Other hedge fund tycoons buy helicopters. John Henry used his money to end the Curse of the Bambino. How big can you get?

But that moment in the fall of 2004 when the Red Sox won it all proved to be the pinnacle of his success. Since then, his investment fortunes have been in an increasingly desperate slide.

How bad does it look? You can see the figures at Henry's own Web site, and they are astonishing. Since December 2004, his main investment fund has lost a stunning 36%. And according to a report in the May 29 Wall Street Journal Henry's slide continues, as Merrill Lynch has redeemed $600 million from the firm.

While a simple index fund over that period would have turned each $10,000 into about $12,450, Henry's "Strategic Allocation" fund has turned the same amount of money into a mere $6,360. Except we're not actually talking $10,000. We're talking hundreds of millions of dollars.

No wonder his company's assets under management are in free fall as clients yank out what money they have left. In three years, assets have more than halved from $2.9 billion to just $1.2 billion by the end of April. And the latest annual report reveals that half of Henry's clients have now actually lost money investing with him over the long term.

The company declined to comment.

The bottom line?

Henry had disastrous back-to-back years in 2005 and 2006 and his magic touch seems to have deserted him. He's been caught on the wrong side of trade after trade. Mark Rzepezynski, his long-standing chief investment officer, finally left in a shake-up over the winter. It hasn't helped yet. The main investment fund, Strategic Allocation, has already lost another 9.5% so far this year.

If you liked this article you might like

European Central Banks Blew It With Gold

European Central Banks Blew It With Gold

Bookies: Thompson Out, Rudy and Mitt Tops

Bookies: Thompson Out, Rudy and Mitt Tops

$1,000 Google? Sure, but Why Bother?

$1,000 Google? Sure, but Why Bother?

Nothing Constant at Fidelity but Change

Nothing Constant at Fidelity but Change

Citi's Fat Cats Take a Drubbing in Decline

Citi's Fat Cats Take a Drubbing in Decline