people who are living on the streets with organizations that can provide new IDs, food, health care and other resources

June 6, 2025

By Kathryn Brudzinski 

Winter Park Police officers Kyle Liquori and Rick Thomas made their way on foot on a recent afternoon to a weed-infested alcove tucked under the Rev. Kenneth C. Crossman railway bridge over U.S. 17-92. 

The officers found what they were looking for just out of plain sight from drivers whizzing along the busy stretch near the border between Winter Park and Maitland –  an overturned shopping cart surrounded by empty tuna cans, batteries, plastic plates, a dirty blanket and a weathered library book amid a pile of trash and abandoned belongings.

“You can see they killed all the grass there,” Liquori said, pointing to a patch of packed down dirt. “You can tell someone’s been sleeping there recently.” 

“Don’t think anyone’s here now, though,” Thomas said, leaning past the sidewalk railing for a better look.

It’s one of the signs of homelessness that’s become as familiar to the pair of officers in recent months as the oak-canopied brick streets and old Florida mansions that often define Winter Park. 

Liquori and Thomas make up the police department’s new Homeless Advocacy Response Team, a program Winter Park tested last year and started up again in February with the help of a federal grant. 

The idea combines elements of policing with potential aid for one of Central Florida’s most intractable problems. As soaring housing costs across the region have pushed more people out of a stable place to live, Liquori and Thomas are patrolling the streets to connect people with help rather than arrest them for crimes.  

“This is the side of things that people don’t see a whole lot of the time,” Liquori, standing in the shade of the bridge. “You’re driving, going to work, and you’re not really looking up here, right? But there’s plenty of places like this.”

The start of the officers’ new roles happened to coincide with a new Florida law that bans sleeping on public property. 

So far the pair haven’t made any arrests related to public camping, they said. Many of the camp sites they find are on private land in wooded areas or hidden behind gas stations or other businesses. But the new state mandate has complicated their mission.

“It’s tough,” Liquori said. “When we go out, we have to inform them of the law. That’s our job first and foremost as law enforcement officers. But then we’re trying to help them out, too, so it’s a fine line.”

The officers set out on the special patrol four days a week, typically starting at 6 a.m. when those who slept outdoors for the night are more likely to still be at their camps. 

HART, the department’s shorthand for the program, aims to give time for officers to build one-on-one relationships with people they find on the streets. A little trust and familiarity, the officers said, goes a long way when a person is trying to decide if they will accept help from other groups that can provide meals, clothes, mental health services or housing. 

“It can be hard to get through to those people and say, ‘Hey, let me help you,’” Liquori said. “Let’s go get you a hot shower, let’s go get food or get laundry done. They’ve had to do things by themselves for so long, they’re going to continue to do things by themselves.”

Both men wear polos and khakis with protective vests and carry their department-issued firearms. They drive a marked pickup truck without the barrier that separates officers in the front of a patrol vehicle from passengers in the backseat. They say they use water bottles, cleaning wipes, tissues and more from the supply stock they carry than they use handcuffs.

Driving through the city on a recent Monday, they showed a reporter their typical route, which often focuses on the east side of Winter Park. They encounter more people there, usually more men than women and usually middle-aged or older. 

“As we help one or two people out, we’ll see two new faces,” Liquori said. “It’s a revolving door, at least three to five people a day that we’re getting out with and talking to and helping.”

Homelessness isn’t new, especially in Orange County, where hourly wages are lower than the national average and rents soared after the pandemic. 

Winter Park’s Brookshire Elementary, Lakemont Elementary and Winter Park High School this year tallied a combined 10 students living in motels, one in a shelter and 76 bunking up with another family or other shared arrangements, according to records from Orange County Public Schools. 

Eric Gray, executive director of the Christian Service Center for the Homeless, said the number of people in need of permanent housing is steadily increasing. 

“Nationally, the overall number of people experiencing homelessness on a single night in 2023 was about 650,000, but in 2024 that number went to 770,000,” Gray said. “That increase compared to the rest of the population means it’s the highest percentage of the population in the United States experiencing homelessness since the Great Depression.”

Liquori and Thomas said they’ve noticed it’s easier to help people who are newer to sleeping on the streets than those who have lived without a permanent residence for a long time. 

“The longer you stay in that cycle, the harder it is to come out of it,” Liquori said. “When we get out with people that are recently homeless, we have a greater success rate of them accepting resources or them getting the help versus people that have been homeless longer.”

The pair said they see the toll homelessness takes on the mental and physical health of people they meet and they are mindful that some people may have had negative interactions with police in the past. 

Being homeless can “consume” a person, Liquori said, when that person’s priorities are reduced to simple survival while potentially dealing with mental health, physical disabilities or addiction issues.

