It’s after midnight at The Warren Bar & Burrow, one of the only two spots in Downtown open this late in the middle of the week.

Dozens of people pack the space on the corner of Liberty Avenue and Seventh Street. Colleagues attending a nearby convention huddle around tables, service workers whose shifts have ended swivel in their chairs at the bar and grad students camp out in the booths. The voices all try to outmatch the sounds of Fleetwood Mac blasting out of the bar’s speakers.

Cortney Buchanan, bartender, manager and partner, maneuvers behind the bar. He and the other servers glide past each other as they take turns grabbing orders, stirring up old-fashioneds and closing out tabs.

You wouldn’t know it by the smile on his face, but it’s Mr. Buchanan’s eighth hour of work and he has two more to go.

“When someone asks their bartender where they should go, we get the recommendation. Then an hour and a half later, when [the bartenders are] done closing and cleaning, they come over here,” Mr. Buchanan says.

Over the course of one hot, sticky day in July, the Post-Gazette sent about a dozen reporters and photographers into the pockets of Downtown Pittsburgh that most people see only in fleeting glimpses — perhaps as they head to office jobs on a Wednesday morning, go to an afternoon Pirates game, or catch a show at the Benedum Center.

It’s not the same Downtown that Pittsburghers in the 1970s or the 1990s saw or even that those who were in the Golden Triangle back in 2015 recall.

But it is still the hub of Western Pennsylvania, the home to the NFL team named after the steel industry that helped make many Pittsburghers rich a century ago and that convinced the professional football league to hold draft festivities here next spring.

Evidence of past concentrations of powerhouse businesses Downtown still echoes in the names — the Gulf Tower, the Frick Building, the U.S. Steel Tower, and even the one at 11 Stanwix that many still call the Westinghouse building. Banks still carry weight here, with FNB not long ago putting its name on the new skyscraper where the Penguins once played and PNC Financial Group plopping its 33-story headquarters in the center of Downtown just a few years before the pandemic began emptying out offices.

The Cultural District theaters bring in crowds, while decisions made years ago to play baseball games and football games a short walk across the Allegheny River keep tens of thousands of  Western Pennsylvanians coming back — at least once in a while.

Next April, the NFL Draft is projected to bring in 500,000 to 700,000 visitors, according to Visit Pittsburgh, and generate millions of dollars in economic activity. That is seen as an energy drink that might help change the momentum Downtown. Using the party as incentive, state and local officials have laid out a strategy meant to spruce up public spaces, build new ones and convert office spaces into residences in the city’s center.

Safety is an ongoing touchpoint. It helped drive the February 2024 opening of a Downtown Public Safety Center on Wood Street, and each period of relative calm quiets the debate can be quickly upended by an incident that draws the public’s attention. On this July day, the subject will resurface in conversation numerous times as Post-Gazette reporters move through the city center.

Several days later a shooting near the corner of Ninth Street and Penn Avenue — one that occurs in daylight hours — would wound a man and a woman, leading Mayor Ed Gainey to issue a statement. “Pittsburgh remains resilient, united, and committed to ensuring that every neighborhood, including our Downtown, is a place where people feel safe, supported, and can enjoy all our City has to offer.”

Back at the Warren, regulars and new blood still swarm the bar each night, although Mr. Buchanan reports he has seen customer traffic decline since the pandemic.

The rise of hybrid work and the subsequent dip in the number of suit-clad office workers coming for a noon-time bite has kept the lunch service shut since 2020. 

“We used to have a really good lunch that would kind of segue into the night time crowd,” Mr. Buchanan says. From baseball players still in uniforms to tourists dressed up for a show at the theater, the bar was always bustling with a diverse crowd of customers.

Mr. Buchanan has been working at the Warren since 2018 and bartending for over 20 years. Before coming Downtown, he worked in the South Side.

Some there warned he would have to leave his “smart-ass” sense of humor behind to cater to a “very stuffy” Downtown crowd. “[They said] you can’t be the type of bartender you are in the South Side, Downtown. They won’t put up with it,” he says.

But, he adds, “I haven’t changed.”

It’s just one of many misconceptions he says he’s heard about those who live, work and play Downtown. From his vantage point, there’s little to no difference between the Warren’s customers and the ones he served on the raucous South Side. At the end of the day, they all want good drinks, good service and a good time.

“Downtown is not what you think it is, so just come on down,” Mr. Buchanan said. “You’re not going to experience anything you haven’t experienced in another major American city.”

Around 2:15 a.m. on this July day, the Warren begins its quiet transformation.

