Success in life is an incredibly complex game, maybe the most complex game. There are strategies one can follow and build upon to up their chances of success in life, and hypothetically if one were omniscient so that they could understand all of the random variables then they could judge whether somebody else "deserved their lot in life". If the player made all the best strategic moves given his input, and he also reaped those rewards, then he truly deserved his lot in life. If he didn't reap the rewards, then it's obvious he didn't deserve his lot. This is apposed to a purely stochastic game in which the omniscient individual would only be able to determine that the game's outcome had nothing at all to do with the player's moves.
In a hostile game in which other players are neck to neck with you(like the government and the capitalist elite in our corrupt game), you still have free will, it's just that exercising it in the most precisely strategic ways has become very, very valuable.