I don’t think we’ve ever talked about Penn Entertainment here at Stocks.News… and that might’ve been a crime. Because this stock has everything we love: corporate drama, eyebrow raising insider buying, meme stock potential, a proxy fight, and Dave Portnoy pulling off the greatest “I told you so” in modern business history (at least, in my opinion).

So let’s catch up on the endless content machine that is PENN, because between a near-$500K insider buy and some very bullish options activity, this might be the most under-the-radar “screaming buy” we’ve seen all year. Once upon a time (read: January 2020), Penn dropped $163 million to buy 36% of Barstool Sports, hoping that Portnoy’s army of “degenerates” would become loyal ESPN Bet users. Fast forward to 2023, and they’d sunk another $388 million to grab the rest… for a grand total of $551 million.

And then… they sold it back to Portnoy for $1. That’s not a typo. One dollar. Four quarters. Roughly the cost of a gum ball. A whole media brand tossed back like a piece of trash. The reason? Barstool’s brand proved too difficult to manage within the strict regulatory environment of online gambling. Its edgy content, combined with Portnoy’s controversial public persona, drew scrutiny from state regulators. That friction created a compliance migraine Penn couldn’t afford as it pushed to expand digital betting operations under intense government oversight. So rather than fight an uphill battle trying to make the Barstool partnership work, they cut ties and handed it back… at a massive financial loss.

But here’s where it gets even more compelling: Portnoy now owns 100% of Barstool again and Penn has a 50% cut of any future sale. So if Portnoy flips it in five years for, say, $400M? Penn might accidentally win that breakup. Legendary. Right after offloading Barstool, Penn inked a 10-year, $2 billion deal with ESPN to rebrand its sports betting platform as ESPN Bet. On paper, it looked brilliant. ESPN has brand recognition, access to every sports fan on Earth, and probably your dad's trust.

In reality, ESPN Bet has been kind of… mid. Despite the hype, they’ve only grabbed 2.35% market share in online sports betting… nowhere near the projected 20% by 2027. They also lost $109.8 million in Q4 alone. To be fair, a lot of that came from botching the rollout… like forgetting to add sign-up bonuses in New York, which is like opening an ice cream shop and not serving cones. But now the pressure is on… and that’s when turnarounds get fun.

Penn’s biggest shareholder, HG Vora Capital, owns 18.5% of the company and said “nah, we’re not doing this anymore.” They launched a proxy battle, trying to take over the board and shake things up. They think Penn’s management fumbled the bag with its digital strategy, overpaid for ESPN Bet, and needs to refocus on what it actually does well… you know, like running 43 casinos across 20 states.And it looks like they might be winning.

Penn just agreed to add two HG Vora nominees to the board, and the shareholder drama is far from over. Some analysts think the endgame could involve selling off ESPN Bet, or even shopping the entire company. And if that happens? The upside for current shareholders could be massive.

And just when it felt like things couldn’t get any more dramatic… Penn CEO Jay Snowden showed up with his checkbook. On May 22, Snowden bought 34,000 shares of Penn stock at around $14.70, dropping $499,766 of his own money. And no, that’s not one of those “pretend buys” CEOs do to impress the board. Dude already owned over a million shares… this is a top-up, not an entry point. Let me put it in degenerate gambler terms (in case that’s the only language you speak): if the CEO doubles down on a stock down 22% YTD… he either knows something we don’t, or he’s trying to save face before HG Vora (Penn’s largest shareholder) fires him.

And other folks with deep pockets kinda like the stock. We’re seeing bullish options activity explode, with 12,485 calls traded (5x the normal volume) and a Put/Call ratio of 0.01… aka no one’s buying puts). Most of that volume is targeting near-term strikes like the $16 weeklys and $17.5 June calls. That smells like smart money betting on a near-term breakout. Penn’s market cap is just $2.07 billion right now. That’s not much when you consider they: run dozens of profitable physical casinos, have a 10-year ESPN branding deal, and just restructured their board.

Analyst price targets average $21.30, with some calling for $30… meaning you're looking at 40% upside to the average, and nearly 100% to the high. Not bad for a company with real assets, a turnaround in motion, and a pissed-off hedge fund breathing down management’s neck.

Now toss in a massive insider buy and options traders piling in like Nancy Pelosi… and you've got the ingredients for a monster rebound. I’m not saying to bet the house on it. But a small side wager might be worth the chips.

Stock.News has positions in Disney.