Employees bustle around the bar, drawing curtains, rolling up mats and wiping down the sticky tables. Syrups and garnishes slosh around in plastic quart containers stacked on the bar counter.

The last few customers nurse near-empty drinks and joke with the bartenders before being ultimately ushered out into the vacant streets of Downtown Pittsburgh.

It’s quiet overnight: Data from the National Incident-Based Reporting System, a nationwide crime data collection system, shows no incidents reported to police in the Central Business District until around 7:40 a.m. when someone is cited for a hitting a parked car in the 300 block of Grant Street.

By 7 a.m., the Downtown streets are filling up again and the early morning office crowd is shuffling in and out of the Starbucks at Penn Avenue and Sixth Street. Baristas greet a few by name. Most collect their orders and promptly get on their way, stepping back out into the warming morning.

A crew of men wearing almost identical outfits — button-down shirts, khaki pants, leather belts and dress shoes — walk in after a woman in a fuzzy maroon sweatsuit with matching Nike Dunk sneakers.

By 7:17 a.m., business is picking up: about 10 people cycle in at any given time. A line starts to form to order, while those who’ve successfully paid for their drinks hover around the pickup area.

Outside, walking uptown on Liberty Avenue, the sun beams down so bright it’s blinding. People clump together on the sidewalk, conversing and blocking foot traffic, as cigarette smoke encircles them.

Roughly 35,300 people flow into Downtown Pittsburgh to jobs each day — office workers headed to the U.S. Steel building or PNC Tower, city and county employees to Downtown’s historic government buildings, and service workers to keep it all running. Attorneys with briefcases trickle into offices in the Grant Building and the Allegheny County Courthouse, a castle-like landmark rising out of the center of Grant Street.

Nearly half of Downtown employees work in finance and insurance or professional, scientific and technical services, according to data from the Pittsburgh Downtown Partnership.

Each workday more than doubles the Central Business District’s residential population, which is just over 21,800, according to the Pittsburgh Downtown Partnership.

That’s still only about 60% of what the employee population was pre-pandemic.

About 20% of Downtown offices are sitting empty, according to Cushman and Wakefield’s second-quarter market report, with developers and city officials now working to reconfigure space and find new uses for buildings once filled with desks, water cooler talk and people in their business casual best.

Not far from the bustle of Wednesday morning work routines, a small group has formed near the corner of the Boulevard of the Allies and Stanwix Street. The line forms there most mornings and again later in the day at the Red Door, a nonprofit that serves two meals a day.

As the line grows, wine-red folding chairs are brought out for some to sit on.

Many sip coffee. Cigarettes are passed among them.

One man in a dark blue basketball jersey and sunglasses plays Rick Ross on a portable speaker. A woman speaks urgently on the phone, asking the person on the other end of the line when she can pick up her dog.

While the group waits for the Red Door to open at 9 a.m., about a dozen men gather in an immaculate dining area on the ground floor of the neighboring Compassion Corner, which offers programs to serve the city’s homeless and provides a space for those who frequent the Red Door to sit down and eat their meals.

At the front desk sits a pile of flyers that provide information about services offered during high-heat alerts. The temperature later that day is expected to be near the 90s.

Moments later, the volunteers arrive.

The Red Door’s corrugated metal window — a flaming heart painted on the front — rattles open as food pantry workers shuttle food from vehicles they hastily park in front, emergency blinkers on. Volunteers bring out individually bagged sandwiches and large canisters of coffee.

As the line for meals grows longer, young professionals in button ups, many with large thermoses in hand, stroll by.

By 10 a.m., chairs line the entire corner, down both Stanwix Street and the Boulevard of the Allies.

A few blocks away at PPG Place, dozens of office workers scurry into the neo-Gothic office buildings that line the square. The sun and its heat beam down off the buildings’ trademark shimmering glass facades. At a table, a woman sips coffee and watches the large fountain in the middle of the square as it pulses streams of water 15 feet in the air.

A handful of couples wearing shirts emblazoned with the Detroit Tigers logo stroll through, staring up at the buildings and taking photos – killing a few hours before their team takes on the Pirates.

By this time, at the River View apartment building with about 200 units across from Point State Park, most residents who use the valet service, Impark, have headed off to work.

Day manager Tom Blackwell leans up against a desk next to the cramped valet office’s rack of car keys, holding a bag of Lay’s sour cream and onion potato chips in one hand and a 7-Eleven Big Gulp slushy in the other. His eyes drift between a clear window facing into the apartment and its doorway out to the parking lot, ready to hop up and move a car at a second’s notice.

