Race to the Roses – Five Days. Five Samplers. Win Pappy. The Kentucky Derby is days away. And starting Monday, April 27th, we're running our own race.
Each day leading up to race day, Tobacconist of Greenwich drops one exclusive premium cigar sampler. Five samplers. Five days. Each one is a curated flight from some of the most respected names in the world of premium tobacco — La Flor Dominicana, God of Fire, Arturo Fuente, Drew Estate, Padrón, Plasencia. And each one is a horse in our race.
How the Race Works
At the end of the five days, the sampler that sold the most units wins the race. Every customer who purchased the winning sampler is automatically entered into a raffle for the grand prize: a bottle of Pappy Van Winkle Old Rip Van Winkle 10 Year — a bourbon worth $800+ and worth racing for.
You can back one horse. You can back two. You can back all five — and if you do, you're in the pot regardless of which sampler wins the race. The more you back, the better your odds.
The Mechanics
The mechanic rewards both loyalty and strategy. Purchase one sampler and you're entered into that horse's pool — if it wins, your name goes into the draw. Purchase multiple samplers and you're entered into multiple pools, increasing your chances. Purchase all five and your entry is guaranteed regardless of outcome. There's no wrong move, but there is a hedge: back the whole field.
The Horses
Five samplers. Five horses. One drops each day at 2:00 PM ET.
#1 Commandment — Monday, April 27
#2 Further Ado — Tuesday, April 28
#3 Renegade — Wednesday, April 29
#4 So Happy — Thursday, April 30
#5 Fulleffort — Friday, May 1
The Cigars
Every sampler is built from the top shelf. These are not cigars packaged to hit a price point. These are allocated, limited, and highly sought-after releases — assembled into five distinct flights, each with its own character.
La Flor Dominicana Rare Finds appears in all five samplers — not by coincidence. A cigar that earns its name every time you light one, the Rare Finds program represents Litto Gomez's most experimental and limited work, produced in small batches and released without warning.
God of Fire brings five of the line's most celebrated expressions across the samplers: the Don Carlos Toro, one of the more well-rounded God of Fire cigars; the Carlito Double Robusto, the boldest of all God of Fire cigars; the Serie Aniversario 60, a blend conceived to honor sixty years of the Fuente family in tobacco and built to stand as a measure of everything that legacy represents; the Serie B Diadema, a large-format cigar renowned for its sophisticated blend of aged Dominican tobaccos; and the Don Carlos Double Robusto Tubo in the gold tube, a cigar made to honor Don Carlos Fuente Sr. and constructed to be worthy of that responsibility.
Arturo Fuente contributes selections from across their most sought-after lines: the Opus X Super Belicoso, grown on a single estate in the Dominican Republic and released on a schedule that answers to no one but the tobacco; the Opus X XXX Belicoso, the legendary full-bodied expression of Opus X; the Añejo Shark, aged in cognac barrels, a cigar whose finish reveals itself slowly and without apology; the Angel's Share Reserva D'Chateau, a rare offshoot of the iconic Opus X line with the legendary Dominican Rosado wrapper — the vitola that gives this tobacco the full length of time it wants, and asks you to do the same; and the Casa Fuente Robusto, originally produced for the lounge that bears the family's name in Las Vegas and rarely found beyond those walls.
Drew Estate delivers the Liga Privada No. 9 Belicoso — the cigar that defined what the Liga name would come to mean — and the Liga Privada T52 Belicoso, darker and more deliberate than the No. 9 and every bit its equal.
Padrón adds the 1964 Toro Maduro, a blend that has quietly set the standard for an entire generation of premium cigars, and the Black PB 99 Maduro — a single stick in Sampler #4, chosen because when a cigar is that precise, that resolved, a single example is the appropriate introduction.
Plasencia rounds out the opening flight with the Alma Fuerte Claro Eduardo, from one of Nicaragua's most storied growing families.
The Stakes
One sampler — Entry in one pool. If your horse wins, you're in the draw.
Two to four samplers — Entries in multiple pools. More horses, better odds.
All five samplers — Guaranteed entry. You're in the draw no matter which horse wins.
The Prize
The winner of the raffle receives a bottle of Pappy Van Winkle Old Rip Van Winkle 10 Year — a bourbon that needs no introduction. Valued at $800+, it's a bottle worthy of the Run for the Roses.
The Timeline
Sales open Monday, April 27 at 2:00 PM ET with the first sampler drop. A new horse enters the race each day at the same time. Sales close at midnight on Friday, May 1. The winning sampler is declared on Race Day — Saturday, May 2 — and the raffle winner is announced shortly after.
Five horses. Five days. One race. One bottle worth winning.
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