Donald Trump's casino group is expected to file for bankruptcy, the Wall Street Journal said, less than two weeks before the new Celebrity Apprentice starts. This is among Trump's most embarrassing failures.

And that's saying a lot.

Trump is no stranger to bankruptcy. Tuesday's expected Chapter 11 filing will be the third time the casino group — just that one Trump division, among several — has gone bankrupt. But this time is especially humiliating because this is the same company that went bankrupt in November 2004, in the midst of the fourth season of The Apprentice, the reality show in which Trump "fires" people who don't meet his business standards of constant failure and mammoth debt accumulation.

It is also the same company that was purportedly turned around by the besuited loudmouth and his partners by 2005, near the height of the Apprentice juggernaut, when it victoriously emerged from bankruptcy, for the second time.

Then late last year the company put off paying interest on its bonds, and earlier this year missed a $53 million payment, according to the Journal. Trump claims he wants to fix everything and offered to buy the company, but the bondholders are expected to seek involuntary bankruptcy, so he and Ivanka resigned the board.

In response to the bankruptcy, fellow upward failer and NBC entertainment bigwig Ben Silverman, who did a "tremendous job" by signing Trump for a second Celebrity Apprentice season, is expected to go skiing, then ask Jay Leno to move his show to 9 pm.