The doubling staircase
Bet $1 on a fair coin. If you lose, bet $2. Lose again and bet $4, and keep doubling until the first win. If that win comes on bet , it pays after you have lost
so every run of the system ends exactly $1 ahead, which looks like free money.
Now give yourself a real bankroll of $1,023. That pays for ten bets, , and no eleventh. You walk away $1 up unless the coin goes against you ten times in a row, which has probability , and then you lose all $1,023:
The system wins 99.9% of the time and its expected profit is exactly zero. It swaps a long run of small wins for one rare cliff that wipes them all out. Run it every night and the cliff stops being rare: over 1,000 nights the chance of falling off at least once is .