Things are pretty desperate at Citi ^[1]when they trot Prince Al-Waleed out. The Journal put out the news ^[2] that the Saudi super-investor has raised his “less than 4%” stake to 5%. With a 5+ billion-share float and the stock at $6, the Prince put in less than $500 million.

Bloomberg reports that the Prince is still in the black on his Citi investment:

Alwaleed’s arrival as a celebrity investor came with the Citicorp stake, for which he paid the equivalent of $2.98 a share after adjusting for stock splits, acquisitions and spinoffs, according to Bloomberg calculations. In the decade through 2007, the stock averaged $42. Today — after more than $13 billion of loan losses and subprime-related writedowns — it’s still trading at more than twice what Alwaleed paid.

So another $500 million isn’t that much of a vote of confidence, is it?

Bloomberg ^[3] adds some depth to the explanation:

His Riyadh-based Kingdom Holding Co. has slumped 63 percent — more than Saudi Arabia’s Tadawul All-Share Index or Buffett’s Berkshire Hathaway Inc. — wiping out $13 billion in value. Kingdom Holding today said Alwaleed will increase his Citigroup stake, his largest holding, to 5 percent, even after the shares fell 77 percent since Jan. 1.

With News Corp trading in the same range as Citi, two of Al-Waleed’s most famous holdings are in a deep hole. Take a look at Berkshire Hathaway shares too. They’re down 40% in the last two months. Looks like the whales are in the same shallow pool as the rest of us.