Jane Street–styleTraderAssistant TraderQuestion #216

You play a game where you roll a 100-sided die labeled with the numbers 1 to 100. After each roll, you may either accept the payout equal to the number rolled in dollars or pay $1 to roll again. You can continue to pay $1 to reroll as many times as you like until you choose to accept your current roll. What is the optimal strategy for this game, and what are your expected winnings using this strategy?

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