At 52, Jack Tar has let himself go. His paint, once vibrant Monaco blue, has faded to a pastel dusk. His roof leaks. His pool lies empty and stained.

In the 1960s, when Jack Tar and his 100 rooms were built, the motel was considered the peak of modernity. With a rooftop swimming pool, parking garage and a restaurant, he wooed travelers with the promise: “Prepare to be pampered.”

But the years have been unkind to Jack Tar. Criticsmostly newcomers and out-of-townershave called him an architectural blemish in downtown that needs to be razed. Yet, many Durham residents have warmed to his Mid-Century Modern facade, the long glass windows, split-levels and minimalist lines. They have come to embrace the motel, nicknamed the Oprah Building after former owner Ronnie Sturdivant splashed “We Want Oprah,” his cri de coeur, across the second-story windows.

Over time, the Jack Tar has become a distinct part of Durham’s sense of place. But that sense of place is changing. From the top of the motel parking garage is a 270-degree view of Durham’s renaissancetech start-ups, boutique hotels, art galleries and nationally renowned restaurantsthat has excluded the Jack Tar. The city’s new energy has also left behind the dozens of transients, the disabled and the down-and-out who, over the past 10-plus years, have lived at the Jack Tar illegally.

Those residents, plus Blue Coffee Cafe and the other businesses tucked inside the motel will have to leave no later than early next year. That’s when Austin Lawrence Partners, the Aspen, Colo., company that bought the Jack Tar from the Sturdivant family for $5 million last month, will begin to restore him to his former glory.

When renovations are completed in 2016, Greg Hills, founder and managing partner of Austin Lawrence, expects the Jack Tar will be reimagined as boutique hotel. Inspired in part by the Standard on Sunset Boulevard in Hollywood, it will feature 74 mid-priced rooms with a restaurant and stores on the ground floor. The top floor will sport a bar and lounge, open to the public.

“[The Jack Tar] has been so maligned,” says architect Scott Harmon, whom Austin Lawrence hired to do the motel’s redesign. “Its history has the hilarity and poignancy of a Southern Gothic novel.”

Few people venture above the second floor. Here, a half-dozen people still live at the Jack Tar, not including the squatters who break into some of the vacant units by pushing the air conditioners through the window, and then nap on the mattresses stored inside. On temporary leases, tenants paid the Sturdivants, who, until recently owned the building, as much as $500 a month for tiny rooms that did not meet minimum rental housing code. The rooms are not listed in the classified ads or on Craigslist; people wind up here through word-of-mouth, when they don’t have enough money for a deposit or utilities. Or when they just want to be left alone.

“That’s one nice thing about it,” says a former tenant. “No one bothers you.”

To get up into the old Jack Tar, either ride a creaky elevator or enter through the parking garage and ascend several dim, urine-scented stairwells to the third and fourth floors. A glass doorwith “The Upper Deck” etched in elegant script on the windowleads to the fourth floor. From there, the pool and rooms reveal the decline of a motel whose 1960s brochures promised so much luxury.

“The mold room,” as the tenants call it, is on the fourth floor. The name is self-explanatory. Inside, the ceiling has caved in on a recliner. A lamp without a bulb or a shade stands nearby. A bed, desks, mattresses, a bookshelf and the floor are covered in dust, chipped paint and garbage.

Down the hall is “the bird room,” named for the winged invaders that have shit on the floor.

Wooden 4-by-10 poles support part of the sagging overhang. The steps into the pool felt as pliable as a sponge. The rooms are about the size of those at a Motel 6, and do not include stoves or refrigerators. A former tenant says residents didn’t have hot water for five months, even though the Sturdivants were responsible for paying the utilities.

“We complain. They don’t do nothing,” the tenant says of the Sturdivants, one of whom lives on the second floor, reportedly with a stove, refrigerator and other amenities not provided to the tenants.

Contacted at their leasing office, the Sturdivants did not respond to calls from the INDY.

That people live at the Jack Tar is one of downtown’s worst-kept secrets. The city’s Neighborhood Improvement Services department, which is in charge of inspecting rental properties, told the INDY it did not know anyone lived at the motel. However, people have rented rooms there for at least 10 years, according to tenants.

In January, Durham police responded to a call concerning a tenant who had smashed his fourth-floor window and hurled many of his belongings onto the street. His shoes, clothing and shards of glass landed in front of Blue Coffee Cafe, which occupies the ground floor of the Jack Tar, at one of the busiest intersections in the city.

The building conditions should not surprise city officials. The Sturdivant family is notorious in Durham for neglecting their properties. Ronnie Sturdivant ran a flophouse in an old Holiday Inn at Vickers Avenue and West Chapel Hill Street. He called it Temporary Quarters. City Councilman Eugene Brown, whose realty office was across the street, called it “Permanent Disaster.”

In 1998, a judge, on the recommendation of the county health department, shut it down.

“Now the developer has inherited the Sturdivants’ problem at the Jack Tar,” Brown told the INDY. “It’s unfortunate.”

According to Neighborhood Improvement Services, if tenants are to remain at the Jack Tar through October, Austin Lawrence Partners will be required to bring the property up to housing code.