The office’s other occupant, Karen Wagner, works the phone as residents call to let the valets know when they will be stopping by.

Mr. Blackwell and Ms. Wagner, known affectionately by their coworkers as the “Dynamic Duo,” have been working identical 6 a.m. to 2 p.m. shifts for the past several years.

Growing up in the suburbs of Jefferson Hills in the 1980s, Ms. Wagner said she and her friends treated Downtown like a place to survive instead of visit, outside of the occasional Pirates game on the nearby North Shore.

“Now it’s so much more welcoming than it ever was — there’s so many more restaurants and things to do down here.” she said. “We would have come Downtown if they had the floating, drinking Tiki boats (The ‘Cruisin’ Tikis’ rental service).”

Mr. Blackwell spent quite a bit more time Downtown during his “troublesome” early years growing up in the Hill District, but he said he’s matured since then. “I straightened up — I would like to consider myself as a citizen now,” he said with a wry smile.

The valet office’s prime location right next to River View’s door means Ms. Wagner and Mr. Blackwell are constantly chatting up passersby.

Ms. Wagner greets some familiar faces, like Iraj Waheed, an incoming first-year medical school student at Duquesne University, and Justin Greenwald, who runs his heating and air conditioning company, MOC Inc., out of an apartment since many of his clients are Downtown.

Ms. Wagner said her office door is always open — a habit that she continued even when she briefly filled in working late-night shifts as she discovered that the crime she feared in her youth wasn’t an issue. “I never, ever felt uncomfortable,” she said.

Some of the “Dynamic Duo”’s other recent interactions bolstered their reputations as jacks-of-all-trades. Mr. Blackwell recalled a recent episode when a young tenant came down to the valet office in tears, not knowing what to do while she was trying to escape a bad situation with a roommate. Earlier that morning, Ms. Wagner had driven a longtime resident, Carol, to work on Grant Street because she recently underwent a surgery and had difficulty traversing Downtown with her cane.

“I feel like that’s what Pittsburgh is … you don’t see too many people that are just downright nasty.”

River View is preparing to transition to self-parking. In a few weeks, Ms. Wagner, Mr. Blackwell and their co-workers expect to be out of jobs.

“We’ve already had a couple residents tear up and start crying, and I’m like, ‘No, not yet, don’t do this to me,” Ms. Wagner said. “I’m getting really sentimental thinking about all the stuff we’ve gone through together.

“I hope Pittsburgh bounces back with more shops and restaurants down here … this is a pretty good town.”

Just outside the Fort Pitt Block House in Point State Park — the oldest standing building in Pittsburgh, if not all of Western Pennsylvania — a bright patch of joe-pye weed, coneflower and nodding onions is buzzing with honeybees. A pair of spirited American goldfinches flits among the blooms.

The flower garden is the handiwork of the Allegheny County Garden Club, which has spent the past five years reclaiming weedy corners and replacing invasive plants with native ones.

The volunteers, mostly senior citizens, come to the park each Wednesday to tend to the plants they’ve worked hard to establish and root out the weeds. On this particular morning, they pack up by about 10:30 a.m. — before the worst of the midday heat can set in.

“The difficulty with native planting is it takes a long time to get rid of the invasives,” said Robin Kamin, 73. “You have to keep up with it.”

She and three other club members are working near a bioswale carved into an embankment to capture stormwater runoff from the Parkway North, the highway overhead that bisects the park. The area is a tangle of thistle and bush honeysuckle.

“When we started five years ago, that area looked worse than this,” said Frank Pizzi, 60, pointing to overgrowth. “It was all just weeds, weeds, weeds.”

Nearby, an Eastern cottontail rabbit darts into the bushes as a cyclist coming off the Fort Duquesne Bridge races past on the Three Rivers Heritage trail.

“This is just a gem,” said Jill Lechner, 65, another volunteer. “To be in the city and be able to have a natural environment is very important.”

By 11 a.m., officeworkers stroll the riverside paths, talking shop with their colleagues. Others sit on benches that overlook the Allegheny River, tuning out the city noise with a book or podcast.

As part of Downtown’s broader redevelopment, more than $25 million has been set aside for Point State Park. That’s in addition to $3.4 million in funding to improve the park’s landscape and infrastructure — lighting, walkways and public amenities — ahead of the nation’s 250th anniversary and the 2026 NFL Draft.

Point State Park is the fourth most-visited state park in Pennsylvania, with approximately 100,000 monthly visitors in the summers, including tourists and locals.

