Where does a business handcuffed by a covenant that caps debt at 7.5 times cash flow go when it needs more money? If it's Las Vegas Sands (NYSE: LVS), it reaches into the bulging pockets of major shareholder and chairman Sheldon Adelson. According to The Wall Street Journal, Adelson has loaned Las Vegas Sands almost half a billion dollars.

The move will allow the company to remain within the covenant of its current $5 billion facility, which is crucial as it looks to raise an additional $2 billion for ongoing projects and refinance a current $3.3 billion loan. Earlier this month, S&P lowered the company's credit rating to B+ from BB-, reflecting weakness in the gaming industry and illiquidity in the company's position.

Traditionally, the large casino-based companies have looked to investment banks for project financing (ouch!) and LVS continues to press forward on plans to build not just in Macau, but other Far East markets such as Singapore and perhaps Taiwan. Even before the current tight money climate in the U.S., though, LVS and other major players in the Far East casino development business have been looking overseas for financing.

Finding that funding has been made more difficult by less than stellar returns from Macau (see Sand Macau's revenues were down 30% in the second quarter) and malaise in Las Vegas, where slot income was down a billion dollars last year.

The company's stock has been on an appalling downward slide since September of 2007, when it peaked at over $140 a share. It has tumbled another $4 today, to under $33 a share. It appears that investors aren't heartened that Las Vegas Sands had to tap its own major stockholder for funding. The stock drop has sucked even more of Adelson's money out of his pocket.

I suspect Las Vegas Sands will need some good news, such as increased revenues, before investors will be eager to once again roll the dice on its shares.