Allegheny County Jail's new warden draws praise, even from the lockup's fiercest critics

Being in charge of the Allegheny County Jail means running from meeting to meeting.

But on Fridays, Warden Trevor Wingard slows down to a walk.

At the end of each week, Wingard strolls from floor to floor of the 16-level lockup, taking the pulse of the beleaguered facility he’s been tasked with changing.

Racking up 7,000 to 10,000 steps on his rounds, the new warden chats with corrections officers, checks the housing units for problems and answers questions — lots of questions — from those incarcerated.

During a recent Friday walkthrough, a TribLive reporter accompanied Wingard and chose the stops on the itinerary: the juvenile pod, intake, the mental health unit and the women’s section. The warden frequently paused to shake hands and introduce himself.

“Hi, I’m Trevor, nice to meet you,” he said to a woman who was interviewing to become an art teacher at the facility.

The warden swapped small talk with staff and officers, greeting many by their first names. It was clear they were familiar with the warden, and he with them.

Dressed in business clothes, Wingard cut an unassuming figure. Approachable, interested and willing to engage, Wingard represents a sea change from how his predecessor ran the jail.

Under the prior warden, Orlando Harper, tensions were high. Harper’s tenure was plagued by a high suicide rate on the pods, complaints about poor communication with family members of incarcerated people, friction with an oversight board, allegations of discord between unionized employees and administrators, and lawsuits for a range of alleged abuses.

When County Executive Sara Innamorato took office in January 2024 after 12 years of the previous administration, she set out to transform the county’s corrections culture.

A year later, Wingard was hired to fix problems at the jail, which sits on the edge of Downtown Pittsburgh.

Wingard, 56, has built his career in corrections, rising through the ranks of the state prison system. He ran nine facilities as a deputy corrections secretary before retiring in 2022.

Now, more than 100 days into his tenure, Wingard is drawing praise from even the facility’s most ardent critics. In a dozen interviews, observers including activists, lawyers, subordinates and a union leader said Wingard is making a positive difference. He’s putting his decades of experience into practice, using a personal touch to make connections and shake things up.

During the depths of winter, for instance, as Wingard walked through a first-floor pod, an incarcerated woman asked him to step into her cell so he could feel how cold it was. He did — and immediately set into motion moving the women to the warmer sixth floor.

It was a small thing. But for the woman, it was meaningful.

Sometimes, Wingard joins teens on the juvenile pod for basketball in the small gym on their unit. He often eats lunch in the staff cafeteria.

At the women’s pod with its 192 residents, Wingard was treated somewhat as a novelty during the guided tour with a reporter. Several women approached him, asking who he was. Once they found out, they fired off questions.

Some were as simple as, “when is my hearing?” Others asked about visiting a dentist or becoming a pod worker.

Wingard took his time answering.

After, he declared, “Clearly, that’s my next priority — female unit manager. I need more of a presence on the female unit.”

All of it — the walking around, the visiting, the chatting — stands in stark contrast to Harper’s style.

Harper could not be reached for comment. His former boss, Rich Fitzgerald, the previous county executive, declined to address criticisms of the jail’s operation during his administration.

The changes under Wingard, staff and volunteers say, signal hope for the future.

“It’s not all fixed yet, but we’re finally seeing steps toward fixing the issues,” said Bethany Hallam, a County Council member and outspoken Jail Oversight Board member who once was incarcerated at the same jail she now helps to oversee. “It’s more than I could have imagined.”

Nothing to hide

Wingard views his duty as improving conditions for everyone, said Connie Clark, the jail’s deputy warden of programs and services.

“In every decision, how do we make things better for the people who live here and the people who work here?” Clark said. “It’s a theme in everything we do.”

As part of that work, Wingard keeps a white legal pad on his desk with dozens of items on a to-do list. The list, he said, will always exist, although it evolves and changes with each accomplishment.

On Wingard’s 100th day on the job in late April, the jail hosted a volunteer banquet for the first time in recent memory.

Organizing the event to honor about 150 people who provide critical services at the jail was one of Wingard’s first priorities when he took over, according to Clark.

Volunteers are often forgotten, Wingard said, and he believes they should be recognized.

“I thought it was time to say thanks to people,” he said.

Tanisha Long, an advocate with the Abolitionist Law Center — an organization that has sued the jail at least a half-dozen times — attended the banquet.

