Above an overstuffed brown leather chair, and next to a signed photo of Phil Rizzuto lighting a cigar in the toothy mouth of Yogi Berra, hangs a letter from the chambers of District Judge John Woolsey, dated January 25, 1939.

“Gentlemen,” it reads. “My son John Woolsey Jr., now at the Yale Law School, was good enough to give me a little package of your Harkness Tower Tobacco. I thought it was extraordinarily good.”

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The Owl Shop, the smoking bar on College Street where the letter hangs, feels as if it is from a time before women came to Yale, before Hitler, before Stiles and before lung cancer.

Aside from The Talking Heads’ “Psycho Killer” playing over the speakers, it’s hard to tell whether John Woolsey Jr. bought his dad Harkness Tower tobacco 70 years or three days ago.

The lounge is filled with tweed jackets, silver manes and purposeful stares. Men nod after their first puff of a new cigar as if to say, “Yes, son. You can have the good butler for the night.” The decor can be described as variations on a theme: brown.

According to Alexander Kiefhaber ’09, the people who come to The Owl Shop are “smokers, people who want to pretend they’re in the ’40s and people who can afford eight-dollar martinis.”

The wait staff at The Owl Shop knows Kiefhaber by name and drink: Lex and Ketel One Dirty Martini, respectively. They’re hard to forget — few others purposefully order a cocktail with olive juice, even fewer finish one, and virtually nobody orders a second. Kiefhaber says he is on his third. He says he goes to The Owl Shop because he wants “a little flavor of the way things used to be.”

The shop feels frozen in time. Patrons like Kiefhaber go there to relax in a dim light that seems decades away from an outside world that’s more sleek than soft. Still, The Owl Shop would probably have gone under if it hadn’t been willing to adapt to that world.

Inside the Owl Shop, it’s hard to feel nostalgic for Old Yale, because it is alive and breathing thick smoke. Unlike other bastions of Old Yale like Mory’s and J.Press, The Owl Shop has evolved and found a place in “New Yale” by being willing to innovate while remaining true to its roots.

‘If I cannot smoke cigars in heaven, then I shall not go.’

Mark Twain’s immortal words are painted on a pane of frosted glass above the 40-square-foot walk-in humidor at the back of the shop. It is a fitting epigraph for the moisture-regulated palace of tobacco behind the door — owner Glen Greenberg said he does not even know how many different cigars the bar has for sale. Its Web site lists 203 brands.

If the humidor is a palace, then employee and longtime afficionado Joe Lentine is its king. A knight in the old guard of the “nasty habit,” Lentine — known to everyone at The Owl Shop simply as “Joe” — knows that smoking causes lung cancer, but he is not bothered — he just likes to smoke.

Jay-Z boasts of his Cuban Cigars, but Lentine knows that Cuban cigars haven’t actually been worthwhile for 50 years. After the revolution in 1959, all the wealthy landowners packed up with a couple tobacco seeds and fled the country. Today, Lentine says, Dominican cigars are among the best.

As a student at Southern Connecticut College, Lentine began hanging out at The Owl Shop day and night, sampling its different tobacco blends. Eventually, the owner decided to give him a job. That was in 1964.

“I’ve never gotten away since,” Lentine said.

It’s hard to imagine Lentine as anything but a tall man with short silver hair and brown horn-rimmed glasses. He mostly spends time at the shop during the day with a select group of patrons who smoke cigars and drink whiskey at two in the afternoon. Branford College Master Steven Smith, an Owl Shop regular, put it succinctly: “Joe is New Haven.”

According to Lentine, The Owl Shop is the only commercial institution in the state at which you can still smoke and drink in the same place. It was established as both a bar and a cigar shop before there were laws prohibiting public smoking, and a grandfather clause protects it from new regulations.

It is fitting that neither the legal nor philosophical objections to smoking have sway inside The Owl Shop. Smith doesn’t consider himself a smoker, but he still smokes cigars in The Owl Shop.

After Lentine has left in the evenings, The Beatles, the Talking Heads or Parliament provide the soundtrack for drunker patrons. But during the day, Lentine keeps the XM radio tuned to the ’50s station.

“It evokes a different time — a more innocent time,” he says.

A Shop for Smokers

The Owl Shop didn’t start by selling tobacco. When Greek immigrant Joseph St. John founded the joint in 1934, it was a sort of Yale bookstore next to where Naples Pizza now stands on Wall Street. On the side, St. John mixed pipe tobacco, which gradually eclipsed textbooks, stationery and clothing as The Owl Shop’s main product.

In those days, selling blended tobacco and repairing pipes provided more than enough business to allow St. John to expand to five stores. Since then, the precious weed has been attacked as a poison, its peddlers have been painted as villains and its users have been dismissed as hopeless victims. The Owl Shop noticed these stirrings of the last quarter century, but just barely.

Yale School of Medicine professor Fred Kantor ’73 first arrived in New Haven as a resident in 1959. Back then, “[The Owl Shop] was the place in New Haven to buy tobacco,” he said. “It was a shop for smokers … I remember the owner. He was very warm, very welcoming. He spoke with an accent.”

By the time Lentine started working in 1964, The Owl Shop was one of the pre-eminent smoke shops in the country. St. John had just consolidated his five stores underneath one roof on College Street, across from the then-ritzy Schubert Theater. Stars like Helen Hayes, Alec Guinness and Vincent Price came by before and after shows. Arthur Miller was a regular.

