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“What I found astounding was here was a company with a catalogue business across the country and they somehow messed up when e-commerce was coming in. It was theirs to lose. For the longest time, Sears was the only place for young families to go. Fifty years ago, it was one of the very few places to give credit.”

Many industry analysts say the retailer’s fortunes worsened after billionaire hedge fund investor Eddie Lampert and his ESL Investments Inc. gained control of Kmart in 2003 and merged it with Sears Roebuck in 2005 to create Sears Holdings Ltd.

The following year, Sears Holdings made a bid to buy up the remaining 46 per cent stake of Sears Canada that it did not own to take the company private, but the effort failed after a dispute with minority shareholders.

It's very sad, and it's just amazing how they could fritter away their name, reputation and business model

By 2014, Sears Holdings had a 51 per cent stake that Lampert bought up directly and through ESL after he was unable to find a buyer for the Canadian business. More recently, his combined holdings with ESL stood at about 45.3 per cent.

Analysts were critical of Sears Canada’s failure to significantly reinvest in its business over the last decade even as it raised cash through hundreds of millions of dollars in asset sales by selling off its plum leases to landlords. Observers also questioned Sears Canada’s decision to issue $600 million in special dividends to its shareholders in 2012 and 2013, a move that would significantly benefit Lampert and ESL.

“The company was always saying it wanted to reinvent itself and they did try to a degree, but they didn’t spend very much money on it, and they had money from the asset sales,” said Alex Arifuzzaman, partner in Toronto-based retail real estate specialist InterStratics Consultants.