According to "Fortune's Formula: The Untold Story of the Scientific Betting System That Beat the Casinos And Wall Street", the probability of losing half initial money at some point using Kelly's criterion is 50%. This is written without any proof. How to prove this?
If situation is too complex, I want to know the special case, where the winning probability is 50% and return is 200%, the losing probability is 50% and return is 50%. The expected return is 125% > 0. So this gamble offer good odds. According to Kelly's criterion, the optimal strategy is to bet half of total money.
In this case, what's the probability of losing half initial money at some point?
As herb steinberg commented the expected return for a bet of $1$ is clearly $\frac{2+0.5}{2}=1.25$, i.e. an expected profit of $0.25$.
It seems in this case, the probability of losing half or more of your original bankroll is nearer $0.44$ than $0.5$ as suggested by these $100000$ simulations of $1000$ successive Kelly criterion bets
It is possible to do very badly early on with the Kelly criterion, even if it is later recovered. In the simulation the worst worst case lost $99.999934\%$ of the initial bankroll, before recovering to many thousands times the initial bankroll. The overall distribution of worst cases is illustrated in this graph.