Paul Tudor Jones II--and his friend Robert Prechter, of Elliott Theory fame--famously called the crash of 1987. It burnished their images, that's for sure. Jones of course went on to have a great 1987 (a 200 percent gain that year) and has been an icon of the hedge fund world ever since. Right now, according to the New York Times, he's struggling through a not-so-great year, but at least publicly, he is not predicting another stock market crash. Prechter on the other hand is not only suggesting a big crash is on the offing but an actual depression as well. Yikes. Tidbit: "Trader," the 1980s documentary about Jones, goes for nearly $300 on the Internet.  

For more:
- here's the New York Times article