Rose is being paid 300x more than the average Chicagoan because he has a skillset possessed by less than 0.000007% of the world's population. He's not making 300x more than the average Chicagoan with average Chicagoan abilities. He's not getting paid millions in salary and endorsements to play our level of Y-quality ball.
Yeah, it's interesting that I don't often hear the argument about excessive compensation for frivolous skillsets when people talk about actors or musicians, even though to a large extent it's the same thing.