Carl Icahn's energy bets are backfiring

The price of oil continues to hit new lows, and it's taking a toll on some hedge fund managers that have made big bets on the energy industry.

Billionaire hedge fund manager Carl Icahn's energy bets are backfiring spectacularly.

Icahn invested in liquid natural gas companies Cheniere Energy and Freeport LNG in August and September of 2015.

Both have dropped significantly in price since.

Freeport is down 56.5% since Icahn's investment, while Cheniere is down 50.6%.

Icahn has a history of poorly-timed energy bets.

In October 2014, Icahn took a stake in Canadian energy company Talisman. The company's stock then cratered 71% before he was able to unload it in December 2014.

Energy was Icahn's third-largest sector holding as of September 2015, according to an investor presentation published on Icahn Enterprises' website:

Brent crude oil, the international benchmark, fell below $29 at one point on Friday.

Carl Icahn said in an interview December that the oil price could fall further because it started to pick up again.

"I don't think anybody thought it would be this bad because you obviously have the Middle East, Saudi Arabia just keep pumping and pumping and pumping oil," he said. "And that's a secular change that you can't do anything about. It's a political thing also."

"I think it will, it could very easily get worse. And eventually, I think it will get better, but it could get worse," he added.

We've reached out to Icahn Enterprises for comment and will update if we hear back.