Shoe pegs are ¾” long wooden “nails” that in the 19th century and

before were used in the manufacture of shoes and boots, especially to attach heels and soles.  What do they have to do with cigars? And why name your cigar after them?

    The answer lies in how a cigar is made. Cigars have rounded closed heads (the end that goes in a smoker’s mouth). The closed head requires a smoker to bite or cut the end of a cigar before he can light it and draw smoke through it. The bitten-off piece is spat onto the floor, where the small slippery lump stains the rug and otherwise annoys the woman of the house. A sloppy bite can loosen the wrapper or otherwise impair the smoking quality of the cigar.

    Clever cigarengineers have worked on solving that problem almost as long as men have smoked cigars. Tools to cut the end off were an obvious solution.  In 1868 a patent was issued for a pocket-size perforator to make a neat hole-in-the-head. Perforators and various cutting tools have been around ever since, useful gadgets for office workers or a smoker at home, but their two-handed approach to the problem was less practical for the cowboy, ditch digger or other laboring man.

    In the 1870s, cigar smoker Edward Mead patented a glass mouthpiece attached directly to each cigar, which he claimed would make it easier to hold the cigar

between the smoker’s lips and do away with the necessity of biting the end.

He didn’t address making the cigar more expensive and dangerously breakable.

No evidence exists they were ever manufactured.

    Later that decade, another entrepreneur, Joe Gross, came up with a less expensive wooden or cane mouthpiece held in place by two inches of spring wire to make
certain it didn’t break off the cigar. The wire device would have been hard on the hands and patience of the person who had to roll it into a cigar...if anyone ever did.

    Much easier was the insertion of a simple inexpensive
wooden plug … an already widely manufactured Shoe Peg … into the end of each cigar. Pull the peg and no more biting required. The idea was not patentable, and dozens, if not hundreds, of cigar makers around the U.S. and Canada adopted the novel practice. Pegged cigars, though never 1% of cigars made, became popular enough that major label printers added stock labels with that name.

       Other similar less popular innovations followed. Some time in the early-to-mid 1880s, cigar giant Straiton & Storm introduced Pinnacle cigars, patentable because they introduced a custom-shaped wooden peg into what looks in their illustration to be a pre-drilled hole in the cigar. They used the mushroom-shaped peg as a trade mark for their brand, which lasted for more than a decade.

        The Jones Brothers of Woodstock, Ontario, Canada, came up with a clever variant. Instead of an inexpensive wooden peg, they used an even cheaper strip of paper fed through the split end of their Split End Cigar, which they were able to patent in 1893. “None genuine without paper on end” warned the label. The brand was manufactured for a year or two, but how effective the paper tab is unknown.

        Although shoe pegs won the battle of clever ways to make a hole in the head by having the most factories adopt them. First used,  it appears, in the 1870s, shoe pegs were used by various makers until 1942. But the single longest-lived method used by a single maker belongs to another Canadian brand, Stonewall Jackson cigars, which for 70 years had a silk ribbon sewn through the head. Pull the ribbon out and smoke.

   Ribbons weren’t the only things sewn through the head of a cigar. This 1906 letter from a salesman to Noll Cigar Factory, contains an order for 10,000 cigars with the following instruction “each cigar is to have a red silk cord through the head of [the] cigar.” 

    This was a custom order the cigar maker appears not to have done before: “I [will] send you by mail a box so you can see what I mean.”

    The cigar maker is getting only 1¼ cents each, a seemingly low price for the cigar and threading the ribbon. That’s the wholesale price of cigars that sell for 3/5¢.

A selection of early hole-in-head peg-type boxes follows.   


Shoe Peg Cigars

and Their Many Makers

A Cigar History Museum Exclusive 

Text & Images © Tony Hyman, All rights reserved

Last addition December 13, 2012

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