Khyber Pass Pub on Second Street near Chestnut

If you’re a fan of Philly’s Khyber Pass Pub, you’re familiar with its vast selection of local beers and its New Orleans-inspired cuisine.

Its roots in Old City go back about a half-century — but the bar’s name is actually a reference to the Middle East.

The original Khyber Pass is a thin pathway nestled in the mountains that divide Afghanistan and Pakistan. The easiest way to travel between the two countries, it has historically been a key Asian trade route, and also a gateway for invasions into India.

So how’d the neighborhood pub get its name?

The story is an interesting three-part saga, beginning with one woman’s international love affair, continuing with her escape from an oppressive Pakistani culture, and ending with a global terrorist attack.

Khyber Pass Pub has been open for more than 40 years, and it now takes pride in its vast selection of beer and live music. Credit: Alain Quevillon / Flickr Creative Commons

The love story

Serrill Headley was an American woman who grew up on the Main Line. In the 1950s, she worked as a secretary in the Pakistani Embassy in Washington, D.C. — and that’s when she first met Sayed Salim Gilani, a Pakistani man and diplomat living in the United States.

As the story goes, the two fell in love. Together, they had an infant son, who they named Daood Sayed Gilani.

In 1960, the family of three relocated to Gilani’s home country of Pakistan. There they had another daughter, named Syedah.

But the marriage didn’t last. The issue is said to have been that while Gilani was devoted to the traditions of his homeland, Headley considered many of them oppressive to women.

The escape

So Headley fled, leaving her two children behind and returning to Philadelphia in the 1970s.

Over the next few years, she bounced around through various office jobs, and apparently dated some wealthy men. Eventually, one of them offered her enough money to open up a bar. So she opened one — and named it after the Khyber Pass.

Decorated with Afghan wedding tents and stocked with exotic beers, the tavern attracted a steady clientele, and Headley became known an area socialite.

When she finally sold the bar — to a relative of its current owners, Stephen Simons and Dave Frank (who also own Royal Boucherie, Cantina Los Caballitos, Royal Izakaya, etc.) — she claimed the name stemmed from her personal experience traipsing through the Khyber Pass on her way back to Philly.

The Khyber Pass, which connects Afghanistan and Pakistan through the mountains Credit: Alastair Nevin / Flickr Creative Commons

Forty years later, bar employees aren’t exactly sure how legit her story is.

“From everything I’ve read about her, she seemed a little dramatic,” said Amy Henderson, director of operations at Khyber Pass Pub’s current incarnation. “But that’s the truth according to what we know.”

So the story ends there, right?

“Not quite,” Henderson said. “It gets a little dicey, in that her son ended up masterminding a global terrorist plot.”

The international attack

Remember the son of Headley and Gilano, who was born in America and left behind by his mother in Pakistan? He figures into this story, too.

After being raised by his father in the Middle East, Daood Sayed Gilani — who also went by the name David Headley — returned to the U.S. at age 17 to live with his mother.

He was a conflicted dude. The New York Times described him as a young man who “once liked to get high”, had a Pakistani wife at the same time as a New York City girlfriend, and was otherwise struggling to balance his Muslim culture with his new American residence.

To try to help him, his mother put him in charge of the Khyber Pass in 1985. However, he turned out to be such a bad manager that they lost the bar entirely, and had to sell it to that relative of the current owners.

We then lose track of him for a few years — until November of 2008.

Late that month, 10 Pakistani men who were associated with a terrorist group killed 164 people in Mumbai. David Headley was accused of scouting locations at which to carry out that attack. He pleaded guilty in March of 2010, and has been locked up in a U.S. prison ever since.

The modern day

Does this story impact day-to-day life at the pub? Not really, per Henderson. When people ask how the place got its name, they answer with the tale they’ve been told — the love story and the escape, minus the terrorist part.

Every once in a while, some knowledgable folks come in who’ve already heard the full story.

“It’s difficult because every time this comes up, someone just assumes that [we’re owned by] a terrorist,” Henderson said, especially since one of the owners shares a first name with David Headley.

But the story doesn’t impact the bar’s reputation, and Henderson doesn’t think it’ll impact its future legacy, either.

“It’s become a pretty iconic place for bands to play,” she said. “When I turned 21, I knew if I wanted to see rock shows, I’d go to Khyber.” The bar, obviously, not the mountain trail.

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Michaela Winberg

Michaela Winberg is a general assignment reporter at Billy Penn. She covers LGBTQ people and culture, public spaces, and transportation and mobility. She also sometimes produces radio and web features...