Before cockfighting was banned in 1849, individual birds were often fitted with sharp steel spurs, giving them an advantage in mortal combat.
They were “well heeled.”
In the nineteenth century, the expression became slang for anyone armed with a weapon.
Then, around 1880, the term began to mean anyone who was well-off financially and who could overcome any obstacle with money instead of a weapon.
We still say that someone with money is “well heeled”.