Bill Ackman leads a prestigious Robin Hood Foundation stock-picking contest with a 112.5% return, primarily due to his short position on Carl Icahn's holding company, Icahn Enterprises (NASDAQ: IEP). This strategic move, while not directly targeting Caesars Entertainment, has benefited from IEP's recent 19% decline.

The contest, running from October 28 to April, requires participants to donate $10,000 and make two stock picks - one long and one short. Ackman's performance significantly outpaces the second-place contestant, who achieved a 63.1% return.

While Icahn recently acquired a 2.44 million share position in Caesars Entertainment, Ackman's contest strategy isn't aimed at the casino operator directly. Icahn's history with Caesars includes orchestrating the $17.3 billion Eldorado Resorts acquisition in 2019.

The Ackman-Icahn rivalry dates back to 2013, centered around Herbalife investments, though the two reconciled in 2014. Notable gaming industry investors participating in the contest include:

• Michael Fitzsimmons (Eminence Capital): Selected Melco Resorts (NASDAQ: MLCO) as a long position
• David Einhorn (Greenlight Capital): Penn Entertainment (NASDAQ: PENN) shareholder
• Rickey Sandler (Eminence Capital): Activist investor in Entain Plc (OTC: GMVHF)

The Robin Hood Foundation, dedicated to fighting poverty in New York City, has attracted top finance industry figures to this charitable competition, highlighting the intersection of philanthropy and investment expertise.

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