But Erin Gibbs, who manages $12 billion in assets for S&P Investment Advisory, said a few of these stocks actually look like attractive buys, specifically GameStop and Nordstrom which are included in her model portfolios.
"I completely disagree with the shorts on both of those stocks," she said Wednesday on CNBC's "Trading Nation." "Fundamentally these stocks look really good, both from a cash flow basis and [in] valuation."
According to Gibbs, GameStop has seen a substantial fall in the percentage of shorts in the past two weeks, as investors start to "take some money off the table." Gibbs said that Nordstrom has also started to see short bets winding down as the stock has soared this year.
Read MoreMarket calm has eerie parallels to pre-swoon August
Five out of the top seven stocks with the highest short interest have risen this year. But the bets against two energy stocks, Chesapeake Energy and Transocean, seem to be paying off. Chesapeake has fallen 9 percent in 2016, and Transocean has plunged 25 percent in the same time.
And Todd Gordon of TradingAnalysis.com said there looks to be even more pain ahead for the worst-performing of the bunch.
The chart of Transocean "is technically a beautiful-looking disaster," he said Wednesday on "Trading Nation."
From a technical perspective, Gordon said Transocean's stock remains below its 200-day moving average and trapped in a downtrend channel. With crude oil also falling back below $40 a barrel, "this doesn't look good for the outlook for the stock," he concluded.