What happens if you have tail, head, tail, head, head?
Round 1. Bet $50, tail, = $50
Round 2. Bet $25, head = $75
Round 3. Bet $37.5, tail = 37.5
Round 4. Bet 18.75, head = 56.25
Round 5. Bet 28.125, head = 84.375
You fall short of $200 even though you won the game.