Carl Icahn is having a terrible day

Carl Icahn

(Dealbook Conference)

Monday's ugly open is turning into an especially horrible experience for billionaire investor Carl Icahn.

Icahn holds 73 million shares of Chesapeake Energy, which fell more than 50% on a news report that it had hired a team of lawyers to restructure its debt.

The stock, which has been halted, is down 64% year-to-date.

Icahn started buying commodities and energy stocks like Chesapeake in earnest last summer, growing his stake in Cheniere and buying an 8.5% stake in the miner Freeport-McMoRan.

As Business Insider's Portia Crowe pointed out last month, that hasn't worked out so well for him in general. Take those two stocks alone as an example:

• Cheniere fell 6.25% in Monday's trading and is down 35% year-to-date.

• Freeport-McMoRan is up 1.23% in Monday's trading but is down 14% for the year.

As of September, energy stocks were the third-largest sector holding in Icahn's portfolio.

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