The list of possible outcomes changes, but the expected outcome does not.<p>2x winnnings * 50% chance of winning * 20 games * $1 per game = expected outcome $20<p>2x winnings * 50% chance of winning * 1 game * $20 per game = expected outcome $20<p>Your fuzzy logic around &quot;winning big&quot; &quot;losing big&quot; etc doesn&#x27;t change the basic math of the expected outcomes, which is simply (chance of a thing happening) * (result if it happens).