In those days, students were allowed to smoke in Sterling Memorial Library. According to Lentine, The Owl Shop has always been “a quasi-Yale institution.” Yalies would come back from traveling the world, raving about exotic tobaccos from Europe and the Middle East only to find The Owl Shop had had them all along.

In 1964, Surgeon General William Stewart published the first of a series of reports linking smoking to lung cancer and heart disease. At the time, there were 70 million smokers in the United States. Kantor was one of those 70 million who heard the report.

“I was smoking about a pack a day, and then I just tossed them out,” he said.

He didn’t stop smoking, though — he just switched from cigarettes to cigars and pipes. Luckily, there was a store in New Haven where he could find his new goods.

But the surgeon general’s warning had an effect — eventually. It wasn’t until the ’80s that The Owl Shop patronage started to decline significantly, Lentine said.

“Everyone was concerned with the ill effects of smoking, and rightly so,” he said.

Today, anti-smoking “truth” ads are ubiquitous. Packs of cigarettes carry vague warnings. November is lung cancer awareness month. The golden days of tobacco in America and at Yale are gone, but The Owl Shop will be a home for smokers until the last tobacco plant wilts.

Even with all its history, it stands not as a relic of glory days gone by, but as a modern, viable business.

‘The Evening Crowd’

It may feel like the ’40s, but the expanded bar and seating areas in back of The Owl Shop are new as of last summer. In an effort to draw a crowd that includes more than just the regular tobacco devotees, Greenberg changed The Owl Shop from a cigar shop to a smoke lounge and bar. The Owl Shop that now draws crowds to drink, dance and smoke on Saturday nights is decidedly different than the one established in 1934.

Few would realize on a first visit that the timeless brown leather chairs in the back of the shop are less than a year old. Greenberg may have fundamentally changed the nature of his establishment, but his renovations are very carefully designed to maintain the atmosphere and ’50s feel of the original shop.

A new Owl Shop was essential, but looking like a new Owl Shop would have been damning. Greenberg said he wanted to “create an environment where people felt comfortable.”

People who like to smoke often like to drink as well. The expanded bar currently stocks 36 kinds of premium whiskey, scotch and bourbon. The brown tint matches the chairs. Fine liquor is fast becoming a fitting addition to the sophisticated, masculine charm of the shop.

In fact, every item on the menu is prefaced by the word “premium.” There aren’t a lot of “frou-frou drinks,” Greenberg says. Still, according to one waitress, customers primarily drink beer — “Amstel or Stella mostly.”

Smith said he was skeptical of the renovations at first, but he acknowledges that change has been good.

“I liked the old and seedy Owl Shop — it was like the residential colleges before renovation,” he said. “The most important thing is that [the refurbishment] brought a lot more people.”

According to Greenberg, the renovations have led to a surge in business. What Smith calls “the evening crowd” — including many Yalies — has joined the regular cigar smokers at The Owl Shop. In the lounge, these people have found a place to relax, have a drink, watch sports and smoke if they want to.

The renovated Owl Shop emphasizes comfort, socialization and drinking as much as smoking. Patrons occasionally dance in front of the bar — something that would have never have happened under St. John’s watch.

Today people play cards, chess and Chinese checkers on the tables in the back. When not in use, the games are displayed in glass cases around the store, along with a set of silver tankards and a collection of black-brown pipes against a red velvet backing. Kiefhaber has a running backgammon tournament with Amit Bhalla ’09. He refused to comment on his record.

This lounge environment is not as old as it appears, but the aged qualities are still major selling points. The Owl Shop offers a quick taste of tradition — without the price tag of a J.Press blazer.

“I love the ambience, the decorations, the old-school feel,” Nora Wessel ’10 said. “It’s authentic, whatever that means.”

Definitely Not Toad’s

While the new Owl Shop is an evening destination, it is the ultimate opposite of Toad’s or Alchemy — there aren’t a whole lot of shimmering halter tops or hats with pre-frayed brims at The Owl Shop on a Saturday night. But that may change. According to Greenberg, the renovations have brought in “all types.”

“It’s a comfortable place to go hang out with friends,” says Danny Seifert ’09, a former gymnast.

But that wasn’t always the case. Greenberg said that before the renovations, the shop was essentially “a classic cigar store.”

“There was no place to sit, [only] a small bar,” he said. “The environment wasn’t conducive to socialization.”

Greenberg tried to bring his business away from that “classic cigar store” model, but the antique ambience is still its biggest draw, despite further changes in the shop’s concept.

Six-dollar chili is currently the only item under the heading “food” in the establishment’s 11-page menu, but the new bar is about to be joined by a table serving light fare such as paninis, desserts and coffee. It’s not tobacco, but Lentine isn’t bothered.

“It will be another positive dimension,” he said while tapping his cigarette into a black ashtray on the bar.

Smith said he misses the days when The Owl Shop was more like a private club than a bar.

“I used to know all six people who would be there,” he said. “Now I don’t even go in at night. There’s a lot of noise.”

But even when The Owl Shop starts serving sandwiches, they will probably taste a little like the cigar smoke that fills the air, seeps into the walls and warms patrons’ lungs with sweet, poisonous vapor. And with characters like Lentine to anchor the establishment, The Owl Shop can’t help but remain loyal to its past.

“So long as Joe stays, it will be good,” Smith said.