Revival of the Fittest

Bill Paley breathes life back into his original family legacy.

Cigars are William C. Paley’s birthright, but he had no idea just how deeply they ran in his family.

In the 1920s, Paley’s father, William S. Paley, sold his shares in his own father’s cigar company—La Palina—to buy seven radio stations that eventually became the CBS radio and television networks, which made William S. Paley—and, later, William C. Paley—wealthy men.

Bad blood between Paley’s father and grandfather may have lingered for decades— or perhaps it was merely the passage of time.

“Nobody ever talked about La Palina when I was growing up,” says Paley, now 67. “It was in the past.”

Unlike his famous father and grandfather, Sam, a Ukrainian immigrant who founded the La Palina cigar company in the 1800s, William C. Paley came to cigars late in life, when he realized the critical role they had played in his family’s fortunes.

Paley had dropped out of college, went to Vietnam, where he made films for the Army, lived on a sailboat, got into the restaurant business, struggled with addiction, then became an addiction counselor himself.

While sailing around the Bahamas in the late 1980s and 1990s while in his 40s, Paley became infatuated with Cuban cigars.

“I loved them, and I got fascinated,” Paley says during an interview at Moana Surfrider as he admired one of his own, modern versions of the La Palina brand that has gained a following in HawaiÊ»i. “I would make periodic trips to Havana to visit the cigar factories and just got enamored with the whole allure of it. It’s extraordinary.”

So is the story of how a 20th-century American media empire emerged from a 19th-century cigar company—and how a third generation cigar maker resurrected his family’s brand from obscurity:

Sam Paley came to the New World as a boy, sometime around the 1870s, and got a job reading newspapers and novels to the immigrant workers in a Chicago cigar factory.

“He was what they call a ‘lector,’ and his job was to keep them entertained while they were rolling [cigars],” Paley says. “If you look at the names of the great cigar lines—Montecristo, Romeo y Julieta, Sancho Panza—they all were named after characters in great novels because that’s what was read to them.”


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La Palina's El Diario is "a richly flavored medium-bodied cigar" (photo courtesy La Palina Cigars).

Sam went from reading out loud to learning his craft, became a master blender and opened his own factory, Congress Cigars, in 1896, while still in his 20s.

“It wasn’t in his blood, but it became in his blood,” Paley says. “By 1910, they were producing more than 1 million cigars per day in various factories. Th ey were cheap, 5-cent cigars, but they were particularly good.”

Sam moved operations to Philadelphia in the 1920s but kept several regional factories to meet the demand for freshly rolled cigars.

And he renamed the company “La Palina,” after the name the cigar makers used for Sam’s wife, Goldie.

“When my grandmother would come into the factory, instead of saying, ‘Mrs. Paley,’ they called her ‘La Palina’ for Paley. Paley’s a Russian name, and they had Latinized it.”

Th e logo, for both the old cigars and the new ones that Paley now makes, also features a Latinized photo of Paley’s grandmother.

“She is La Palina,” Paley says. “I found the original lithographs for the original labeling that was copyrighted in 1896. My grandfather had a picture of a woman who was originally intended to be my grandmother. She was too modest, so it turned into being more of a Latin lady.”

William S. Paley joined his father’s business in the 1920s, after graduating from Wharton Business School, and took over advertising and marketing. He soon produced a radio show called “La Palina Hour” that became a hit but angered his father.

“My grandfather was appalled that my father had spent $100 on a radio show,” Paley says. “For the whole series, that was very inexpensive. But my grandfather didn’t like this and shut down the show.”

But cigar sales had doubled. “People were stopping my grandfather on the street saying, ‘Sam, what happened to the show?,'” Paley says. “Nobody had ever advertised a cigar on radio. But my father understood the value of the medium. My grandfather was a scientist. My father was a marketer.”

William S. Paley then sold his shares in La Palina and invested in radio stations that included United Independent Broadcasters, which Paley renamed Columbia Broadcasting System. He was 28.

