Portnoy moves to cash out majority of Penn stock and could profit $30M

Hands pushing poker chips
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During his emergency press conference announcing his repurchase of Barstool Sports, founder Dave Portnoy referenced his Penn stock and suggested he was going to sit on them.

“I still own a ton of Penn stock. I’ll probably hold it because I think it’s gonna go up,” Portnoy said at the time.

As Sportico first reported on Friday, Penn Entertainment filed notice with the SEC that Portnoy intends to sell 1.25 million of the 1.48 million he owns (his stock represents roughly 1% ownership of the company). While the document is not a guarantee

The shares were issued to Portnoy in February of this year as part of the finalization of the sale of Barstool Sports to Penn.

Per the filing, Portnoy has until Aug. 17 to sell shares under the current agreement:

“On or after August 18, 2023, the selling shareholder may only sell securities under Rule 144 or any other exemption from registration under the Securities Act, if available, rather than under this prospectus supplement. The selling shareholder is not obligated to, and there is no assurance that the selling shareholder will, sell all or any of the common stock we are registering.”

If he is able to share around the $24 price $PENN was trading at on Friday, Portnoy stands to make an additional $30 million. He also retained control and ownership of Barstool Sports from Penn for $1 and some non-compete clauses. However, if Portnoy is to sell Barstool again, Penn would receive 50% of the proceeds.

Penn stock prices shot up as high as $31.38 per share after the announcement it would be launching ESPN BET. The prices have quickly come back down and are on pace to close Friday at less than what it was trading on Monday, which was $24.84 per share.

On his emergency press conference, Portnoy said he would never sell the company again. Of course, he also said he would hold on to his Penn stock.