Illustration of a retro slot machine with dollar signs, stock charts, and dice on the reels, symbolizing insider buying and risk-taking at Penn Entertainment.

Penn Means No More Pain? Insiders Bet Big, and the Casino Isn’t the Only One Taking Bets...

Stock Ticker: PENN 🪙 
Price: $15.08
Change: +0.42 (+2.86%)
As of: May 23, 2025, 4:00:00 PM ET


🔥 Insiders at the Table... Again and Again

Executives at Penn Entertainment are doubling down harder than a blackjack addict with a caffeine buzz. Here’s what recent insider buying looks like:

🧑💼 Insider Activity Highlights:

  • Jay Snowden (CEO/Pres):
    ➕ 34,000 shares @ $14.70 = $499,766 (May 22)
    ➕ 54,200 shares @ $18.44 = $999,448 (Sept 3, 2024)

  • David Handler (Director):
    ➕ 10,000 shares @ $14.83 (May 22)
    ➕ 40,000 shares @ $14.94 (May 29, 2024)
    ➕ 40,000 shares @ $15.61 (May 6, 2024)

  • Others (incl. CFO + Directors) also showing bullish buys.

📈 Translation? Management seems to think the odds are finally shifting.


🏦 Institutional Chips Are In

Penn isn't just backed by its own brass. Institutions own 101.2% of the float. That’s right—more shares than actually exist, thanks to options and short lending.

🎓 Top Institutional Holders:

  • BlackRock: 17.49M shares

  • Vanguard: 16.25M

  • HG Vora, DME Capital, Invesco, State Street...
    🎰 When the pros are betting, you pay attention.

🔍 For full Institutional Ownership breakdown, see here.


🧠 The Business: More Than Just Slots & Shots

PENN isn’t your grandma’s smoky casino stock. It’s a 28-jurisdiction entertainment empire with major muscle in:

  • 🎲 Retail Casinos – Hollywood Casino®, L’Auberge®

  • 📱 Online Sports & iCasino – ESPN BET™, theScore™

  • 🧠 Tech Stack – Proprietary digital platform & in-house iCasino studio

  • 🎁 Loyalty Program – Over 32 million PENN Play™ members cashing in across digital and physical experiences

With ESPN and theScore in its corner, PENN is blending old-school and digital like a cocktail served in the metaverse.


💥 First Quarter 2025 Earnings Highlights

  • Revenue: $1.67B (up YoY)

  • Net Income: $111.5M (versus a loss in Q1 '24)

  • Adjusted EBITDA: $173.3M

  • Record iCasino Gaming Revenue despite sports betting losses

  • $35M in Share Buybacks (aiming for $350M in 2025)

  • Cash on Hand: $591.6M

  • Debt: $2.1B

  • Liquidity: $1.5B

  • Forward P/E: 35.84 😬 (Not dirt cheap, but not a slot-machine jackpot either)

🃏 Key Insight: Online casino is growing fast, with standalone apps in Pennsylvania, Michigan, New Jersey & Ontario gaining traction.

👉 Want the full picture? Dive into Penn Entertainment’s financials here.


🧮 By the Numbers

Metric Q1 2025 Q1 2024 % Change
Revenues $1.67B $1.61B ⬆️
Net Income $111.5M -$114.9M 💥 Big Turnaround
Adjusted EBITDA $173.3M $101.4M
EPS $0.68 -$0.76 🧮
Share Buybacks $35M YTD 🔁 Ongoing

⚠️ Risks to Watch Before You Bet It All

  1. 🥊 Heavyweight competition from DraftKings, FanDuel, etc.

  2. 💸 Consumer-sensitive business—a recession could fold the hand.

  3. 🏈 ESPN BET still a wildcard—huge potential, unproven payoff.

  4. 📉 Still down 90% from 2021 highs. Could be a bargain—or a mirage.


🧩 But Here’s Why It Could Work

  1. 🎰 Focus on Higher-Margin iCasino is driving record results

  2. 💼 Disciplined capital allocation with active buybacks

  3. 🤝 Institutional and insider buying = strong confidence signal

  4. 💵 Debt metrics improving after peaking pre-pandemic

  5. 🪙 Contrarian Setup – Losses contained, signs of a turnaround emerging

Interested in another investment idea?
Check our take on UnitedHealth Group.


🧂 Our Take

PENN’s stock has been painful—but insiders and institutions aren’t flinching. With digital growth, buybacks, and a bounce-back in profits, it might just be the turnaround you didn't see coming. But this is still Vegas, baby: bet responsibly. 🎲


📛 Disclaimer:

Not everything is a Penn in the Butt—but don’t bet the farm on a gut feeling. This isn’t investment advice, just some financially-flavored fun. Do your research before anteing up.


🧭 Want More Like This?

👉 Browse our Insider Purchases Center
👉 Explore Turnaround Plays 
👉 Or go international with our Global Investing Hub

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