Proebsting's Paradox refers to a situation in which a sports trader makes successively increasing bets on the same selection in a single market, ostensibly using the Kelly Criterion to calculate the stakes while taking advantage of better and better odds, only to ultimately face ruin.
The difficulty arises because the sequence of bets appears to cost more in total bankroll percentage than the Kelly Criterion would recommend as a standalone bet at the highest odds in the sequence.
In the Todd Proebsting example, the sports trader initially bets 25% of his bankroll on a 2/1 selection with a 50% win probability. Some time later, he is offered 5/1 on the same selection and calculates his Kelly stake at 22.5% leading to a total wager of (250 + 225) = 475.
The problem with this result is that the Kelly stake for a single bet at 5/1 (assuming 50% win probability) is only 40% of bankroll (400) - leading to the theoretical possibility of ruin from betting at successively more attractive odds on the same selection in a single market.
To resolve this paradox, both Ed Thorp and Aaron Brown recommend that the sports trader should "mark to market" his bankroll after the initial 2/1 bet (reducing it by 12.5% from 1000 to 875) and use this updated position to calculate the 5/1 stake. In fact, to stay within the upper limit (400) defined by the standalone 5/1 bet, the trader also needs to reduce his estimated win probability to 42.5%!
Using the above example, this would lead a sports trader to bet at most 146.25 = (16.71% * 875) at 5/1 giving a total wager of (250 + 146.25) = 396.25, which is roughly equivalent to the Kelly standalone stake (400) at 5/1 but with a lower upside!
