How Barstool Prez & New Penn Partner Became Davey Day Trader And Lost $1 Million

Written By Kevin Shelly on April 23, 2020 - Last Updated on August 5, 2022
Davey Day Trader learning hard lessons

Barstool Sports founder Dave Portnoy‘s learning curve about the stock market in his new personae as Davey Day Trader Global went on full online display a month ago.

That was about the time his new stock holdings in Penn National Gaming came crashing down.

Muzzled about Penn stock, Portnoy remade himself

Since March 23, he’s live-streamed during trading days via his blogsite and Twitter feed, which has 1.2 million followers.

But as a stakeholder in Penn, a relatively staid Pennsylvania-based gaming company which was looking to make a splash entering online sports betting under the Barstool brand name, he’s muzzled by trading rules.

That seems like a part of the impetus for his entry into day trading and live streaming about his other new investments. Portnoy has so far managed to not talk about Penn during his unscripted live video feeds.

‘Don’t trust anything I say about stocks’

Portnoy, who goes by @stoolpresidente on his millennial-oriented sports and lifestyle online platforms, spells it out right below his Twitter handle:

El Presidente/3 time Bee Sting survivor. I own a ton of Penn Stock. I’m not a financial advisor. Don’t trust anything I say about stocks. Owner of DDTG Global

Barstool received $135 million in cash and $28 million in stock in the deal with Penn National. The agreement calls for Penn to invest another $62 million in Barstool within three years while boosting its stake in the company to about 50%.

Portnoy has a partner, The Chernin Group, which previously owned the majority of Barstool, but now holds a 36% share.

What goes up will come down

The value of his Penn stock (PENN) started at $26.21 per share in February, when the deal was announced. It hit above $39 a few weeks later.

But virus restrictions took hold and upended markets.

Penn furloughed 26,000 employees, and also sold assets and tapped credit to ride out the storm. They also halted construction on two mini-casinos being built.

Penn shares hit a low of $3.75 on March 18. It’s been volatile since but is back up over $13 a share this week.

Portnoy’s streaming of his life as a stock trader began five days after Penn hit bottom.

Portnoy wanted a platform

Adam Mesha veteran day trader, is relatively sure why Portnoy decided to become a trader streaming in real-time.

Mesh has a unique perspective.

Not only is he a successful stock trader with more than two decades of experience, but his Manhattan office is also two buildings down from Barstool’s headquarters. He’d even proposed teaming with Barstool for stock trading coaching, but nothing came of it.

Mesh recently wrote about Portnoy and Penn’s volatile share prices for

All of this movement was out of Dave’s control and that’s not a good thing. Portnoy likes to be in control and he also has a tremendous appetite for risk… Being unable to stop the PENN bleeding was painful but what was much worse was his inability to talk about it. You see, prior to the PENN dream, the only SEC Dave knew had Alabama and LSU in it. Now he had to learn about the other SEC, the Securities & Exchange commission.

We’ll come back to Mesh’s observations, but first, more on Portnoy himself, who was already known for his bad bro behavior. That has included, among other things, slut-shaming a former girlfriend online and berating the looks of a female employee while live on air.

Bezos is ‘that bald —-‘ in Portnoy’s complaints

His live stream, alternately boring while he quietly watches a computer screen, and entertaining as he screams epithets – Amazon owner Jeff Bezos is a favorite target – and launches rants in his Massachusetts accent as yet another stock pick disappoints.

The following is a sampling of his ranting. (Warning: explicit language contained within.)


Tearing off the glare-filtering glasses from Felix Gray he touts – they have underwritten some of his feeds – and then twisting them in half, Portnoy told his many fans on April 21 he’d lost about $1 million since his trading began.

One stock site put his initial trading account at $3 million.

Tuesday did not go well for Portnoy

As Portnoy said live Tuesday as he squeezed a wad of currency like a crushed worry ball:

“This could be the end of Davey Day Trader.

“I go home to change my shoes, I come back, lost $200 grand.

“Oh —-ing so much money.

“I don’t even care. Down a million dollars, today. Amazon’s down 5%.”

Portnoy has made bad deals on not just Amazon, but also on Boeing, which he reverse-shorted, a coffee company, and the yoga wear company, Lululemon.

Oops, Portnoy pressed the wrong button

While Portnoy said he made $250,000 on Wednesday, he also committed a major screw up at the end of the trading day when he tried to sell 580 shares of Amazon.

He hit the wrong button and instead bought an additional 580 shares, which led to a new Bezos rant.

His stream drew more than 100,000 viewers Wednesday for the more than six hours Davey Day Trader was online.

‘You don’t know what you don’t know.’

Mesh, the professional day trader, has watched with interest, as you might while passing a long car pileup.

“It’s so entertaining!” he said, quickly adding, “I would not associate anything positive with it.”

He does, however, find Portnoy’s pizza reviews “mindlessly addictive.” They were a regular feature of Barstool’s before the Davey Day Trader channel began.

Mesh said he’d seen Portnoy “completely thrown for a loop” by some market actions, adding the Barstool personality is learning “all the lessons” the hard way at warp speed.

“You don’t know what you don’t know,” he added.

‘A one-man show’ and the ‘Barstool effect’

Mesh said Portnoy appears to rely on his fundamental beliefs without examining the technical aspects of a stock.

“Sometimes there’s no rhyme or reason,” which leads to Portnoy’s investments “for all the wrong reasons.”

Some days Portnoy appears “to be falling apart a little,” said Mesh. “He’s a one-man show.”

Mesh believes Portnoy’s ownership of Penn National stock brought his youthful followers to Penn as buyers of the stock.

At first, the rookie investors drove the stock price up, Mesh believes, but when the markets sank, it added to the volatility of the shares as the Barstool faithful bailed.

“We call it the Barstool effect.”

‘I don’t think this ends well.’

While Penn stock has rebounded modestly, Mesh does not see Penn or its deal with Barstool as a good long-term investment.

He pointed to a glowing forward-looking statement this week from Penn’s CEO predicting strong future growth in digital wagering – which is still under development – due to the Barstool deal.

Mesh pointed out a former Forbes editor and hedge fund manager, Will Meade (@realwillmeade), who then posted the Penn letter on his Twitter feed with a one-word introduction: “Laughing.”

“This does not look like a stock you give to your worst enemy,” said Mesh. “I’d rather be on a cruise ship than owning Penn National Gaming.”

And as to Portnoy’s foray into stock trading?

“I don’t think this ends well.”

Kevin Shelly Avatar
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Kevin Shelly

Kevin C. Shelly is an award-winning career journalist who has spent most of his career in South Jersey. He's the former assistant city editor of The Press of Atlantic City, where he covered the casino industry and Atlantic City government as a reporter. He was also an investigative, narrative enterprise, and features reporter for Gannett’s Courier-Post.

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