Howie Rubin, "lost more money on a single trade than anyone on the history of Wall Street."
The relevant headline and article in the Wall Street Journal on April 29, 1987 read:
"MERRILL HAS $250 MILLION LOSS ON UNAUTHORIZED TRADING
Executives at Merrill Lynch privately identified the trader as Howard A. Rubin, 36 years old, who had been the firm's head mortgage trader. They said he had far exceeded his limits in acquiring mortgages that were packaged into a particularly risky form of securities. The package involves splitting off the interest payments on the mortgages from the principal and selling each separately. They are known as 'interest-only/principal-only' securities, or lOPOs."
https://archive.fo/pdxtv