Sears started off as a mail-order catalog company selling watches and jewelry in 1888. It became the largest catalog company in the United States after expanding its assortment.
In the 1920s, as catalog shopping started to fade out, Sears adapted to the changing times and opened stores. According to Investopedia, sales at its stores outpaced catalog sales by 1931.
Source: Investopedia
The company grew from being only a retailer to offering financial services, including setting up an insurance arm with Allstate and acquiring various financial brokerage firms.
It also began rolling out its own brands such as Craftsman, DieHard, and Kenmore.
Its dominance in the retail sector began to fade in the 1970s as lower-priced stores such as Target, Kmart, and Walmart gained momentum. By 1991, Walmart had taken Sears' place as the largest retailer in the country.
Source: Business Insider
Over the course of the 1990s, Sears started shedding its financial and insurance businesses and discontinued the catalog.
In 2003, Sears sold its credit-card business to Citigroup in order to focus exclusively on retail. The credit-card business had outgrown the core retail operation and accounted for 60% of its annual profits at the time.
Source: The New York Times
The chain was increasingly coming under pressure as shopping shifted online, and it failed to adapt. In 2004, Sears bought low-cost store Kmart in an effort to compete with rival chains such as Target and Walmart, which were dominating American retail.
Source: CNN Money
The deal was masterminded by Lampert, who was chairman of Kmart at the time and owned a 50% stake in its business through his ESL Investments hedge fund. He was also the largest shareholder in Sears at the time, with a 15% stake.
Lampert then became chairman of Sears Holdings, the combined company.
In 2004, BusinessWeek speculated that Lampert would become the next Warren Buffett.
In 2013, Lampert became CEO of Sears Holdings.
The company's revenue declined substantially from $36.2 billion in fiscal 2013 to $25.1 billion in fiscal 2015.
In 2016, 24/7 Wall St reported that Lampert was the most hated CEO in the US, based on ratings and employee satisfaction reviews from Glassdoor.
As sales continued to fall, Sears started to shut down stores, sell real estate, and spin off brands.
Lampert thought he could turn around both companies by cutting costs and selling the real estate where underperforming stores were located.
In interviews with Business Insider's Hayley Peterson in 2016, employees blamed Lampert for the downfall of the company.
They said that Lampert rarely spent time at its headquarters.
Lampert stopped investing in stores. "He refuses to put a dime in updating stores," one former vice president told Business Insider in 2017.
Stores were severely understaffed, with some operating on less than half of the employees they needed, workers said.
Instead, he banked on Shop Your Way, a rewards program that enabled frequent buyers to accumulate points for their purchases and turn them into coupons and discounts. This complicated program backfired as it created massive lines at checkouts and angered customers.
Several high-level executives left the company.
"There are so many people running for the door not just because the ship is sinking, but because the captain of the ship is screaming at them, blaming it on them, and telling them it's their fault," one former vice president told Business Insider in January 2017.
Hundreds of stores closed. Between 2013 and this September, its store count dropped from 1,980 to 866.
Source: Business Insider
Lampert kept the company afloat by bailing it out with billions of dollars of loans from his hedge fund ESL Investments.
The Wall Street Journal reported on Tuesday that Sears had hired advisors to help the company prepare for bankruptcy in advance of a massive debt repayment due next Monday.
Sources familiar with the matter told The Journal that Lampert isn't planning to lend the company money to make Monday's payment.
However, according to Reuters, Lampert is considering a bid for some of the company's businesses and real estate once it files for bankruptcy.
A bankruptcy filing could be imminent.
"The prognosis is gloomy, just as it has been for many years," Neil Saunders, managing director of GlobalData Retail, wrote in a note to clients on Thursday morning.
"Sears has been expert in restructuring and playing for time with various financial machinations. However, at some point, the music has to stop. We believe that time is now."