Jack Lachendro, an environmental education specialist at the park, likened it to Pittsburgh’s “front yard.”

For tourists, the park marks the spot where Pittsburgh took root more than 250 years ago, and frames the classic shot of Downtown: iconic fountain in the foreground, skyline in the background, rivers on all three sides.

For locals, the park is familiar ground — a calm pocket in a busy city where folks go to jog, walk their dogs and escape stuffy Downtown offices.

“I can't tell you how many times I've had people say, meet me at the Point and 15 minutes later, their friend shows up,” Mr. Lachendro said, adding, “I’ve seen marriage proposals here. I’ve seen breakups here. I’ve seen family reunions. I’ve seen kickball tournaments. I’ve seen festivals.”

A delivery driver from Tom Friday’s Market pops into Nicky Geanopulos’ office to say hello and drop off an invoice for a shipment of beef and chicken from the beloved Brighton Heights butcher.

Unlike most modern-day diners, Nicky’s Grant Street sources most of its proteins fresh and unprocessed. The kitchen breaks down whole chickens for its breakfast and lunch dishes as well as daily specials such as chicken Milanese. Ground beef goes into a custom burger blend popular with regulars.

Mr. Geanopulos’ office — walls stacked with photographs of local and national politicians of all stripes, including several past presidents of the United States, as well as a host of global celebrities and famous Pittsburghers — is the 77-year-old’s command center. His field is the floor of the multi-room restaurant he’s run since 1984.

“In a way, I'm a master of ceremonies here,” he says as he begins to make the rounds chatting up regulars who are starting to file in for lunch hour.

“We have lawyers, judges and political staffers in here right now. Tourists, too.”

Tuesdays through Thursdays between noon and 1:30 p.m. are the busiest hours these days at Nicky’s, which is open for breakfast and lunch.

Mr. Geanopulos says the shift in post-COVID dining is noticeable, with fewer people working Downtown five days a week and breakfast outings falling out of fashion. Huntington Bank moving its branch office and 200-plus employees from the first floor of the building to the Strip District didn’t help.

Nicky’s doesn’t have a street-facing entrance — getting in requires entering the Grant Building, ascending a small staircase and turning right — so it’s long drawn a good portion of its clientele from those working in or near the skyscraper.

“We're still making it work. We do everything we can to satisfy the customers and it shows,” he says.

As Mr. Geanopulos points out the favorite dining spots of a litany of former Pittsburgh mayors — Sophie Masloff liked to sit in a tiny nook on the far side of the counter so nobody would bother her unless invited; Richard Caliguiri enjoyed a seat at the counter closer to the kitchen — one of their progeny takes a seat nearby.

“Why aren't you sitting in your dad's seat?” Mr. Geanopulos asks David Caliguiri.

“That was his seat. I like to sit a few places down,” he replies.

Mr. Caliguiri likes to come in as often as he can. Like many of the guests that Mr. Geanopulos is making conversation with this afternoon, he’s a regular because the place feels like eating with family.

“You always see someone you know. Everyone eating in here makes you feel like you're part of something, which is something Downtown is lacking lately,” he says.

Mr. Caliguiri, a fan of the tuna melt but always open to trying something different, orders the chicken Milanese. It’s one of several specials from Tamara Molnar, a nine-year employee who serves as Nicky’s right hand.

“Quiche Lorraine, chicken Milanese, we have some nice croissant sandwiches and a bread pudding,” Ms. Molnar says. “I like to keep things fresh so we always have a few specials in addition to the regular menu.”

Another longtime regular, criminal defense attorney Wendy L. Williams, stops in a little after 12:15 to pick up lunch to bring back to her upstairs office. Sometimes, she gets takeout, sometimes she sits by herself and sometimes she hobnobs, just as she’s done since the day Nicky’s opened.

“You can see how the fabric of the city of Pittsburgh is built here,” Ms. Williams says. “It’s incredible how much gets done in these booths.”

By 12:30 Nicky’s is nearly full. At this moment, nobody in the restaurant is scrolling a screen on their phone. Most diners are in groups engaged in conversation. One solo guest reads a hardcover book. Another banters with a server at the counter.

Mr. Geanopulos started in the restaurant business in the 1960s, following in the footsteps of his father and grandfather, both of whom ran Downtown eateries going back to the 1920s.

Like his predecessors, he’s seen booms and busts and changes in the way people eat.

Yet even with the rise of third-party delivery apps and hybrid schedules, Mr. Geanopulos is certain there is always a need for a Downtown daytime diner.

