I'm starting this thread in hopes of generating specific stories of "legendary" trades of which the writer has personal knowledge. I'll start with my own: While trading with Tim Sykes in 1999, I traded a joint account for Tim and myself. At the time I turned the account over to the firm to concentrate on my own trading, we had a small position of 19,000 ENN (Equity Inns), which was under water by about $20k. A few months later I learned that Tim had "added to the position in ENN." I believe his exact words were,"I bought a little more." A week later I learned that "a little more" was 1,000,000 shares. It seems 'adding to a loser' does work sometimes. After the stock had rallied $2-3 dollars, Tim told me he had lightened up on his position. Each week, Tim told me he was 'lightening up.' After about two months of lightening up, I found out he was down to ONLY 986,000 shares!! I think he's collected about a 13% dividend during the whole time he's owned it, on top of the capital gains. I'm not sure if he still has a position.