“Just doing that shows they understand they can’t do this work without the community,” Long said. “He’s demonstrated he’s willing to bring the community into the jail.”

Wingard said he hopes to hold open-house events — for the media, the area’s legislative delegation and employee families.

“We have nothing to hide here,” he said. “There’s nothing I’m afraid for anyone to see.”

Visible man

One of Wingard’s top priorities was improving relations among the 800 members of the jail’s staff — with each other and the administration.

The warden urged his communications staff to expand their one-page bulletin each month into an employee newsletter focusing exclusively on staff and invited employees to write for it.

The effort is an attempt to eliminate what Wingard sees as employee factions.

“I felt like there were a lot of silos here,” Wingard said.

Wingard believed the staff was clamoring for a change. That’s why, Clark said, he spends so much time walking around the 30-year-old facility and trying to connect with people.

“He’s approachable that way,” she said. “He’s open to feedback. He’s willing to hear the bad, as well.”

Brian Englert has been president of the Allegheny County Prison Independent Union for four years and frequently was at odds with the previous administration.

While acknowledging frustrations still exist among union members, Englert praised Wingard’s openness and leadership style.

“Overall morale in the building has improved drastically,” he said. “When you walk in, you’re not walking on eggshells like the last administration.”

Like Clark, Englert attributes the change to Wingard’s willingness to spend time with the staff on the units. He sometimes makes rounds early in the morning or late at night to interact with officers on those shifts.

“He goes out of his way to make sure people in the building know what he’s thinking,” Englert said. “This guy is visible. He’s out talking to people, asking how your day was. That’s what he said he would do, and I’m ecstatic that he does.”

Getting to yes

Wingard’s impact has been tangible. Englert said officers have complained for years that the two vans they were forced to use for medical transports were unsafe. When they approached Wingard about it, Englert said, they had two vehicles in less than two months.

Jail leadership is now coaching younger corrections officers when they make a mistake, Englert said, instead of immediately issuing discipline.

Wingard has created an intelligence team to stop the flow of weapons and drugs into the jail.

Englert said one barometer of success will be reflected in staff retention. Seventeen correction officers graduated from the academy on May 30, Englert said, bringing their total complement to 389. Another class of 30 is starting this month.

Wingard hopes a policy he has implemented — quarterly check-ins with first-year officers — will help jail administrators stave off departures.

In prior administrations, said Rob Perkins, a criminal defense attorney and member of the Jail Oversight Board, it seemed the staff was not treated with respect, which led to an unhealthy culture that negatively impacted the people incarcerated there.

Wingard said there will always be some jail employees who are set in their ways.

“There’s a lot of unlearning that has to happen,” Wingard said. “We’re going through a lot of that right now — just because it was done that way before doesn’t mean it has to be that way.”

As new ideas work their way through the staff, the warden said, he sees officers feeling empowered in their positions. He often hears “‘we were never allowed to do that before.’”

“People are now responding — ‘how can we get to yes?’ — instead of the hurdles,” Wingard said.

‘Refreshing change’

For years, monthly Jail Oversight Board meetings were fraught with hostility among board members, jail administrators and the public who attended.

In just four months, said Allegheny County President Judge Susan Evashavik DiLucente, who chairs the meetings, Wingard has reduced the conflict.

“The guy is the best thing to happen to Allegheny County Jail in decades,” Evashavik DiLucente said. “It’s such a refreshing change.”

One stark difference is simply in how Wingard conducts himself at board meetings.

During public comment, people often talk about problems involving their incarcerated loved ones, such as accessing medication, lacking food or being maltreated by officers or others who are incarcerated.

Harper, who retired in September 2023, would not look at those who spoke or engage them. He faced forward or kept his head down.

Wingard turns his chair toward speakers. He watches them. He takes notes. He sometimes seeks them out after the meeting.

Evashavik DiLucente described Wingard as a down-to-earth person who tells it like it is.

“He’s smart, he’s thorough, he’s responsive,” Evashavik DiLucente said. “We don’t have to ask him. He tells us.”

Harper often evaded questions from board members, citing “security concerns.”

Wingard provides thorough answers.

“I do think it’s a night-and-day change in the approach to the jail,” said Erin Dalton, the county’s director of human services, which works closely with the jail. “Everything is easier. The friction amongst all of the partners is lower, and that matters.”

