Would Ross have to pay any of that considering he will be in prison for rest of his life ?
Yes. He has to pay it. If he doesn't, they take all money away from his parents and sister and leave them on the street. It is very harsh to be under the government of the US
That is not how it works. They don't make the relatives pay his debt. What they do is they took all the sales from his bitcoin and applied it to his debt. What ever amount is over that, he then has to pay through work. While in prison he may make $1.13 an hour or some crappy number. The government takes half or so to pay his debt. If he gets any money sent to him they take money to apply to his debt. It is a messed up system and ridiculous. If he does not work they may take his privileges, lock down, or solitary confinement. I believe in federal prison all able bodied prisoners are required to work. They said they abolished slavery but it is going on in our prisons.
Edit:
Just saw an article last year that the maximum wage in federal prison is $1.15 an hour.