[Illustrations by ALEX FINE]
DAN GROSS: No deal has been reached, but we hear “Real World: Los Angeles” cast mate Glen Naessens and his brother Mike, who owns Eulogy (136 Chestnut), are trying to buy the Khyber (56 S. 2nd), which is mere feet away. Rumors of the Old City rock club being for sale have swirled for about a year, but nothing has come to fruition. Khyber co-owner Stephen Simons declined to comment yesterday. Simons owns the building and co-owns the bar with Dave Frank. The pair also operate the Royal Tavern, Cantina Los Caballitos and Cantina Dos Segundos. MORE
RELATED: David Coleman Headley’s mother, Serrill Headley, founded Old City’s Khyber Pass (now just known as the Khyber) back in the ’70s. As a teenager, Headley lived above the bar and he would eventually manage it for his mother. He would later go on to become a video-store entrepreneur, international drug smuggler, and, after getting caught with two kilos of heroin, he bacame an informant for the DEA, according to the Inquirer. He would also earn the grim distinction of being the American jihadist with the highest body count. Much has been written about Headley, especially in India, where he is regarded as Public Enemy No. 1, but for all we have learned, he remains something of a cipher, quite literally an international man of mystery. Headley was born Daood Gilani in 1960 in Washington, D.C. His mother, who died in 2008, grew up in Bryn Mawr and ran away from home when she was 15, eventually settling in the nation’s capital and finding work as a secretary, according to the Inquirer.
“She was very independent, very freewheeling,” says her brother, William Headley, who owns a day-care center in Nottingham, Pa. 
It was in D.C. that Serrill met and eventually married Pakistani diplomat Syed Saleem Gilani. “He was very charming and distinguished,” William says. “He swept her off her feet.” Shortly after Daood was born, the family moved to Karachi, Pakistan. But Serrill, whom her brother characterizes as a proto-feminist, soon chafed under the chauvinism of Pakistani society.
“She told me that Daood’s father had hit her,” says Lisa Sloat, a veteran bartender in the Philadelphia restaurant scene who interviewed Serrill for a bar guide she used to publish in the early ’90s. “She told me she left him and escaped through the Khyber Pass to Afghanistan. That’s why she named the bar Khyber Pass.”
Serrill eventually returned to Philadelphia—without Daood (“In Pakistan, men own the children,” she was quoted as saying at the time. “There are no rights for women.”)—and in 1973 she enrolled in bartending school. “She was a stunner, snow-white skin,” recalls Ronnie Horsman, 85, who ran the Philadelphia Bartending School. “After she took the course she told me she was going to buy a bar on Second Street. I told her ‘Hold on, you should try this out first and see if you like it’ but she had her mind set.”
And so the Khyber Pass was born. Serrill decorated the joint with exotic accents, like the hide of a Bengal tiger that once killed a man on the Ganges and an oversized portrait of Queen Victoria. She covered up the water-damaged ceiling with tented fabric, mounting hand-painted camel skin lamps onto the bar and knocking out two holes in the wall to create a music-performance space next door. She also offered customers an extensive selection of beers, stocking the cooler with nearly 200 brands from around the world. “That was unheard of at the time, this was way before the craft-beer revolution,” Sloat says. She opened the city’s first wine bar upstairs. Year after year, the Khyber Pass would be voted Best Pub, Best Jukebox and Best Live Music Venue in readers’ polls. […] By 1987, hobbled by health issues and business difficulties, Serrill put the bar up for sale. It was eventually purchased by the Simons family. Brothers Steve and Dave Simons assumed management duties and the Khyber re-opened in the fall of 1988. Under their stewardship, the Khyber would become a local mecca of indie-rock with a national rep among touring bands as the place to play in Philadelphia. MORE