The guy has no shame. If we cut him out of our cabin this year, there is a good chance he will still show up down in North Carolina and crash on the couch.

But, there is no question doing so will end the friendship.

Everyone pays me at the end ... except the one guy. Three years in a row, he has not paid.

I feel the need to share some Kevin stories.

Why stop being a friend? He simply can't easily pay for this event. It's expensive, so what's the big deal. You enabled the mooching for several years, just stop. It doesn't have to be personal on your end. His reaction is his own to make. I have covered costs for friends who are less well off. Many years ago, friends would cover small costs for me. OTOH, I've never covered sizable costs for multiple years. Just be straight with him.

I'm going to guess that you and Brick ("gift it to him") are employed but not self-employed. If self-employed or own a business, you quickly learn to see through ppl's BS.
(Or as a friend once said, "What do you call a Democrat who owns a business?" A Republican.)
In our business, I often apply a courtesy or cut ppl a break. But when they impose a "discount" on us, by not paying? Oh hell's no.

I'm willing to bet that your so-called friend secretly, deep down, feels like this: Since you have so much more than him, you shouldn't care that he doesn't pay. You can afford it (and so much more), and you know that it's a stretch for him. An entitled attitude of wealth distribution.

I had a similar situation. He's no friend and either is your guy...

Hope it works-out for you one way or another.

Is he married?

Is he not paying because the wife controls all of the money and doesn’t “let” him spend money?
Or- does she know he’s doing this? If my wife heard i owed someone money, she’d make sure it got paid immediately.

Or- let’s say this guy is hard up for cash. This trip is the one thing he looks forward to all year.
Are the other guys friends of his?
If we had a buddy that was tight with the group, but couldn’t swing the cost, we’d all chip in to cover. (And maybe not equally. Big shot buddy might pay more). This has happened for several Vegas trips. And for weddings when a friend was invited but couldn’t afford the flight.

Ok old man. We've heard those before.

Is your son always complaining about you retelling stuff -- my kids do.

I'm going to guess that you and Brick ("gift it to him") are employed but not self-employed.

That's how I thought of it the first year. If there was even a semblance of appreciation, I could, perhaps, continue to go that route. Therein lies the rub, there is none. I appreciate your comment. It is what I am struggling with.

Everybody has that one friend who never seems to be able to find his wallet. But, has it ever gotten to the point it has ended the friendship?

I have a buddy who is the consummate mooch. I can put up with it most of the time. But, a group of us go to a car rally every April down on the NC/TN border. We rent cabins at a resort. Cost ranges from $350-450 per person, depending on how long we stay. This April will be my 4th time going.

I usually make the reservations, so the bill is on my card. There are 4 of us staying in a cabin. Everyone pays me at the end ... except the one guy. Three years in a row, he has not paid. That frosts me enough, but, the other guys are now upset that he is getting a free ride (and clearly taking advantage of me). So, this year, I set deadlines for payment payment of the 2017 amount and am requiring everyone to pay in advance for 2018. Everyone else paid for 2017 ... except this one guy. Everyone else is on track to pay in advance for 2018. Except this one guy.

He knows my address. He has my PayPal. I even sent invoices to everyone so he can pay online and doesn't even need a PayPal account. He says he has the money, but "wants to pay me face to face." That means he is going to give some sob story. My guess is he will have a post-dated check for 2017 lodging and will ask to pay after-the-fact for 2018. Mind you, it has been 11 months since we went in 2017 and he is the only one who has not paid.

In the past, I have never, ever allowed money to ruin a friendship, but, this is getting to be a bit much.

Anyone ever face a situation like this? What did you do?