Start in 1972, on a horse track near Grantville, Pennsylvania. A family named Carlino is running Penn National Race Course - grandstands, betting windows, the smell of hay and diesel. Fast forward five decades and that single racetrack has become PENN Entertainment, a company operating 43 casinos and racetracks across 20 states, running online sports betting and casino apps, and holding a loyalty file of roughly 34 million people. The horses are still there. So is almost everything else you can bet on.
PENN Entertainment, Inc. (NASDAQ: PENN) is headquartered in Wyomissing, Pennsylvania, employs around 24,000 people, and books annual revenue near $6.96 billion. It went public in 1994 as Penn National Gaming and spent the next thirty years buying racetracks and regional casinos. Then, in the 2020s, it tried to become something else - a media and technology company that happens to own a lot of slot machines. That reinvention is the interesting part, and it hasn't been a straight line.
01What the company actually does
Two businesses live under one roof. The first is retail: casinos, racetracks, hotels and restaurants under brands most Americans recognize - Hollywood Casino and L'Auberge chief among them. This is the steady part. People drive to a property, play slots and table games, eat dinner, sometimes stay the night. It is a local, cash-generating business that has been PENN's backbone for decades.
The second is interactive: online sports betting and iCasino. Here PENN offers theScore Bet sportsbook and Hollywood Casino online, the latter ranked among the top online casino products in the United States and stocked with original games from PENN's own studio. The two halves are stitched together by PENN Play, a loyalty program designed so the same person can earn and redeem rewards whether they are on a casino floor in Ohio or placing a parlay on their phone.
"It is the right time to realign our interactive focus... to further leverage our core retail casino business and overall omnichannel business model."
Jay Snowden, CEO, PENN Entertainment02Who its customers are
Two crowds, one file. On the retail side, PENN serves casino, hotel and racing guests across its 20-state footprint - regional players who treat a Hollywood Casino as a night out rather than a destination flight. On the digital side, it serves online bettors and iGaming players in states where those products are legal, plus Canada. The connective number is the loyalty program: roughly 34 million PENN Play members. Layer on theScore media app, which carries about 4 million monthly active users in North America, and PENN has an audience most sports-betting startups would spend billions trying to buy.
03The problem it solves
Online sportsbooks have a famously expensive problem: acquiring customers. Bonuses, ad spend and promotions can cost hundreds of dollars per signup, and many of those customers never come back. PENN's pitch is that it doesn't have to pay full price. It already has millions of people walking through its doors and tens of millions in its loyalty database. If it can move those relationships onto the phone - and pull online players back to the property for a weekend - the customer-acquisition math looks very different than it does for a pure-play app.
slots · tables
34M members
app · iCasino
04How it got here
The corporate history reads like a company that kept changing its mind about what it wanted to be - because it did. The retail base was built patiently over decades. The digital reinvention came fast, and expensively.
- 1972The racetrackThe Carlino family begins operating Penn National Race Course near Grantville, Pennsylvania.
- 1994IPOPenn National Gaming goes public on NASDAQ on May 21.
- 2020New CEO, Barstool stakeJay Snowden takes over as CEO; PENN buys 36% of Barstool Sports for ~$163M.
- 2021theScorePENN acquires the sports-media company theScore for roughly $2 billion.
- 2022New namePenn National Gaming rebrands as PENN Entertainment.
- 2023Barstool out, ESPN inPENN sells Barstool back to Dave Portnoy for $1 and launches ESPN BET.
- 2025ESPN out, theScore backPENN winds down ESPN BET and rebrands its U.S. sportsbook as theScore Bet.
"When we first announced our partnership with ESPN, both sides made it clear that we expected to compete for a podium position in the space."
Jay Snowden, CEO, PENN EntertainmentThe line worth sitting with: PENN sold Barstool Sports back to founder Dave Portnoy for one dollar in 2023, after buying it in stages for hundreds of millions. That is not a rounding error - it is a company deciding a rented brand wasn't working and cutting it loose. It then rented another one, ESPN, and cut that loose too when market-share targets went unmet. The pattern is expensive, but it points somewhere: PENN keeps returning to theScore, the one sports brand it actually owns.
05Products and services
Beyond the flagship casino brands, PENN builds its own games through PENN Game Studios, which supplies original slots and table titles to Hollywood Casino online. Owning theScore also gave PENN a technology and media stack rather than a licensing agreement - the difference that seems to matter most after two failed brand partnerships.
06The business model
Most of the money still comes from the floor. Retail gaming - slots and table games at 43 properties - is the revenue engine, supplemented by hotels, food and beverage, and racing. The interactive segment adds online sports betting and iCasino, the fastest-growing piece: PENN reported iCasino revenue up roughly 40% year over year in a recent quarter. The strategic wager is that the retail base makes the digital business cheaper to run than it is for competitors who have to buy every customer from scratch.
07How it's different, and where it fits
In online betting, PENN competes with DraftKings, FanDuel, BetMGM and Caesars. In regional casinos, its neighbors are Boyd Gaming, Bally's and again Caesars. Very few operators sit meaningfully in both worlds. DraftKings and FanDuel are digital-first with thin physical footprints; classic casino operators are strong on the floor but weaker online. PENN's bet is that the middle - deep retail plus a credible app, joined by one loyalty program - is a defensible place to stand. The unresolved question, and the reason its stock has been volatile, is whether the two halves reinforce each other as neatly in practice as they do on the napkin.
Three sportsbook names in four years - Barstool, ESPN BET, theScore Bet. The lesson PENN paid for: in sports betting, brands you rent can be taken back. Brands you own, you keep.
Editorial analysis08The expertise
What PENN knows better than most is the unglamorous craft of running regional gaming and hospitality at scale - licensing across dozens of jurisdictions, operating hotels and restaurants, and managing a loyalty program with tens of millions of members. The newer expertise, bought through theScore, is sports-media technology and product. Jay Snowden, CEO since January 2020, is the executive who pushed the company from a regional casino operator toward media, sports betting and interactive gaming. The strategy's success or failure is, fairly, his to own.