Dave Grossman was a designer on The Secret of Monkey Island.
He was partially responsible for the rubber tree fake death gag on the Monkey Island clifftop. Having seen a crack in the cliff, he assumed that it was part of a puzzle and so drew a version of the cliff with the segment broken off. On learning that it was not planned to be included, the team instead took the opportunity to poke at the Sierra adventure games and their tendency to kill players too arbitrarily.