$14,000 seems really low. Even if the hypo takes place in Memphis, where rents are low compared to, say, San Francisco, that’s just barely covering their expenses. That spare room must have been fairly nice, given that it had a separate entrancve and a power outlet sufficient for a refrigerator. I’d expect the rent alone to be $800 or so, and the increase in utilities ies to be a few hundred more. If nothing else, the now-filthy rich Jonathan should make sure the friends who kept him from being homeless and let him start rebuilding his life come out substantially ahead on the deal, now that he has the means.
I’d give at least four million. That’s enough to fund a comfortable retirement, but I’d probably have to talk to a CPA to figure out how to do it with the least onerous tax implications for all involved.
Not a penny. Screw the guy for being nice. No good deed should go unpunished.
I don’t think anyone has mentioned that if Johnathan wasn’t living rent free, would he have had the money to be playing the lottery? Is that not a luxury that was afforded him by Patrick and Beverly? Even if it wasn’t, paying back the equivalent of what he would’ve paid to stay there for a year is hardly generous, certainly not as generous as they were towards him.
Johnathan is a dick.
Buffay the Vampire Layer.
I can’t tell whether you’re serious, though I hope not. If you are, why do you feel this way?
I did. Don’t feel bad - no one else reads my posts either. 
I mentioned it because my friend bought new speakers rather than pay the rent he owed me. AND somehow managed to convince himself that he didn’t really owe me the money anyway.
He paid what I feel like would be the minimum in that case, but when you have riches beyond your dreams doing just the minimum to pay back someone who did you a favor seems unkind. I wouldn’t complain to him, and I’d be glad to have the cash, but I don’t think I’d feel that great about it. If I won the lottery in that situation, I’d do something more grandiose like pay off their house.
I would feel somewhat similarly to Patrick. But I wouldn’t say anything and wouldn’t interfere with their friendship. But 30k is pretty stingy…
Putting myself in either Jonathan or Patrick’s shoes, the $30k seems exceedingly small. As a grateful Jonathan, I would generously give up at least $300k of my after-tax $100m windfall, or ten times as much as in the tale. Presenting the check in terms of rent or expense reimbursement is offensive and silly, and doesn’t speak to friendship or gratitude, at all.
As a green-eyed Patrick, I would look at $30k as somewhat insulting and expect more. No, Jonathan doesn’t owe anything, as presumably reimbursement after getting a high-paying job or winning the lottery was never a condition of shelter. But, c’mon, $30k isn’t even pocket change for someone who just won $100 mil.
You can give $14k to each person before it bites into lifetime estate tax exclusions. So he could give the couple $28k. He could also directly pay hospital bills, school tuition or give to any (unmentioned?) children. Hell, you really want to play games, does one of them have semi-wealthy parents? Give them each $14k on the condition they turn around and gift it to the couple.
And hell, there’s nothing saying you couldn’t do that for several years running.
I yield to superior accounting knowledge, though I’m sure that, with $100 milion dollars, Jonathan could hire an accountant who could devise a way to give Beverly and Patrick bigger gifts. And if neither has wealthy relatives from whom they’d inherit, they may not care about inheritance taxes.
Oh, and kids were specifically mentioned in the OP; Patrick & Beverly have two, Jonathan has none.
I think after the demand, I would set up a $1 million trust fund for their kids. 
What demand? Patrick is specifically said not to have asked for anything more. It’s not even clear to me that he shared his misgivings with his wife .
↑ ↑ ↑ This with a condition. Well, two.
The kid and Bev’s money would be set up that even if they died, Pat could not get the money, it would go back into a trust or or something. I would actually do this to/for all three with no explanations given.
They would not even know what the others got unless they decided to tell them. They would not be able to give access to the money to each other, only physically take it out and hand to them.
I have seen such trusts so… I do not trust people to remain human when money, stress, stupidity, addictive behavior, etc., develops even if at the start their was no indication of it.
YSYMYW as will I.
I must be a softie. If these were really my good, good friends and they had plucked me off the streets in my dire situation I would expect to share ~10% of the windfall with them. What’s the point of having money if you can’t spread it around?
You’ve got a couple of tax things backwards. The estate/gift tax is paid by the person giving the money or by their estate after they. So Jonathan is the one who pays that tax and he’ll pay a lot of it unless he just totally squanders his fortune.
You can give $14,000 per person before reporting the gift and the tax code simplifies things a bit by letting you say that a single gift was split between a married couple. The same isn’t true for kids, so a gift to the kids must really be a gift to them, not just to their parents.
Phrasing the $30,000 as payment of rent might be a tactic by Jonathan’s tax advisor to give money away without having to call it a gift. As such, it would be necessary for the rent amount be reasonable.
Anyway, Jonathan needs to get used to Patrick’s attitude. It’s a flaw in human psychology and perfectly illustrates how most of us let emotions run our finances even when we think we’re being rational and logical about it. Lottery winners are either going to learn to cope with people like Patrick or they’re going to go bankrupt.
I started off think Patrick was a greedy asshole… but in thinking about it more fully a year of room and board is such an amazing gift to someone in his position to offer $ 30,000 is not all that generous if you are getting 100 million. It’s kind of chintzy relative to the benefit they gave you and your new fortune.
Patrick is being greedy and overreaching at 1 million but Jonathan (IMO) should be kicking in at least $ 100,000 or so out of gratitude. Both are being greedy but that’s what big money does to you.
$30,000 was a fair deal. More than fair is expected in these circumstances since Jon got a more than fair deal for a year. Patrick is acting like a jerk. So is Beverly, she should also consider that Patrick put himself out for her friend and something special was due back. Now Jon has no particular reason to give 1 million bucks to Beverly and Jon, that’s over the top. I think on top of the 30 grand to cover rent and expenses he should have sprung for nice cars for Pat and Bev, and offered to pay off their mortgage if they have one. Doesn’t have to be exactly that, but something that’s more of a gift and directed at their lives than just a pile of cash.
100 million? He lived with them for a year?
He should pay off their house. Minimum. Maybe send them on vacation too.