Friends with money

With that ugly truth stipulated and out of the way, let me add another confession. I have a friend who has made a fortune in the past few decades in the financial markets. He has been a phenomenally successful investor in many sectors and as a result has spent the past few years buying glamorous houses overlooking various bodies of water, flying in a private jet, drinking the very best wine, and treating his friends, me included, to a series of outrageously luxurious outings.

That’s not the confession part, by the way. The confession part is here: The past two years have been brutal to his portfolio, and his net worth has plummeted as a result. He’s a lot less rich than he ever was, and I am taking an appalling amount of joy at this financial downfall.

Let me be clear: He is my friend and I love him. He’s a generous and loyal guy, thoughtful and decent to everyone. A good and fair boss by all accounts. A dynamite host. But for some reason — well, I know the reason: I’m a terrible person — when it was clear that this bear market was hitting him hard, a part of me was quietly celebrating.

I know, I know. Shameful, right? He and I have been friends for nearly three decades, so I’ve had plenty of time to make my private peace with whatever envy and secret rage I had bubbling beneath the surface when, say, it was clear that he and I were living very different lives. This moment happened many years ago when I drove up to the cottage he had rented in Sag Harbor only to discover that it was the guest house to the house he bought on a grassy hill that sloped luxuriously down to the water where a Hinckley yacht was tied expensively to his dock.

You’d think I’d have made the appropriate emotional adjustments by now, but apparently I have not. (See “not a nice person, reasons” above.)

We met last weekend for a long walk and a cigar. I listened as he told me that he’s thinking of cutting back on travel and entertainment expenses. He was thinking of selling the Miami Beach condo and the place in Connecticut. He was furious with himself for putting so much of his personal wealth at risk.

Look, he’s still a very rich guy. But I’ve discovered that rich people have very strict and inflexible definitions of personal wealth. He’s a very rich guy, but he’s no longer an extremely rich guy. That’s a distinction that’s lost on a person like me, who has basically zero trouble doing my taxes each year. But it’s killing him.

Which of course makes me perversely happy because for years I’ve told myself, Hey, more money, more problems, right? Even though I do not believe that for a moment. More money, it’s always seemed to me, means fewer problems. Maybe even no problems at all if you spend it right. But here I was walking with my friend and listening to his genuine distress and feeling really good about myself.

“You know what the worst part is?” he asked.

“Flying commercial?” I said.

“It’s not as bad as that,” he said. The worst part, he told me, was the nagging feeling that a lot of his so-called friends would drift away from him now that the weeklong parties and the Chateau Petrus and the place in Careyes were gone.

I put my arm around him and gave him a squeeze. I told him that he has real friends, lots of them, who never cared whether he had money or not. Hell, I said, some of them may even like you more now that you’re not so stinking rich. And then I laughed as if to say, Wouldn’t that be weird and creepy? He laughed.

“You’re a good friend,” he said to me.

What could I do but agree with him?

Rob Long is a television writer and producer and the co-founder of Ricochet.com.