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The high school math teacher at Riverdale Country School in the Bronx answered eight questions correctly and used two “Jump the Question” lifelines to make it to the second round of questions. There are four questions in round two, which are increasingly difficult and worth more money.
The first question of round two was: The Isle of Man is a self-governing dependency located off the coast of what country? Unsure of the answer and without lifelines, Greenstein decided to walk away with the money he had earned in round one. If he had guessed incorrectly, his winnings would have been cut back to $25,000. The answer was England.
The Livingston native said in a release that he would like to buy a home in Westchester and that his winnings would go toward that purchase. He also would like to plan an extra-special trip to Disney World, where he and his wife, Dana, go every year. He proposed to his wife during a visit to Disney World, according to the release.
For inspiration, Greenstein said he watched a YouTube clip of first "Millionaire" winner John Carpenter's performance on the show.
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