Portnoy’s Wild Crypto Gamble: XRP, Bitcoin, Ethereum and Tears of Regret

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Ah, Dave Portnoy-an entrepreneur who’s never met a gamble he didn’t like, especially when it comes to cryptocurrency. In a rather dramatic reveal, the man behind Barstool Sports, who has as much restraint as a dog in a meat market, recently disclosed his latest financial escapade: a cool $1 million worth of XRP. Yes, you read that right. One million bucks, gone in the blink of an eye. And as if that wasn’t enough, he casually tossed in $400,000 of Ethereum and $750,000 in Bitcoin, like they were party favors at some self-congratulatory soirée. 🤑

Now, according to the ever-reliable CoinGecko, XRP is currently worth $2.22-a mere 9% drop from the previous week. It seems even the mighty XRP is not immune to the turbulence of crypto’s emotional rollercoaster. But don’t worry, Portnoy is just warming up.

Not a Die-Hard Holder, Just a Casual Gambler

Flashback to December 2024, when Portnoy had the audacity to claim he held a staggering $1.3 million in XRP, alongside a hefty $1.5 million in Bitcoin. Of course, he described his “strategy” as “bet it and set it,” which is another way of saying, “I have no idea what I’m doing, but I’ll ride the wave.” But here’s the kicker: he admitted he was “always late to these runs”-as though time itself was conspiring against his financial genius.

Fast forward to early 2025, and Portnoy, ever the optimist, purchases another $1 million of XRP during a market dip. Why? Because why not? 💸

In mid-July 2025, as the crypto world buzzed with activity, Portnoy posted a video on X (formerly Twitter) revealing that he’d sold his XRP “two weeks ago.” No, this isn’t a typo-two weeks before the surge. Of course, this was no ordinary sale: he sold at $2.40 per XRP, all because someone-presumably a genius-told him Circle (the company behind USDC) might throw a wrench into Ripple/XRP’s grand plans. A move, no doubt, that he now regrets, as XRP surged 60% after his exit. And what did Portnoy do? He publicly lamented, saying he “wanted to cry.” A true crypto tragic hero.

First Crypto Exposure: A Winklevoss Encounter

But how did this all start? Well, let’s rewind to August 2020, when the Winklevoss twins (those crypto evangelists) came knocking on Portnoy’s door. They sat down with him, explaining Bitcoin as though he were a child learning to tie his shoes. The result? Portnoy bought his first Bitcoin, which-surprise!-he later declared to be worth a tidy $100K. And thus began his inconsistent love affair with cryptocurrency. But what can we expect from someone who claims to have a “strategy” yet still stumbles like a blindfolded bear on roller skates? 🙃

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2025-11-18 21:34