Jim Chanos, who once bet against Enron, says shorting Donald Trump's companies was a no-brainer.

"The easiest short sales I've ever had in my life were the stocks and bonds of Donald J. Trump's companies. ... It was like numerous ocean liners hitting many icebergs repeatedly," the Kynikos Associates founder said Tuesday at a Democratic Congressional Campaign Committee fundraiser in New York.



The short-seller Chanos, a large donor to Democratic causes and candidates, hosted the event, which President Barack Obama attended. Trump, the billionaire developer and Republican presidential nominee, has boasted of his business success throughout his presidential run. Democrats have repeatedly attacked Trump's record, claiming he has enriched himself without helping those he worked with over the years.

It was unclear exactly which companies from Trump's empire Chanos shorted. But Trump companies have filed for bankruptcy multiple times, and stock and bondholders for his Atlantic City casinos lost more than $1.5 billion in the 1990s, according to The New York Times.

Trump did take one company, Trump Hotels and Casino Resorts, public in 1995. People who invested in the stock endured a brutal run, according to MarketWatch.

The Trump Organization did not immediately respond to a CNBC request for comment.