With the resurgence of Vegas and the newfound popularity of poker, you'd think that just about any resort that spreads a card game is bound to be raking in the bucks. And after all the publicity it received in General Electric's (NYSE:GE) The Apprentice and the poker movie Rounders, you might think Trump Hotels & Casino Resorts' (NYSE:DJT) Taj Mahal would rank near the top of that list. Yeah, uh, think again. The Donald's gaming business, which includes three Atlantic City hotels and an Indiana riverboat casino, has been on life support for months, and last night it revealed plans to file bankruptcy next month.

The plan, which involves ceding control of Trump Hotels to DLJ Merchant Banking, a private equity subsidiary of Credit Suisse (NYSE:CSR), is the culmination of one first announced in February. The company says it will file bankruptcy papers next month, receiving $400 million then, mostly for recapitalizing debt. Trump Hotels' total obligations would drop from today's roughly $1.8 billion to $1.25 billion, with the interest rate reduced from 12% to an estimated 7.9%. That would deliver $110 million in savings annually.

I admire Trump's ability to pull off this deal. As Fool colleague Bill Mann reported, his job effectively meant convincing investors that defaulting on his company's existing obligations wasn't all that bad. Talk about selling ice to Eskimos.

Still, Trump has proven to be little more than a chump with a passable comb-over in the casino business overall. Even the best makeup artist can't disguise the fact that as CEO, he has destroyed hundreds of millions in shareholder value over the past decade. And, finally, he's paying the price.

No, no one has actually fired Trump, but published reports say he will remain on Trump Hotels' board as chairman, with his equity stake reduced to roughly 25%. Currently, he is chairman, CEO, and president, and it was expected that he'd retain the CEO title following the recapitalization. Although not exactly an embarrassing televised taxi confessional through downtown Manhattan, it's a chink in The Donald's once-invulnerable armor, and probably a good thing for long-suffering investors.

For more Fool coverage of Trump Hotels:

  • Jeff Hwang reports that Trump Hotels is nearly out of options.
  • Seth Jayson says that many of The Donald's business lessons are financial folly.
  • W.D. Crotty finds Trump Hotels' annual report to be a frightening read.
  • Bill Mann shows that the recapitalization deal might only be a short-term fix to a long-term problem.

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Fool contributor Tim Beyers aspires to see the inside of Trump's Taj Mahal poker room someday. That is, if its debt problems don't sink the casino first. Tim owns no interest in any of the companies mentioned, and you can view his Fool profile here.