What JFK and Five Other Famous Cigar Smokers Drank While They Smoked
The cigar is rarely a solo act. Across the past two centuries, every famous figure who smoked one famously also drank something with it — and the specific pairing each one chose tells us as much about the person as about the cigar.
Some of these pairings are well documented. Some are reconstructed from the writing, biographies, and habits of the people involved. All of them are revealing.
John F. Kennedy: H. Upmann Petit Coronas with Daiquiris
Kennedy's cigar of choice — H. Upmann Petit Coronas — is well known. Less well known is what he paired them with. According to Pierre Salinger, Kennedy's press secretary, the President had a marked preference for frozen daiquiris, prepared with light Cuban rum, lime juice, and sugar. The pairing isn't accidental. Both the cigar and the drink came from the same island, and Kennedy's affection for both was widely shared in the Cuban-American community he counted among his political allies.
There's a particular irony here that Kennedy himself appears to have appreciated: on February 6, 1962, the night before he signed the proclamation that initiated the Cuban embargo, Kennedy reportedly asked Salinger to acquire 1,200 Petit Coronas. He continued smoking them, with daiquiris, throughout the remainder of his presidency. A cigar and a drink that were both about to become contraband. He didn't quite live to see the supplies run out.
What it reveals: A cosmopolitan, mid-century American taste — Cuban, sophisticated, slightly indulgent — that was already becoming politically untenable in the moment Kennedy was enjoying it most.
Winston Churchill: Romeo y Julieta and La Aroma de Cuba with Champagne, Whisky, or Both
Churchill's cigars are legendary — over 250,000 smoked over his lifetime, the famous "Churchill" vitola named for him by Romeo y Julieta — but his drinking was even more determined. He was famously partial to Pol Roger champagne in the morning and afternoon, and Johnnie Walker Black Label whisky and water through the rest of the day and into the night. The cigar was constant; the drink rotated by the hour.
Churchill himself articulated the philosophy: "My rule of life prescribed as an absolutely sacred rite smoking cigars and also the drinking of alcohol before, after, and if need be during all meals and in the intervals between them." He smoked while writing speeches, while bathing, while painting watercolors at Chartwell, while at the dispatch box of the House of Commons.
What it reveals: That a cigar isn't a discrete event but a continuous companion — a rolling presence across the day's many drinks, meals, and moods. Churchill's cigar was inseparable from his work and his pleasure alike.
Ulysses S. Grant: Whatever the Era Provided, with Whisky
Grant smoked relentlessly — by some accounts, twenty cigars a day during the Civil War. He had no consistent brand loyalty in the modern sense; the cigars came as gifts from admirers, from suppliers, from constituents, in such volume after the Battle of Shiloh that his consumption habits were effectively shaped by what other people sent him. What he paired them with, however, was consistent: whisky, often a Kentucky bourbon or rye, drunk straight or with a small amount of water.
Grant's drinking was the subject of constant rumor during the Civil War — Lincoln himself reportedly said that if he could find out what brand Grant drank, he would send it to his other generals. The cigar-and-whisky combination was the working pleasure of a soldier who lived on the move, in the field, and at the writing desk. It was the pairing of duty.
Grant died in 1885 of throat cancer. He spent the final months of his life finishing his memoirs to provide for his family. He was still smoking, and still pairing them with whisky, into his final weeks.
What it reveals: A pairing born of utility rather than aesthetics — the working spirit of a working man whose pleasure was inseparable from his labor.
Mark Twain: "The Worst Cigars I Could Find" with Bourbon
Twain's pairing principles were stated clearly and repeatedly in his own writing. On cigars, he favored inexpensive, dark, strong domestic cigars — what he called "five-cent cigars" — and ridiculed the social pretension of expensive imports. On drinks, he was a committed bourbon man, with Old Crow as his stated preference for much of his adult life.
The pairing is consistent with Twain's broader literary persona: a deliberate refusal of European pretension in favor of an unembarrassed American populism. His cigars were cheap and domestic; his bourbon was Kentucky; and he wrote about both with affection and zero apology.
What it reveals: That premium pairings aren't always the interesting pairings. The combination of a strong domestic cigar with a strong domestic bourbon represents a different kind of taste — one rooted in place, in routine, and in a specifically American sense that the imported version is sometimes the lesser one.
George Burns: El Productos with Mineral Water (Mostly)
George Burns smoked for over eighty years and lived to be a hundred. He preferred El Producto cigars, an inexpensive American brand, and famously turned down offers of more expensive imports throughout his career. As for what he paired with them — Burns drank only modestly, preferring mineral water with a twist of lemon for daily smoking and reserving alcohol for special occasions, where he favored a martini.
Burns smoked roughly fifteen cigars a day until shortly before his death at 100. He was the longest-lived heavy cigar smoker on public record.
What it reveals: That cigar pairings don't have to involve alcohol. Burns's combination of cheap cigars and mineral water suggests a discipline of routine — a steady, sustainable pleasure rather than an indulgence.
Bill Clinton: Various Premium Cigars with Diet Coke
Clinton's cigars are legendary — he was a serious cigar enthusiast who appeared on the cover of Cigar Aficionado multiple times, and his post-presidency cigar habit was substantial. But the pairing he was most often photographed with wasn't bourbon or champagne. It was Diet Coke, which he drank in volume throughout his presidency and beyond.
Clinton was, for a stretch in the 1990s, more or less the public face of premium cigar enthusiasm in America — the cigar boom was peaking during his presidency, and Cigar Aficionado magazine was at its cultural high point. The Clinton-and-Diet-Coke pairing reads now as quintessentially of its era: premium cigars with mass-market American convenience, refinement and casualness combined.
What it reveals: That contemporary cigar pairing isn't bound by the conventions of the past. The pairing logic of the Pairing Wheel — complementary, balanced, contrasting — can be applied to a Diet Coke as easily as a bourbon. What matters is whether the combination works for the smoker, in the moment.
The Pattern Behind the Pairings
What strikes me about these six pairings — Kennedy's daiquiris, Churchill's champagne and whisky, Grant's bourbon, Twain's Old Crow, Burns's mineral water, Clinton's Diet Coke — is how completely they map onto the personalities they belonged to. The pairing is never a neutral choice. It's a self-portrait in miniature.
A daiquiri suggests cosmopolitan ease. A champagne suggests Edwardian command. A bourbon suggests labor and place. A mineral water suggests discipline. A Diet Coke suggests, oddly enough, accessibility — a refinement that doesn't put on airs.
This is what makes pairing interesting. It's not just chemistry, though the chemistry matters. It's a small declarative act: this goes with this, in my hands, for these reasons. The cigar is the constant; the drink is the comment.
For more on the science and craft of bourbon and cigar pairing, including the full Bourbon & Cigar Pairing Wheel and detailed pairing recommendations for thirty American distilleries, see Smoke & Oak: The Shared Legacy of Bourbon and Cigars.
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