To be honest, I do not know if you concept would catch on. When you gamble on other sites, you know what the house edge is and it is usually between 5% to 10%. < These gamblers have a good chance to win back between 90% to 95% of the money they gamble and sites with a higher house edge, sometimes gives a rake back option for people to get back even more >

Let's say Bob keep on losing, because his share of the "Jackpot" is always in Alex's favor, then he will eventually stop gambling. The guys with the big pockets will crush the gamblers with the smaller pockets. In the off chance that Bob does win, he would have lost a lot more than Alex and he will not have more money to gamble anymore.

The trick with gambling sites is to create a scenario where the gambler think that he is winning the house and that incentivize him or her to come back and to gamble more. What motivation is there for Bob with the smaller pockets to come back?

Have you tested this with friends and family and what was their feedback?