It's possible, but almost inevitably, the "strategy" employed backfires, and the trader loses everything. One that comes to mind is Brian Hunter[1], formerly of the now defunct Amaranth Advisors hedge fund. Hunter was viewed as a sort of wunderkind, but he had a natural gas position (I've heard the initial position was between $1B and $2B, but I don't know specifics) go south, and rather than sell off and accept the losses, he doubled down and sank the firm. Margin calls ensued (of up to $6B) that could not be met and assets ended up being sold off for pennies on the dollar. (I previously worked for a firm that bought a large chunk of Amaranth's assets).
Ya man I been in the industry a long time I remember Brian Hunter from even before Amaranth. Always interesting reading when his name pops up. Clearly, a brilliant trader on a different level than most guys, but ya that's not always enough on it's own. He should have gotten that DB bonus though, that story was fucked up.
[1] https://en.wikipedia.org/wiki/Brian_Hunter_(trader)