Hills says a notice is scheduled to go out this week informing residents they need to find another place to live as soon as possible. “There is a safety issue with the residential folks, and we prefer no one lives there,” Hills says.

Update, July 30: After press time on Tuesday evening, a tenant told the INDY that he had received a notice to vacate no later than two weeks.

The Jack Tar was built in the 200 block of Corcoran Street in 1962 by the Homeland Investment Company, whose motto was “Improving Downtown Durham” (certainly more straight-laced than the city’s recent tagline “Find Your Inner Cool.”)

The motel served as an extensionliterally, since there was a skywalkof the Washington Duke Hotel, a stately neoclassical building across the street, where CCB Plaza and Major the Bulla bronze sculpture emblematic of the city’s nicknameare now.

But the Washington Duke had “no parking or pool,” says Gary Kueber, who runs the Open Durham blog. “And the motel was built to provide those amenities.”

In 1966, the Jack Tar expanded to consume the entire block, taking out several old buildings in the process. Within 10 years, the Washington Duke hotel was demolished; the Jack Tar closed in 1977.

In 1980, Homeland sold the motel to DFH Properties, which leased the space. In 1995, property deeds show DFH sold the Jack Tar to Ronnie Sturdivant. By then, the motel was considered kitchsy and permanently out of style.

“When I first writing about architecture in Durham, I was not a fan,” Kueber says. “I viewed it as ugly, and asked why this had taken place of early 20th century buildings that used to be there.”

Eventually, like many Durhamites, Kueber came around. By 2011, the Jack Tar was considered endangered by Preservation Durham, which listed it among the city’s Places in Peril. In 2012, Roger Perry of East West Partners in Chapel Hillthe company building apartments on the Liberty Warehouse siteconsidered buying and razing the property, but he could not settle on a price with the Sturdivants.

“It would have been a mistake to tear it down,” Harmon, the architect hired by Austin Lawrence, Partners says.

Scott Bednaz, who developed the historic Straw Valley property in southwest Durham, says he offered the Sturdivants $2.5 million in cash for the Jack Tar.

Bednaz envisioned renovating the existing building for startups, small businesses, restaurants and retail. He would have built new condos on the upper levels and extended the motel by several floors. After an initial conversation, the Sturdivants did not return his calls, Bednaz says.

Then Austin Lawrence Partners struck a deal for the property, whose taxable value was assessed by the county tax office at $1.9 million.

“We’re thrilled that something could happen to save it,” says Wendy Hillis, executive director of Preservation Durham. “There’s definitely a market for it.”

The Jack Tar was an afterthought to the larger City Center Project, a 26-story tower holding 101 apartments and 31 condos, plus office space and two stories of underground parking, at a vacant lot at Corcoran and Parrish streets.

But like the original builders of the Jack Tar, Hills needs the motel for parking. Of the Jack Tar’s 250 spaces, 50 will be reserved for the public, although those spaces could free up on nights and weekends.

“It’s a peculiar-looking building, but it’s grown on me,” says Hills, who is also renovating several decrepit buildings along West Parrish and West Main streets.

Estimated cost to renovate the motel is $20 million. Some of that will be offset by state and federal tax credits, since the motel is listed as a contributing structure to the downtown historic district.

The rooms will be modern and “minimalist,” and cater to a younger crowd looking for an affordable motel, more in line with the Marriott, which lists its nightly rate at $159.

Adjacent to the Jack Tar, two hotels are under construction, raising practical questions of whether downtown can handle another. The 21c Museum Hotel is scheduled to open early next year with 124 rooms. Hotel Durham in the old Mutual Savings Bank building on East Chapel Hill Street will have 54 rooms and a rooftop bar.

Shelly Green of the Durham Convention & Visitors Bureau told City Council this spring that the economic and tourism demand could accommodate 1,200 rooms.

On a recent morning at Blue Coffee Cafe, which occupies part of the ground floor of the Jack Tar, about a dozen patrons chatted or worked on their computers.

One of downtown’s prominent African-American-owned businesses, Blue Coffee has anchored this corner for nine years. It is culturally and politically significant: Barack Obama and Joe Biden stopped by during their 2008 campaign. State and local lawmakers debrief their constituents here.

But the cafe will have to leave, at least temporarily, when construction begins in January. After the motel renovations are finished, the cafe will become part of the motel lobby. Nonetheless, says owner Gwen Matthews, “I want to come back.”

Hills and Matthews have discussed that prospect. Its feasibility hinges on the rent, which Hill says will be competitive with other downtown commercial space: “You want to balance affordability and a fair return on your investment. And the businesses have to be good for the city.”

The motel’s directory lists a dozen businessescab services, a youth mentorship programbut most of the first two floors are vacant. The overhead lighting is jaundiced. The hallways smell stale, as if the air has not been exchanged since 1970. On the second floor, several ceiling tiles have caved in, and water drips into a metal buffet pan. Down the hall is the office of Referrals Roofing.

Last week, a pickup truck parked out front, its bed filled with office equipment. That evening, a storm brewed in the west, and as the wind kicked up, two residents left their rooms, stood on the balcony and watched it roll in.