“People like to have lunch with each other, people like to talk in person with each other and make deals face to face. That's not going to change,” he says.

A middle-aged man wearing scrubs steps into the store asking for a suit jacket. Thomas Michael, president of Larrimor’s, greets him, whisking the man away to a sales associate near a wall strung with men’s suit jackets.

“Now there’s a man on a mission,” Mr. Michael had said when the customer entered.

On this July afternoon, staff outnumbered customers, though a consistent stream of foot traffic trickled past the front window.

“In 2019, you would walk down the street and all of the restaurants were full, the offices were full, and Downtown was full of energy,” Mr. Michael said. “We think there is a lot of opportunity to grow Downtown.”

A young man tried on a suit jacket, turning to examine the fit in a mirror.

“We make people feel good about themselves with clothes,” said Mr. Michael. “People wear the clothes they purchased here and they get lots of compliments.”

A half hour later, a man in athletic gear stops by to see the store for the first time, even though he has lived Downtown for over a decade.

“If you are Downtown and ever have a fashion emergency like a button falling off, you can come to us. We will fix it for free,” Mr. Michael tells the man.

Around noon inside the white-brick restaurant in the northeast corner of Market Square, six customers sit on worn stools facing the bar. Black-and-white photos of the restaurant’s interior stare back at them, covering the mahogany wall behind the liquor bottles.

Owner Jen Grippo passes a cop a tray of crab cakes, backtracks through a hallway and turns toward the far-right corner of the restaurant’s other wing. She takes a seat at a table opposite a framed caricature of her late father holding up the restaurant’s signature fish sandwich.

“For us at the Oyster House,” she says with a glance around the 155-year-old space, “it’s business as usual.”

Outside the window behind her, a crane lifts a pile of rubble and fences surrounding the center of the plaza advertise a new Market Square — opening in 2026.

“We embrace change outside of our four walls,” Ms. Grippo says. “But within our walls, it’s all about tradition.”

Many of Market Square’s longest-standing tenants — from Original Oyster House, opened in 1870, to Nicholas Coffee, there since 1957 – pride themselves on consistency.

Around them, the square and Downtown are in flux.

Within the fenced-off area, Mascaro Construction workers are preparing to lay down new pavers — groundwork for a $14 million to $16 million overhaul of the square set to wrap up before Pittsburgh hosts the NFL Draft next spring.

Many of the businesses in Market Square were there when it was last redone in 2009 — a $5 million project that cost the square two of its businesses. At the time, Original Oyster House nearly closed, too, Ms. Grippo said.

Now, the restaurant — and many others in the square — are used to change, owners said.

“You just, as a leader, have to pivot — not panic,” Ms. Grippo says.

The center of the square is closed as construction progresses, forcing people to walk the perimeter. 

That’s why Ms. Grippo put up menus outside Original Oyster House, a move she said has brought in new business. Around mid-day, two women carrying shopping bags stop at the restaurant to scan the options.

Nicholas Coffee, a mainstay on the square’s south side, did the same — one of many adjustments owner Jordan Nicholas said he’s made to keep the doors open, even as the small shop’s wooden interior remains unchanged.

Asked how Downtown has changed over the years, Mr. Nicholas removes his glasses, rubs his forehead and looks out at the fences encircling the center of the square.

“We’ve seen so many transformations,” he says.

Construction in Market Square is on schedule; on Eighth Street, a new outdoor events venue is also set to open before the Draft, which runs from April 23 through the 25th.

“We’re not just doing this for three days,” said Jacob Machel, a director at Newmark Realty who works Downtown, owns Medi’s Market and now walks to Market Square on lunch breaks about four days a week. “Let’s do this for the next 20 years,” he adds.

Mr. Nicholas, the son of a longtime Downtown business owner, says he will never move his shop. “Downtown is the lifeblood of the city,” he says, as a line formed at his coffee bar. “If you don’t support the center of your city, the region will suffer greatly.”

Still, the Golden Triangle is “teetering” right now, he adds, with a lot of good in the works — and a lot of problems to address.

A few streets away, the building where Mr. Machel works — the K&L Gates Center — is in foreclosure, one of several historic buildings Downtown struggling with empty offices and uncertain futures.

“Downtown Pittsburgh is going through the same phases as a lot of other cities across the country,” Ms. Grippo says. “No matter how you slice it, we’re all still figuring it out — COVID really took a toll, that’s for sure.”

For her part, Ms. Grippo said she’s formed relationships with the public works employees, police officers and contractors working Downtown to understand the direction it’s headed in.

