On May 25, 1979, American Airlines Flight 191, on takeoff from Chicago O'Hare airport to Los Angeles International Airport, lost one of its engines (as in, the engine literally fell off the left wing of the DC-10 (1)) and crashed just short of a trailer park near O'Hare. All 271 passengers and crew were killed, along with 2 people on the ground. To this day, it's still the worst passenger plane crash in American history.
Among the passengers were Playboy managing editor Sheldon Wax, his wife Judith (who contributed to the magazine; most notably for her "Christmas cards" that were satirical poems to various public figures) and Playboy magazine fiction editor Vicki Halder, along with several members of the American Booksellers Association on their way to a convention, where they were to have a joint party hosted by...Hugh Hefner.
So, here's the WI: Hugh Hefner is somehow aboard AA Flight 191 and is killed.
Effects, anyone?
(1) It was later determined to be improper maintenance of the engine. This and the Turkish Airlines DC-10 crash (caused by an door malfunction which had been warned about after a similar incident in the US two years earlier), which killed 346 people, helped ruin the reputation of the DC-10 as a whole...