The money won't be coming from his pocket I'm sure
I don't think much has over the years despite what people believe.
When we were bleeding money he did. But according to the club we're not any more, so I would take from that his monetary input isnt needed as much any more
The majority of the money he put in was loan or in exchange for equity, the money loaned is being repaid and has in the past been subject to management fees and interest (low level and not always waved) I believe.
As and when he sells the club I don't expect in real terms he will have put much if any of his money in.
Not that that is wrong in any way, but I think there is a misconception with him that he has been some kind of generous benefactor to the club and I don't think that view stacks up personally.
For him not to lose money he needs to sell for 250m or more. He will lose money.