And business owners across Market Square now meet at the nearest police station once a quarter to talk about safety in the plaza. Many are part of a group chat with Pittsburgh Police Sgt. Robert Monticelli, Mr. Machel said in Medi’s Market.

In front of Primanti Brothers, a group of people with suitcases survey the square as workers in suits file out of Starbucks, families pass by and a construction worker picks up a sandwich from DiBella's Subs.

Most often, Mr. Nicholas says, visitors have the clearest view of Downtown.

“You can’t see the forest from inside the trees,” he says. “People that come here think it’s great — I think we take it for granted. We don’t realize what a gem we really have here.”

Inside Cardamone’s Salon, customers getting highlights put in their hair can watch the neighborhood go by through the massive window that looks out onto Forbes Avenue.

The glass is clean and intact now. It’s been a few weeks since two fighting teenagers smashed through the pane, but salon co-owner Josephine Sanchez remains shaken.

“I’ve always worked Downtown, but this is the worst I’ve ever seen it. This is just a sad city,” Ms. Sanchez says. “I don’t have a lot of optimism right now. My optimism is at an all-time low.”

A few weeks ago, she says, someone defecated in the doorway.

“If people are sleeping on the sidewalks and urinating up the street, it is the perfect storm for chaos,” she says.

She points to groups of kids and teenagers she says gather Downtown in the afternoons and linger into the evenings. She blames unlimited PRT bus passes that students who attend school Downtown receive. They mill around and make it hard for clients to get in and out of the salon.

She approached the mayor a few years ago, asking if the bus pass could be changed to have a limit on how late the students could stay unless they had proof of a job, but believes that her concern was brushed off.

“We are not busy in the evenings like we used to be because people just don’t want to be in the city. People don’t feel safe anymore,” she says. “I don’t know what the answer is, but it doesn’t feel like they are doing a lot to help small businesses.”

She says that while her business hasn’t been hurt from a money-making standpoint, it’s exhausting to watch what she called the Pittsburgh from her childhood “just kind of fade away.”

“It’s just sad to watch all of these little businesses that made it magical to be in the city being gone,” Ms. Sanchez said.

“I just think that it is a lot of different things that no one is addressing. I mean, we have a homeless problem. We have young children hanging out here all day. We have addicts milling around. They use the whole block as a urinal. It’s just tough.”

Steven Conboy remembers riding in the car into Downtown Pittsburgh as a kid growing up in Irwin. “Everything’s closed down a little bit earlier,” says Mr. Conboy, a 22-year-old operations intern at BNY Mellon.

He and 21-year-old Madeline Wibel had just stepped out of the heat and into Mad Chicken on Liberty Avenue this July afternoon. Ms. Wibel is from Duncansville and wasn’t familiar with Pittsburgh before this summer.

“[Pittsburgh] is almost a place I want to keep to myself and not tell everyone just how great it is,” she says. “There are little hidden gems all over the city and you wouldn’t expect a great museum to be at one corner or a very nice place to eat at another.”

Their only complaint? The twists and turns that come with trying to navigate a city amongst three rivers. It’s why Ms. Wibel prefers the bus.

Otherwise, the pair says, they have few qualms about Downtown. Mr. Conboy believes “the city’s getting cleaner,” recalling trash dotting Downtown streets back when he would take walks with his father.

“There was a lot more sidewalk activity going on and now they have cleaned up the city — I hardly see garbage anymore, because there's not a lot of homeless people around,” he says.

Mr. Conboy praises how the city has cleared up pavements, while promoting events like Picklesburgh that draw people in. “I think the city's gonna be on the up -– I don't think it's going anywhere,” he says.

Ushers in black and white begin to trickle into the Benedum Center about an hour and a half before curtain.

It’s another Wednesday, another performance night. The Pittsburgh CLO’s production of Disney’s “Frozen,” the company’s best-selling show of this year’s summer season, draws a steady stream of parents and grandparents with children, many of whom dress in princess costumes.

Men and women in business attire scurry toward parking garages, while others dressed more casually merely amble by in no particular hurry. Pittsburgh Downtown Partnership employees in yellow “Clean Team” polos pass at odd intervals, snagging bits of trash.

The streets around the Benedum aren’t busy, per se, but they’re far from empty.

On the opposite corner from the theater, a lanky man with a saxophone takes deep pulls from his water bottle, fiddling with his phone and speaker to set up the perfect background music against a cacophony of car horns and other assorted automobile noises. He begins to play with a wail of sound, improvising and bobbing the instrument in time, the occasional passerby tossing a bill into his case.