Changes underway

Wingard has promoted three people to newly created unit manager positions. He calls them “mini wardens.”

One, Gerald Roundtree, runs the juvenile pod. He said he’s working to make the teens there — 17 as of early May — feel a sense of ownership.

When it was time to repaint the drab gray-and-white pod, Roundtree — with Wingard’s permission — let the teens pick the colors. They chose bright blue and tan.

“It gives them a sense of self-pride,” said Roundtree, who spent 22 years with the state Department of Corrections before joining the jail two years ago. “They take care of it way better.”

Not long after Wingard started, he stopped by the juvenile pod during a basketball game. The warden asked which teen was the best shooter and made a deal: Hit a shot from the spot Wingard picked, and he would have a broken Xbox repaired for them.

The teen made the shot, and Wingard made good on his pledge.

Those kinds of moments, Wingard said, can help ease the pressure and stress of incarceration — and make everyone’s job easier.

Heather Greenawalt spent 10 years as a unionized sergeant and was still in that role when she took Wingard on a tour of the intake unit. She identified problems, and he asked if she’d take a promotion to captain and unit manager.

She said yes.

“In this short time, he’s given me the ability to fix things,” Greenawalt said. “I left the union to be a captain. That’s how much I trust (the leadership team.)”

Evashavik DiLucente praised Wingard for making substantive improvements such as revamping the intake process, where arrestees have their first contact with jail staff.

Perkins, the defense lawyer and board member, mentioned to Wingard early on how the previous jail administration barred legal visits between attorneys and clients during large chunks of the workday.

“Security shouldn’t be an excuse to say no to everything,’” he quoted Wingard as saying. “A week later, he changed the policy and now clients are much more able to see their attorneys quicker.”

Wingard has tasked his administrators to review the jail’s current policies with an eye toward staying at the forefront of changes in corrections.

“He pushes us to get out there and learn about what’s happening nationally and bring it back,” Clark said.

Chief Deputy Warden Lee J. Estock has been at the jail for two years following a 24-year career with the Pennsylvania Department of Corrections.

He called his boss — who he’s worked for six years dating back to their state prison time — even-keeled, creating a “calming effect.”

A pleasant surprise

Hallam, the County Council and oversight board member, regularly sparred with the previous administration. She publicly called out Rich Fitzgerald, the former county executive, for failing to attend monthly meetings as required by law, and once used vulgar language to insult a former board chair.

Hallam said having Wingard in charge is the next best thing to not having a jail.

“I would love to give a both-sides interview,” Hallam told TribLive. “But I don’t have another side. I don’t have anything bad to say about him.”

She compared Wingard to “your friend’s dad.” He’s welcoming and friendly, she said, and always willing to help.

“He’s open and responsive,” she said. “If you ask him to check on something, he does.”

Long, of the Abolitionist Law Center, said that her organization’s goals are to stop deaths in the jail and improve conditions there.

“No one warden is going to do that, but I have been pleasantly surprised at the gains we’ve made,” she said. “It would be a lie to say things haven’t gotten significantly better.”

Among those improvements, Long said, incarcerated people and their families are better positioned to advocate for themselves.

Part of it, Long said, is that the new administration is no longer combative.

“We don’t have to fight about every little thing.”

Still work to do

In May 2021, Allegheny County voters overwhelmingly approved a referendum forbidding jail officers from using leg shackles, pepper spray and a device called a restraint chair.

That restriction has greatly inhibited officers, according to Englert, the union head.

Evashavik DiLucente believes such a referendum would never have been necessary had Wingard been in charge.

“It was a desperate attempt to end the abuses going on down there,” she said.

The referendum created new problems, though.

The jail is now the only facility in the state where officers can’t use pepper spray, according to the judge. And she said the inability to use leg shackles means the jail needs to send two officers for any incarcerated person’s out-of-jail medical visits, increasing manpower and costs.

“They’ve lost tools that were necessary,” she said.

There are other problems, too. Long still hears complaints about health care problems, such as delays in sick calls being answered and medications not being passed in a timely manner.

There also continue to be too many lockdowns, Long said.

Long is curious how Wingard will navigate these and other challenges.

“A lot of tests are coming up to see how he does,” Long said. “What he’s doing so far is absolutely a step in the right direction.”