Penn Entertainment: The Largest US Casino Operator by Property Count and How They Got That Way

Penn Entertainment operates 40+ casinos — the most by property count of any US operator. The company started as a Pennsylvania horse racetrack and grew through aggressive M&A.

Penn Entertainment is the largest US casino operator by property count. Most casual gamblers don't recognize the corporate name. The brand portfolio (Hollywood Casino in particular) is recognizable; the parent company isn't.

Penn Entertainment was founded in 1972 as Penn National Race Course in Grantville, PA — a Thoroughbred horse racing facility. For 25 years it was just a racetrack.

In 1997 Penn began acquiring casino-style gambling operations. The aggressive M&A strategy that built Penn into a national operator started here.

In 2018 Penn agreed to acquire Pinnacle Entertainment for $2.8B. The deal added 12 properties to Penn's portfolio. After FTC-mandated divestitures, Penn ended up with most of Pinnacle's value while Boyd took the divested properties (Ameristar Kansas City, Ameristar St. Charles).

This is when Penn became a true national operator. By 2019 they had 40+ properties.

In January 2020 Penn paid $163M for a 36% stake in Barstool Sports — and a path to acquire the rest over time. The deal was meant to leverage Barstool's audience for sports betting.

In February 2023 Penn paid $388M to acquire the remaining Barstool stake.

Six months later (August 2023), Penn sold Barstool back to its founder Dave Portnoy for $1 — yes, one dollar.

The reason: Penn pivoted to a partnership with ESPN to launch ESPN Bet, which Penn judged more valuable than continued Barstool ownership. Total Barstool transaction cost to Penn: ~$551M. The "$1 sale" let Portnoy get his company back at terms that allowed Penn to exit cleanly.

Penn's ESPN partnership launched ESPN Bet in November 2023. Terms:

• 10-year exclusive deal
• $150M annual marketing commitment
• Penn pays ESPN $1.5B over the deal term
• ESPN Bet integrates into Penn's mychoice rewards

The deal positioned Penn as one of the major sports-betting operators alongside DraftKings, FanDuel, and Caesars. Early ESPN Bet market share has been smaller than projected, but the brand recognition is established.

40+ properties under various brands:

• Hollywood Casino Lawrenceburg (IN)
• Hollywood Casino Joliet (IL)
• Hollywood Casino St. Louis (MO)
• Hollywood Casino Aurora (IL)
• Hollywood Casino at Penn National Race Course (PA)
• Hollywood Casino Bay St. Louis (MS)
• ~10 more

• Argosy Casino Hotel & Spa Riverside (MO)
• Argosy Casino Alton (IL)

• Charles Town Races (WV)
• Boomtown (LA, NV, MS)
• Cactus Petes (NV)
• M Resort (Henderson, NV)

Three things:

1. Property breadth over depth. Penn doesn't have a single flagship destination property. They operate 40+ functional regional casinos. The strategy is volume + cross-property loyalty rather than singular destination experiences.

1. Brand inconsistency. Penn properties have multiple brands (Hollywood Casino, Argosy, M Resort). The marketing efficiency is lower than single-brand operators.

1. Sports-betting focus. The ESPN Bet partnership is more important to Penn's strategy than to Caesars (which has its own Caesars Sportsbook brand) or MGM (which has BetMGM with strong existing presence).

For mychoice rewards regulars: yes. The loyalty network covers 40+ properties — strongest cross-property reach of any operator outside Caesars.

For destination travelers: probably not. Penn's properties are functional regional casinos, not destination resorts.

For sports bettors: yes, ESPN Bet has competitive promotions in its launch markets and the integration with mychoice rewards is real.

For our take on the broader Caesars / MGM / Hard Rock loyalty competition: three-way loyalty battle.

Topics

• penn-entertainment
• hollywood-casino
• industry

More casino guides