Since I find that some short sellers do excellent in-depth research, I run a short-selling contest each September. DeFilippo's win DeFilippo won the 2016-2017 contest with a 37.1 percent gain in Sears Holdings Corp. (SHLD) — which means that the stock fell 37.1 percent after taking dividends into account. A year ago, DeFilippo noted that Sears had lots of debt, that its cash hoard was low and that its sales were declining. Sales have continued to decline in the four quarters since he made his pick. The Pittsburgh accountant had won the 2015-2016 contest by shorting C&J Energy Services (CJES), producing a 91 percent gain (on paper, since the contest doesn't require participants to actually sell short in the real world). For the 2017-2018 contest, DeFilippo says he will probably sell short Simon Property Group Inc. (SPG). "Every week, you read about some big department store chain closing stores," he says. As a landlord to many major chains, Simon is vulnerable, he believes.