Kmart was once rescued from bankruptcy by Eddie Lampert. It's unclear whether it will happen again.

Here's how Kmart went from beating Target and Walmart to twice-bankrupt in forty years
Here's how Kmart went from beating Target and Walmart to twice-bankrupt in forty years
Key Points
  • Kmart first filed for bankruptcy in 2002, then the third-largest such filing.
  • The retailer emerged under the ownership of Eddie Lampert, who later merged Kmart with Sears.
  • The new company, Sears Holdings, filed for bankruptcy two months ago. Lampert is once again trying to buy the company, thereby potentially saving both Sears and Kmart.

Much has changed in retail over the past 16 years. Amazon has risen and towering giants like Toys R Us have fallen. Kmart, though, finds itself exactly where it was in 2002: bankrupt and looking for a savior.

The discount store filed for bankruptcy for the first time in January 2002, the result of a heavy debt-load, management missteps and crushing competition from Target and Walmart. It was saved, though, by hedge fund guru Eddie Lampert, who saw in the retailer valuable real estate and opportunity for revival. He bought the bankrupt company's debt through his hedge fund ESL Investments, paving the way for him to become its owner once it emerged.

Lampert soon merged Kmart with Sears, Roebuck & Co, creating a new giant Sears Holdings. The combined company faced its own challenges. Some were new, like the rise of Amazon and decline of the mall, where many Sears stores were located. Others were the same: a heavy debt load, management missteps and crushing competition from Walmart and Target.

On Oct. 15, 2018, Sears Holding filed for bankruptcy, bringing Kmart along with it. Sales at Kmart had fallen from $31 billion in fiscal 2004 to $5.8 billion in 2018. Its U.S. store count fell from 1,511 to fewer than 750.

Once again, Kmart's fate — and perhaps its best shot at survival − is in Lampert's hands. Lampert, who is Sears' chairman, has proposed buying Sears for $4.6 billion. Doing so would save Kmart, Sears and roughly 50,000 jobs.

But the challenges Lampert faces are steeper than 16 years ago. Some Sears' creditors have urged it to liquidate. They have also expressed wariness about selling the business back to Lampert, under whom its last profitable year was in 2010. Meantime, as Kmart has languished, Walmart, Target and Amazon have poured money into their brands and technology, making it harder for Kmart to make a case it needs to exist.

Lampert, through his hedge fund, has publicly maintained his optimism in the combined company, pointing out in a statement its "immense potential to evolve and operate profitably as a going concern." Whether that optimism will create a future as it did in more than a decade ago is yet to be seen.