Soon after, in the early 1930s, Sam sold his cigar company, which changed hands and names over the decades that followed. Eventually, in the 1960s, the La Palina brand disappeared.

“In the ’60s, that’s the last you’ll see of La Palina,” Paley says. “It just sort of faded out.”

When his father died in 1989, Paley bought his dad’s Nassau estate in the Bahamas and planned to offer rich clients a first-class rental home—complete with a full staff, gourmet chef and house brand cigar.

But because of Bahamian duty fees, the price of Cuban cigars became prohibitive.

So when Paley smoked a Dominican-made cigar in the Bahamas, “I was blown away,” and his quest to make his own brand began.

He enlisted the services of Avelino Lara, “one of Castro’s right-hand people,” who helped Paley blend leaves from Costa Rica, Honduras, Nicaragua and Ecuador at a Bahamian cigar factory.

Paley wanted to capture the smooth, sweet taste of Cuban cigars, which changed intensity as they were smoked.

“I brought it back to the states and asked people in the cigar business I respected, ‘What’s wrong with it?,'” Paley says. “Everyone liked it. They said it needed to be rolled a little tighter, but there was no question about the blend. Th at was the first step in me learning to trust my own palate. I wanted to make what I liked. It was the family attitude: If you trust your gut, other people will like it, too.”

In 2008, Paley spent $5,000 to buy the La Palina name from a company that collects unused trademarks.

“It was my heritage,” Paley says. But like his father, Paley also saw marketing potential.

“Reinvigorating an old family line is an irresistible story,” he says. “It’s part of a great American success story, and I realized people would want to hear that. At the same time, it gave me the authority as a cigar maker.”

He then went on a search for the best cigar makers, factories and leaves from the Dominican Republic, Ecuador and Nicaragua.

Today, Paley’s cigars come out of factories in the Dominican Republic, Honduras and Miami’s Little Havana section. In Miami, the limited “Goldie” line, named after his grandmother, is produced in a cigar factory called El Titan de Bronze, which is owned by a woman.

Inside El Titan de Bronze, all 25,000 Goldies are hand-rolled each year by only one person, the legendary Maria Sierra, “the first woman hired by Castro to work in a Cuban cigar factory,” Paley says. “She rolled for Castro around the world. In Miami, I have a cigar named after a woman, made in a factory owned by a woman and rolled by a woman. I consider this a testament to women in the cigar industry in a male-dominated industry.”

Christopher Maxwell, who owns the chain of Tobaccos of Hawaii stores that carries the La Palina cigar line, was unaware of Paley’s family history.

Maxwell only knew that Paley turns out cigars that get rave reviews.

“It’s a mediumto full-body cigar with really rich complex flavors,” Maxwell says. “Th ey’re sort of a unique cigar that I wouldn’t compare to anything. It’s a good cigar, and it does well for us and that’s the main thing. As a wise man once old me, ‘Sell what sells—not what you like.'”

Mike Sato, one of the buyers for Tamura’s Fine Wines & Liquors locations that carry Paley’s cigars, called La Palina: “a very boutique brand that has a pretty big following among cigar enthusiasts.”

Personally, Sato prefers La Palina’s “Kill Bill,” which retails for $9.

“Th ey’ve received numerous 90-plus gradings, and they get a lot of really good reviews,” Sato says. “Th eir cigars are more toward the mild to medium, medium-plus side, which is good for casual smokers, beginner smokers. For the quality, the prices are fantastic.”

Like Maxwell, Sato believes Paley’s family history plays little role in the appeal for La Palina cigars in HawaiÊ»i.

“The product has to stand up,” Sato says. “I’m definitely looking for a quality product.”

But Paley could not be happier that La Palina has found new life as a Paley-owned business.

“I don’t need the money,” Paley says. “I am a wealthy man. But I am passionate about this. I wanted to be the third generation of successful Paleys who love cigars. As I grew older, I realized that’s the essence of life, to keep engaged. And this is something I’ve really gotten engaged in.”

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