Memoirs: Of Habanos and Varadero

My journey with the Leaf began in my youth in the disadvantaged neighborhoods of inner-city Toronto. It was in my sixteenth year that I asked my mother for a tobacco-pipe for Christmas. Despite the fact that my parents were non-smokers, and I was also underage I awoke on Christmas morn to an unsubtly wrapped, pipe-shaped gift under the tree, with an accompanying pouch of cherry Cavendish. I smoked that pipe for many a year (and not always tobacco in it if you catch my drift). I was however probably the only one in the hood buying Century Sam’s and Phillies Blunts with the intention of smoking them…To think I used to smoke American cigars…Surely a mistake of youth and inexperience, but to a poor kid like me, Cuban’s were just a mythical status symbol.

I grew up and moved up from the Jane St. set to the Bay St. set. It was in my twenty-fifth year that I smoked my first Cuban. I was working for a Wall St. investment bank at the time where my directors were all Americans. They knew I smoked and I was often conscripted to go to the lavish downtown B&M to grab Cuban’s which were easily and routinely smuggled across the border (Even after 9/11; banksters, it seems, were still treated differently than the plebs.). I got a ‘grab something for yourself’ one time along with a fat wad of cash and they rest was history. Suffice it to say I haven’t smoked an American cigar since…

I used to go to the B&M to gawk and drool in the walk-in humidor only to walk-out with a ‘special occasion’ tubo and a trusty 5 pack of JLP’s. Perhaps it was my start with American’s that had me into Piedra’s; they were the most popular brand in America pre-embargo, but I digress…I suffered through many a year of egregious Canadian taxes, only buying what I was smoking day-to-day, nary a humidor in sight. It was in my thirtieth year that I married a women who’s only major flaw was hating the smell of cigar smoke. Not too long after was a wee-one and the responsibility of a new family had me rethinking my habit. The shrewd business man in me approached the task from a fiscal angle. I needed to cut out the middle-man, and the tax-man for that matter, I needed to go to the source…

I found that my wife had a fondness for travel, and soon I was steering her toward Cuba. She was easily persuaded, just point her in the direction of the beach and she could care less about cost-benefit analyses and ethereal ‘cigar savings’ offsetting the ultra-cheap deals out of Pearson. I can still remember my first haul. Suffice it to say that I haven’t shopped at a B&M since…

I am about to return to the Motherland for the third-time in three-years, in three days. It will be the first time however that the little one will be staying behind with the grand-folks.  Ostensibly it is to celebrate our fifth anniversary; but my wife allows me my little subterfuges. As long as I am there, however there is no harm in indulging in a few of my many passions; fine-cigars, white-rum, and seaside-golf…

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