The primary owner of Sears was hedge fund manager Eddie Lampert. His ESL Investments firm bought a controlling stake in Kmart following its own bankruptcy in 2003 and then merged it with Sears.
Scroll through the list of some other high-profile retail bankruptcies, and you'll notice that Sears isn't the only one that couldn't be saved by the supposedly smartest guys on Wall Street.
Many well-known retailers that ultimately succumbed to bankruptcy were loaded up with debt, making existing problems even worse.
Toys 'R' Us, which closed its doors for good this summer, was backed by private equity firms KKR and Bain Capital as well as real estate investor Vornado Realty Trust.
Bain was also the primary investor in kids' clothing retailer Gymboree, which exited bankruptcy last year but closed 350 stores as part of the reorganization.
The slow, painful death of the mall -- and many of its big tenants
Payless ShoeSource, owned by San Francisco private equity firms Blum Capital and Golden Gate Capital, went bankrupt last year and wound up closing nearly 700 stores.
But wait. There's more! RadioShack, backed by hedge fund Standard General, has gone bankrupt twice since 2015. The hedge fund arm of Wall Street firm Blackstone (BX) owns struggling New York grocery chain Fairway, which filed for bankruptcy in 2016.
The carnage doesn't end there. Private equity ownership has been particularly brutal to once-popular mall-based retailers. The Limited, Wet Seal, Claire's and Aeropostale all went bankrupt and had private equity or hedge fund backers.
And in perhaps the biggest bust of all, Sports Authority, which was bought by private equity Leonard Green & Partners in 2006, shut down for good in 2016 -- leading to the loss of about 14,500 jobs.
"Hedge funds are systematically destroying jobs across the nation," said Carrie Gleason, campaign manager for Rise Up Retail, a worker advocacy group.
"From Toys 'R' Us to Sears, these financial predators are extracting the value out of these retail establishments, forcing the closure of thousands of stores, and throwing tens of thousands of workers into the streets," Gleason added.
Failure to take online shopping threat seriously hurt many retailers too
But bloated balance sheets weren't their only problems. Poor strategies didn't help either. While Amazon (AMZN) may not have necessarily been the sole reason for the collapse of Sears, the rise of digital shopping was certainly an issue.
Some big retailers, like Walmart (WMT) and Best Buy (BBY), have built robust oniine and mobile shopping operations. But Sears and many of the others that went bankrupt failed to adapt to changing retail trends. A physical store is no longer enough.
"Brick-and-mortar retailers are fighting over an ephemeral slice of a shrinking pie," said Jack Ablin, chief investment officer with Cresset Wealth Advisors.
Ablin added that many private equity investors lack the expertise to effectively make the shift from traditional retail to online commerce and that they were also reluctant to commit more capital for the long-term to transform these struggling retailers.
Sears is the fifteenth retailer to file for bankruptcy this year, Ablin noted. It joins other high profile private equity backed casualties Toys "R" Us, shoe seller Nine West and quirky gadget retailer Brookstone.
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