Cigar Aficionado

A Smoky Derby Day

Yesterday was a picture-perfect Derby Day, and my wife and I attended a local party with about four dozen other couples, dressed in our derby finest. It was a top-notch affair, complete with a Dixie band playing Southern favorites, country ham on homemade biscuits and honey-dipped fried chicken, and maybe just a few too many mint juleps made with sour mash bourbon.

And yeah, there were cigars.

Few of my friends have cigar-friendly homes—mine is a rarity—but this outdoor party meant cigars were almost as common as the ornate hats worn by nearly every lady in attendance.

Our host had a box of Padrón 2000 Maduros open on a table next to the bar, plus a box of private-label Connecticut-shade Churchills for those who preferred a very mild smoke. Before I could take one of the Padróns, my buddy Jeff handed me a Montecristo No. 4 brought back from a recent international trip. He was paying me back for a cigar I had given him a few weeks ago.

I lit up the slightly dry Monte, took a puff, and then took a swig of the mint julep. The cigar was lovely, with an appealing oaky wood character and a touch of leather. I smoked and enjoyed the crisp breeze as a scattering of dogwood blooms fluttered in the air.

I was about halfway done with the Montecristo as the party was getting into full swing. After the band played My Kentucky Home, host Jay stood in front of the crowd and auctioned off the Derby horses: the money for the horses went into a pot, most of which would go to the owner of the No. 1 horse. (Second place was worth $200; third place $100.) I joined a consortium with my friends Mark and Tim. We had plenty of confidence, despite our near-complete lack of horse racing knowledge, and our inability to name even one horse running in the race. We quickly consulted a betting page and felt a little better about our chances.

The bidding was furious for early favorite Curlin, but Mark had a good feeling about another horse, Street Sense, who started off at 10-1 but was down to 7-1 when we were doing the auction. Bidding began on Street Sense: Twenty bucks, then $40, then soon it was $80, pretty pricey for this particular contest. We were in at $110 when another bid came in at $120. Mark raised his hand for $130, but it was too late. We had missed Street Sense. No problem—we took Scat Daddy in a later round. I took a final drag on the Montecristo and headed into the house to watch the race.

You know what happened. Street Sense won. Scat Daddy? More scat this day than daddy. He was a no show. So close to glory! The triumvirate soothed its bruised egos with generous doses of Knob Creek, poured from Jay’s quite impressive basement bar.

Soon we were back outside, ready for cigar No. 2, the Padrón 2000. Lots of cocoa flavors, with a sweet, rich finish. It was a truly great cigar. Did it make me entirely forget that I could have won $500 if we had acted just a touch quicker on Street Sense? No. But I wasn’t complaining. After the cigar, plus a few more stiff drinks, I didn’t feel quite as bad.