Small knots of residents sit tossing breadcrumbs to pigeons, as well as strips of some unidentifiable, gamey meat.

“Last time we visited Downtown, parking was just $7,” announces a woman who asks to be identified only by her first name, Beth.

She is waiting in the plaza with her husband and granddaughter to see “Frozen,” lamenting the increase in parking, which she says cost $35 this time.

“I’m not afraid of the big bad city, but even I have reservations walking around after dark,” the Elwood resident says. “You can’t turn on the news without hearing about a shooting somewhere around the city, it feels like.”

Shortly before 6:30 p.m., Benedum security teams line the entrance to the theater to assist elderly patrons from their cars, and people begin streaming more quickly into the hall, snapping photos of each other as they pass the  marquee.

The muffled jazz of the saxophone drifts around the corner as James Grant strolls Penn Avenue. Dressed in all black with a blue cleaning cloth draped over his right shoulder, he’s headed to his two-hour cleaning shift at the Moravia Health Office.

Mr. Grant cooks in restaurants, grills for hungry sports fans outside stadiums, and has mopped the floors of shelters, emergency rooms and nursing homes across the city.

The Pittsburgh native does not know how many jobs he’s had over his 66 years.

He just knows he likes to keep busy.

“It keeps you out of trouble and it keeps you healthy,” he said. “When I go home at night, I’ll be tired. I won’t have time to think too much.”

Mr. Grant discards trash and sweeps floors within the office’s yellow walls after workers filter out on Wednesdays and Fridays. While he enjoys the social aspect of his chaotic day shift at a kitchen in East Liberty, he savors the end-of-day quiet that comes with tidying empty rooms.

“This is a wind down,” he said, wiping his blue cloth across the vacant front desk.

Ben McClendon, Downtown manager for Pittsburgh Reliable Cleaning Services, pushes through smudged glass doors into the 810 Penn Ave. lobby at 6:20 p.m. He is paying a visit to Mr. Grant — one of the numerous check-ups on cleaning sites he conducts.

After office workers clock out, the cleaning crews clock in, shuffling into restaurants and buildings across the city every day of the week.

Before he started in April, Mr. McClendon had never considered the business of corporate space cleaning — the world of dusk-time dusting that makes it possible for office workers to plug away.

“It happens when no one is looking,” Mr. McClendon says. 

So, when the proverbial curtain pulled back to reveal rocketing demand for after-hour cleans, he was pleasantly surprised. He says they receive flurries of requests for their services each week, many centering around post-construction clean-ups, a logistical layer that’s often forgotten.

“The fast pace of the city — that’s why the demand is just so high,” he says. “Everywhere you look, something new is popping up.”

When he makes the hour-long commute Downtown from his home in Youngstown, Ohio, Mr. McClendon can’t help but notice the hustle and bustle of the city center, especially when a freshly-finished game or concert floods the sidewalks with foot traffic.

“I’m from a much smaller town,” he says. “So it’s tremendously busy up here to me.”

But the noise of passing cars and people falls away when he walks into the Moravia office and grips the hand of Mr. Grant.

For Mr. Grant, the calm of a shift at Moravia is a far cry from his four-month stint as a janitor at the Second Avenue Commons shelter two years ago.

“It wasn’t worth the money,” he says, recalling constantly cleaning up the bloody aftermath of drug activity in the showers.

Mr. Grant has been passing through Downtown for decades to get from this job to that. It’s changed a lot. 

When he was young, he says folks would have to dress up to wander the streets. “You had to act a certain way — Downtown didn’t play back in my day,” he said.

Most traces of that Downtown seem to have vanished. 

Since the pandemic, a drastic rise in the number of homeless people lining the pavements, some of them teenagers, has been hard for Mr. Grant to witness.

“I never knew the homeless were so young,” he says. “That would just catch you off guard.”

Back at the Benedum, the flow of theater patrons has slowed by the start of the 7:30 p.m. show, save for a few drips and drabs of stragglers.

The saxophone player plays a final gnarly lick before packing up his instrument and recycling his water bottle.

He crosses the street, shoulders hunched, glancing left and right, and passes his night’s earnings to a homeless veteran in a wheelchair, who clasps his hand and beams at him.

And in the gathering dusk, the musician marches off to serenade another corner.

“You hear so much about crime and homelessness, but it doesn’t really seem any different or worse than any other city,” said a man who identified himself only as John, who had gotten off work late and was heading home to Moon Township.

