Billionaire hedge fund manager Bill Ackman revealed his stock picks for the Robin Hood Foundation’s stock-picking contest and named conglomerate Icahn Enterprises (IEP) as his short position and financial firm Fannie Mae (FNMA) as his long position, according to a post on X. The competition pits top investors against one another for charity, with the winner determined by who generates the highest profits from October 28, 2024, to April 30, 2025.
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So far, Ackman’s bets appear to be paying off. Since the start of the contest, Icahn Enterprises (IEP) has declined 34%, benefiting his short position, while Fannie Mae (FNMA) has surged 83%. The contest is designed to raise funds for the Robin Hood Foundation, which is focused on fighting poverty.
An Interesting Short Position
Ackman’s choice for his short position is actually quite funny since it is the company run by billionaire activist investor Carl Icahn. And there is no shortage of history between the two investors, as they had what was, perhaps, the most well-known feud in the financial world. Their most infamous feud dates back to 2013 when Ackman took a massive short position against nutrition company Herbalife (HLF) after claiming it was a pyramid scheme.
Icahn, on the other hand, publicly defended Herbalife by calling Ackman’s thesis misguided and eventually took a large stake in the company. Interestingly, during a heated 27-minute exchange between the two on CNBC in 2013, trading volume reportedly dropped by 20% as traders became glued to the TV. The rivalry continued for years, but Herbalife ultimately won out, as Icahn profited from his investment while Ackman closed his short position in 2018 with significant losses.
However, in an ironic twist, Icahn Enterprises stock has been struggling ever since a report from short-seller Hindenburg Research in 2023 accused it of overvaluing its assets and operating with unsustainable dividend payouts. This triggered a decline in investor confidence that led to a sharp drop in the stock price. Additionally, Icahn Enterprises has been dealing with heavy leverage, a challenging market environment, and declining performance across key segments, which are further weighing on the stock.
Is IEP a Good Stock to Buy?
Using TipRanks’ technical analysis tool, the indicators seem to point to a negative outlook. Indeed, the summary section pictured below shows that five indicators are Bullish, compared to three Neutral and 14 Bearish indicators.
