Of course if he got GC he won't have any problem. You have the golden paper and you are all set. But main question remains the same. How would he will obtain the GC without leaving the country ?As far as I know GC is an adjustment of status (if it is filled through employment) and to get a new status he has to leave the country.

Regarding adjusting status with lots of money and luck, I am not sure what does that mean ? Will you be able to provide any details?