To make a man bleed is to make him pay dearly for something; to victimise him. Money is the life-blood of commerce.
It makes my heart bleed. It makes me very sorrowful.
“She found them indeed,
But it made her heart bleed.”
Little Bo-Peep.
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Entry taken from Dictionary of Phrase and Fable, edited by the Rev. E. Cobham Brewer, LL.D. and revised in 1895.