bleed (v.)

Old English bledan, "to cause to lose blood, to let blood" (in Middle English and after, especially "to let blood from surgically"), also (intrans.) "to emit blood," from Proto-Germanic *blodjan "emit blood" (source also of Old Norse blæða, Dutch bloeden, German bluten), from PIE *bhlo-to- "swell, gush, spurt," or "that which bursts out," from suffixed form of root *bhel- (3) "to thrive, bloom."

Meaning "extort money from" is from 1670s. Of dyes or paints, "to be washed out," from 1862. Figuratively, of the heart, "to suffer anguish, feel pity or sorrow," late 14c.