“I’m not sure what all the fuss is about sometimes.”

Pittsburgh Police take 10 separate reports in Downtown on this particular day, according to the National Incident-Based Reporting System. Three people are taken into custody, all on misdemeanor charges.

Two of the reported crimes are what NIBRS categorizes as “crimes against people”: a report of someone making threats shortly after 8 p.m. in Market Square and someone accused of resisting arrest on 11th Street reported shortly before 10 p.m.

Police make few physical arrests.

A man is arrested on a drug charge shortly after 1 p.m. Later, around 4:30 p.m., a man is taken into custody for alleged trespassing and destruction of property. That evening, a woman is charged with trespass and disorderly conduct.

There is no music inside the bar at the corner of Sixth and Penn at 8 p.m. — just play-by-play of the Phillies-Red Sox game on the televisions overhead.

Pittsburgh sports memorabilia from bygone times — when the Pirates were good, when the Steel Curtain was the shut-down NFL defense to beat, when Marc-Andre Fleury was still a Penguin — line the walls of Redbeard’s Sports Bar and Grill.

“We’re kind of known, much like the Warren, as a place people go to when they’re leaving their late shifts at Capital Grille or Social House, they make their way here afterwards,” says general manager Brent Kightlinger.

The late-night rush hasn’t quite started yet. Servers with black T-shirts reading, “eat, drink, watch sports,” wipe down tables. A bartender checks in on a couple scanning the menu.

Mr. Kightlinger is on the move, rushing throughout the two-floor establishment. Keys jangle from his belt loop, next to a rag tucked into his pocket and a walkie talkie clipped on his side, as he carries a tray of wings to customers.

Step outside and Downtown feels deserted.

“It’s a ghost town,” Mr. Kightlinger says. “That’s not because restaurants don’t want to stay open or people don’t want to work, but because the city isn’t set up to support nightlife.”

When Mr. Kightlinger, who is originally from Edinboro, started working at the Redbeard’s Downtown location in 2019, he said buses and the T ran nearly around the clock.

Now, T service out of Downtown stops running around 1 a.m. on weekdays and as early as 10 or 11 p.m. on Sundays. Most bus routes getting out of the area wrap up well before Redbeard’s closes at 2 a.m.

“It’s like they’re forgetting about the people who keep this city running,” Mr. Kightlinger says. “I regularly give dishwashers rides home at three or four in the morning.”

He says it doesn’t feel fair to expect employees, some who live as far as Glassport, to spend their paychecks on Ubers or expensive garage parking.

Earlier this summer, during a pogo-stick championship that brought hundreds of people to the bar, he called 911 after a few homeless people began harassing customers outside. What he got was a recorded message asking him to stay on the line because the system was overwhelmed.

“If you want to build more residences and you want to build things to bring families down here, you need to make sure those families feel safe. You feel safe when you call the police and there's a response,” he says.

During the COVID-19 pandemic, Mr. Kightlinger was forced to lay off around 20 employees who had been with the business for five or more years. While the bar has continuously produced over $2 million in sales each year since then, he has yet to see things return to pre-pandemic normalcy.

“There's been growth and there's been progress,” he says. “At the same time, we've also seen the growth of other issues, i.e. drug addiction, homelessness, and the crimes that follow.”

Mr. Kightlinger has brought up issues to local officials and has even proposed his own ideas for solutions — like a QR code system that can allow people to submit donations to shelters and housing services to curb panhandling.

“If you’re only in Downtown for your 9-5, you shouldn’t be the one making decisions that affect the late-night workers here,” he said.

It’s nearing 10 p.m. when the Frozen performance ends and patrons stream out. Most dart to their cars and zoom off as fast as traffic will allow.

Others trickle into the Warren, next door to the Benedum.

The bar fills quickly to standing room only, with visitors vying for servers’ attention and the bartenders cheerily greeting regulars by name with their favorite beverages.

“Downtown is a good time when I visit,” says Michael, a Wexford resident. “I know it’s got a reputation but I think it’s unfair, I’ve never had an issue when I come Downtown.”

(Michael also notes that he has a concealed carry permit and does occasionally carry Downtown, though he is not armed that particular night.)

As the night progresses, patrons continue to flirt, drink and game, a mix of Downtown residents and out-of-towners in for a conference or work project. The bar remains lively but without incident until closing at 2 a.m.

“Downtown is a place to work and a place to play,” said Cara Brack, a local attorney visiting the watering hole with her friend.

“But mostly, it’s a place that could be better than it is, now.”