I am suggesting that even £19m doesnt put him in the wealthy privileged class he still asks all his old managers to enter the ballot and if succesful he pays for the ticket and gives us a financial reward.
But you've given us an example where those rich enough, can simply buy a ticket (within a package deal). Your fabulously wealthy ex-boss could just buy one if he wanted.
Or he could try to get one via a snide, completely against the rules fashion - turning his ex-employees into touts.