The Risks with Short Straddles Looking at an at-expiration diagram or even analyzing the gamma/theta relationship of a short straddle may sometimes lead to a false sense of comfort. Sometimes it looks as if short straddles need a pretty big move to lose a lot of money. So why are they definitely among the riskiest strategies to trade? That is a matter of perspective. Option trading is about risk management. Dealing with a proverbial train wreck every once in a while is part of the game. But the big disasters can end one’s trading career in an instant. Because of its potential—albeit sometimes small potential—for a colossal blowup, the short straddle is, indeed, one of the riskiest positions one can trade. That said, it has a place in the arsenal of option strategies for speculative traders.