
Bill Ackman Leads Robin Hood Contest with Strategic Short Against Icahn Enterprises
Bill Ackman currently leads a prestigious stock-picking contest for the Robin Hood Foundation, partly due to his short position on Carl Icahn's investment company, which has indirect ties to Caesars Entertainment.

Business man, stern crossed arms
Ackman revealed his short position on Icahn Enterprises (NASDAQ: IEP) in a now-deleted X post, emphasizing this was solely for the contest purposes. The competition, organized by the Robin Hood Foundation to combat poverty in New York City, requires participants to make one long and one short stock pick, with a $10,000 donation entry fee.
As of December 11, Ackman's picks have generated an impressive 112.5% return, significantly outperforming the second-place contestant's 63.1% gain. While Ackman isn't directly betting against Caesars, IEP's recent 19% decline has been partially influenced by Caesars' 5.83% drop over the past month.
The Ackman-Icahn rivalry dates back to 2013, centered around Herbalife stock positions, though they reconciled in 2014. Regarding Caesars, Icahn currently holds a 2.44 million share position, acquired in May 2024. This follows his previous involvement in orchestrating the $17.3 billion Eldorado Resorts acquisition of Caesars in 2019.
Other notable participants in the contest include:
- Michael Fitzsimmons (Eminence Capital): Long position in Melco Resorts
- David Einhorn (Greenlight Capital): Penn Entertainment shareholder
- Rickey Sandler (Eminence Capital): Entain Plc activist investor
The contest runs through April 2025, with participants representing various sectors including gaming, financial services, and healthcare.
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