NEW YORK ( TheStreet) -- They say the house always wins in a casino, but investors in shares of Caesars Entertainment Group (CZR) will almost certainly be losers, said George Schultze, CEO of Schultze Asset Management.

"The interesting story behind Caesar's Entertainment Group is that shareholders almost never get any recovery when a company goes bankrupt in the United States," said Schultze, who is short the stock which has fallen nearly 50% in the past year. "This company entered bankruptcy in January, the stock is over $9 a share, and eventually it too will be wiped out."

Schultze reminded investors that the gaming company was one of the biggest leveraged buyouts in the casino space and has over $13 billion in debt it cannot service. And while over a quarter of the company's shares are currently being sold short, creating something of a buffer in the stock because shortsellers will inevitably be forced to cover, Schultze said eventually the shareholders will lose out.

"The junior debt of this company, which is senior to the equity we are shorting, trades at just pennies on the dollar right now," said Schultze.

Meanwhile, Schultze is also betting against Diana Shipping (DSX), saying the dry bulk cargo shipper is in a troubled industry that is "very much under water".

"There was a massive ship-building boom a couple years ago, and now the shipping companies are paying the consequences," said Schultze. "You have far too many ships and that has caused the Baltic Dry Index to collapse to a thirty-year low." Shares of Diana are down 44% in the past year although the short percentage of the float is only 4%.

If you liked this article you might like

Bonderman's Controversial Remarks at Uber Puts His Other Five Seats at Risk

Analysts' Actions -- Box, Caesar's, Goodyear, Idexx Labs and More

Caesers on the Brink of Exiting Bankruptcy

Caesars Entertainment Reprices $2.4 Billion Loan