Betting against dying malls is easier said than done. Though the properties may be struggling, they can take a while to fail, resulting in a rather costly upfront and long-term investment.

Despite the risks, Alder Hill Management hedge fund manager Eric Yip believes he is up to the task. The firm has made a series of bets against commercial mortgaged-backed securities anchored to malls originated in 2012, and while the targeted indexes have declined by nearly 10%, some investors are worried any serious payout is still far off, Bloomberg reports.

Betting against these malls requires a hefty investment up front and regular payments to hold the position, so while most experts agree it is better to be bearish than bullish on the retail sector, if it takes too long for malls to fail, the bets will become too expensive to maintain.

Almost all of the second-tier malls in the Market CMBX 6 index (which references 25 bonds from a portfolio of 25 CMBS loans issued in 2012) need to liquidate within the next year or two for the trade to generate a reasonable return, AllianceBernstein director of commercial real estate credit research Brian Phillips said.

While malls are undoubtedly a weak link, Phillips said it is not likely the REITs and insurance companies that own these mortgages will allow them to all fail at once. So while shorting dying malls is a sound idea in theory, the expense of maintaining the position and the necessity of getting the timing right makes it a hard bet to win.