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by Michael Austin | Photo: Frank Gaglione/Getty Images | Men's Book Chicago magazine | March 4, 2013

The Monopoly man knew it, and so did Winston Churchill. Fidel Castro and Jay-Z know it, too. They all know that a high-quality cigar is the ultimate celebration of the good life. It just doesn’t get much better than when you’ve got a premium stogie in your mouth or between your fingers at the end of the day.

“There are always people who have money and they want what they want,” says Rhoda Bogardus, the buyer and manager at Hubbard State Cigar (6 W. Hubbard St., 312.670.0687).“We’ve seen no downturn in expensive cigars. I was always embarrassed to bring the expensive cigars out and put them in the case, but not anymore.”

Generally speaking, an expensive cigar is anything more than $15. At Hubbard State Cigar, that includes many offerings from Davidoff—widely regarded as the Mercedes of cigar brands. Bogardus recommends the Davidoff Anniversario #3, which is a medium- to full-bodied cigar, and sells for $20 per stick (that’s cigar slang for “each”). Another coveted offering from Hubbard State is the Padron Family Reserve, which was made for Jorge Padron’s 85th birthday. These sell for $29 each and were released in June of 2012.

The cigar Bogardus recommends most enthusiastically, though, is the Arturo Fuente Opus X Lost City. And it has to have the coolest story of any cigar on the market today. As the story goes, in the mid-2000s Andy Garcia was directing and starring in a movie called The Lost City, which was being shot in the Dominican Republic. It was the offseason for tobacco and the fields were bare. For authenticity’s sake Garcia hired a cigar company to plant a special crop, just for the filming. The company later harvested the crop and started making cigars out of it. Soon they realized that the crop was incredible.

Thus, Opus X Lost City cigars were born, and they are for sale at Hubbard State for $37 each. The store gets two shipments of them a year, and only four to six boxes per shipment (each box containing 10 cigars). They arrive around Christmas and then again in May or June, so mark your calendar. Both the Padron and the Opus X are on the full-bodied side, complex and smooth with a wrapper that is rich and oily, says Bogardus.

Sean Brown, a tobacconist at Up Down Cigar in Old Town (1550 N. Wells St., 312.337.8025, updowncigar.com), says the standard Opus X, made by Arturo Fuente, is popular with the Hollywood crowd, and has been a status symbol cigar since the 1990s when it came out as the first puro outside of Cuba (meaning all of the tobacco in the cigar comes from the same country). Since then, celebrities and general players have had no problem plunking down the required dough for such a smoke ($75 for a pack of two at Up Down Cigar).

Up Down also carries Cohiba limited-edition cigars for $30 and up, but for anyone who really wants to burn through some cash, Up Down offers Partagás 150s for $60 a stick. The Partagás 150s are very rare, and more than 10 years old (stored in perfect humidor conditions to preserve them), so if you want to stock up, the box of 100 is yours for a cool $6,000.

“People come in to our store all the time looking for the cigar that Jay-Z smokes,” says Adam Johnson of Iwan Ries (19 S. Wabash Ave., second floor, 312.372.1306, iwanries.com), the country’s oldest family-owned tobacco shop. Iwan Ries doesn’t carry that cigar, the Zino Platinum, made by Davidoff, but it does carry other cigars by Davidoff, including the Millennium Churchill ($26), the Double R ($27) and the Anniversario #1 ($36).

“Men are out having a few drinks and they want a nice cigar,” says Bogardus, of Hubbard State. “Or they want to say thank you to someone who’s done them a special favor—so that’s when they want that cigar that might be a little on the pricier side. It’s like buying a diamond. It only hurts the first time.”