Image via Wikipedia

In my newest joint venture we sent out an email in which I wrote, “We did a conference call to a guy I consider to be pretty well healed.” It turned out that I was understood in what I meant by “well healed” but that I had written it wrong and needed to be educated by a recipient of the email; here’s how he corrected me:

“…the expression, that you used, as I understand it, is properly spelled, “well HEELED”. It now means rich or with money, but originally it was referring to weaponry, and making comparison to the roosters in cockfights.  Roosters fight by using the natural spurs on the backs of their feet-the heels-and the handlers of the roosters strap on sharp metal knives to make the birds fights truly bloody to-the-death fights. Each rooster handler has their own ideas about how the blades should be designed, and roosters with effective blades are said to be “well heeled”. The expression began to be used in reference to men who were carrying effective weapons, which are expensive, and thus the connotation shifted from a guy who has weapons, to a guy who has money…….also, some folks think it means a guy who is not down at the heels, who has fancy new shoes……but I think it’s mainly from the weapons thing….”

So, there you have an explanation for the origination of the phrase “well heeled”.

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