“For some people, they’re just trying to get along and get by their day,” Thomas said.

That’s why the officers said they don’t force anyone to accept help. But in cases where someone is willing, the officers show them a list they created, and routinely update, of organizations like The Sharing Center, Family Promise of Greater Orlando or the Samaritan Resource Center and give them a ride to the place of their choice.

“We never force anyone to go to get help anywhere,” Liquori said. “We’re trying to establish more relationships with people on an individual level. We’re walking up to the front door, we’re introducing them to the intake person. We’re doing a better job exchanging hands, that way they get the care and the resources they need.”

The interactions mean Thomas and Liquori get to know some of the “regulars” they encounter on patrol and check back in on them. After months on the job, they know where to look – certain street corners, wooded areas behind gas stations, the hidden nooks under overpasses. 

One such regular, they recalled, is a man who they learned is a veteran named Eugene. He told them he became homeless years ago after he fell from a ladder and was injured. 

“He just didn’t have the insurance to have coverage,” Thomas said. “He was an hourly employee, fell behind and became homeless. You know, you get hurt and can’t work for a couple of months and then your employer lets you go.”

They said they found out the man could possibly qualify for housing through the Pathlight HOME organization in Orlando, but he didn’t have his military discharge paperwork or other documents. 

Thomas drove him to the Lake Baldwin Veteran Affairs Clinic.

“The first day he initially went there to get his paperwork and he ended up getting some prescriptions that he needed filled and got some medical treatment,” Thomas said. “He didn’t get the paperwork that day, but at least he got what he needed. I came back and picked him up and gave him another ride another day to actually get his paperwork.”

Many of the people they encounter are in a similar situation – they’ve lost their official identification and other documents they need to get a job or access to services. The officers say IDignity, a local nonprofit that helps people recover proof of identity, has been helpful. 

“That’s the problem if you’re homeless and you lose your paperwork or ID, you don’t have anything to get another one,” Liquori said.

Gray said cities like Winter Park must also confront the “horror” of homelessness by investing in more services within its borders and by helping to create more affordable housing. 

Of the more than a dozen charitable organizations and resource providers on the Winter Park Police website for homeless resources only two of those have Winter Park addresses: Jewish Family Services of Orlando and Greater Promise of Greater Orlando.    

“These are the last things that communities like Winter Park want to be doing because they attract the very element that they don’t want in their community,” Gray said. “But the reality is that the people who are homeless right now in Winter Park were, 90 percent of the time, last housed in Winter Park.”

He said Orange County’s affordable housing deficit is about 75,000 units. The greater Orlando area ranks as one of the worst places in the nation for affordable housing. For every 100 extremely low-income renters, the region has just 19 affordable and available units, according to a new report on the housing gap from the National Low Income Housing Coalition. 

“We’re growing further out of balance,” Gray said. “It’s going in the wrong direction. There’s very few places available in the community that people can legitimately afford without spending almost half or more of their income on rent or even a mortgage.”

He said his organization has seen law enforcement units take more action since Florida’s public camping ban took effect to clear out places where known encampments are set up, even for a single individual. 

“They’re not being rude or aggressive about it, they’re just abiding by the law and the way that it’s written now,” Gray said. “Law enforcement officers are the ones that are the most unhappy about it from our experience. None of them decided to become a police officer because they could help move homeless people along to another place.”

Liquori and Thomas have seen it, too. They recently discovered that a homeless camp just out of their jurisdiction on a pond and hidden behind a tree line had been cleared away.

“Orange County or someone must have come here and cleaned the camp out all on the back,” Thomas said, pointing out a newly installed no trespassing sign from the Florida Department of Transportation. “There were 15, maybe 20 tents back here. We haven’t been back here in a couple weeks … but it looks like it’s all gone.”

The change made Liquori pause. 

“They kind of had a somewhat permanent place to stay, but now they’re just roaming the streets,” Liquori said. “It’s tough, you know? What’s better?” 

Liquori and Thomas often take on the responsibility of cleaning up camp sites they find on public property in Winter Park, loading stolen shopping carts into the bed of their truck to return to stores and clearing away trash and other abandoned items. 

“Yeah, it’s dirty and disgusting and someone has to clean this up,” Liquori said, looking at a plastic sleeping mat hidden in the trees at another camp near Interstate 4 and Fairbanks Avenue.  “But someone was living back here at some point, you know? That’s the real sad part. This was someone’s home.”

WinterParkVoiceEditor@gmail.com

Kathryn Brudzinski is a reporter based in Orlando and a University of Central Florida graduate with a degree in journalism, as well as a certificate in public and professional writing. Her work has appeared in Oviedo Community News, VoxPopuli and The Charge.