Background
Founded in 1886, Sears was once the world’s biggest retailer and America’s largest private-sector employer. The department store’s former Chicago headquarters was even the world’s tallest building until 1996.
But since its bankruptcy filing and delisting from the Nasdaq in 2018, the company has struggled financially. As of June 2025, Sears had only eight stores left in the US—down from the roughly 4,000 stores it had at its peak in 2012.
Before Sears and its famous Sears catalog, most people had only purchased items they could touch and feel in person before buying, and they typically bought those goods from someone they knew and trusted. The Sears catalog changed that, normalizing the consumer behavior that e-commerce giants like Amazon and eBay now thrive on.
History
In 1886, Sears cofounder Richard Sears purchased a shipment of watches for a discounted price after a local merchant refused the shipment at the train station where Sears worked. Sears then sold the watches to other railroad agents for a profit.
Around the same time, two things happened in the US: The nation’s railroad system was expanding, as was the postal system. Sears and his business partner, watchmaker Alvah Roebuck, saw an opportunity for a retailer who could now deliver items to small towns nationwide.
So in 1888, Sears started mailing out a catalog where people could order watches and jewelry from the comfort of their homes. What was originally called the R.W. Sears Watch Company became Sears, Roebuck and Company in 1893 as the catalog expanded to other home goods (including the homes themselves, also known as Sears and Roebuck houses).
Although Sears became the first major American retailer to IPO (1440 Topics: Initial Public Offerings) in 1906, it didn’t open its first physical store (in Chicago) until 1925, when its president at the time, Robert Wood, accurately predicted that the rise of personal vehicles would change how Americans shopped.
Wood also helped Sears create Allstate Insurance during his tenure after suggestions that the retailer could sell auto insurance through its catalog, naming the company after a Sears tire brand.
In 1984, alongside IBM and CBS, Sears created an internet service provider called Prodigy with ambitions to facilitate a platform for retail sales. Learn more about Prodigy’s other functions outside of retail—and why it ultimately wasn’t much of a success—here.
Soon after, in 1986, a Sears subsidiary launched the credit card brand Discover via a Super Bowl commercial. For more details about Sears’ history, scroll through this timeline.
Bankruptcy
Some argue that Sears’ financial decline began in the 1990s after the retailer sank a significant amount of money into the aforementioned Prodigy tech product (to little financial success) and stopped publishing its catalog in 1993. Sears also struggled to compete with up-and-coming discount chains like Walmart and, later, Amazon.
In 2005, Kmart owner and hedge fund manager Eddie Lampert purchased Sears, merging the two stores and dropping “and Roebuck” from the brand’s name. Lampert restructured the company into a series of complex divisions, sold off Sears brands such as Craftsman and DieHard, and closed hundreds of stores in an effort to make it an “asset-light” business. While Sears was losing money, more tech-savvy competitors like Amazon were growing rapidly.
Sears filed for Chapter 11 bankruptcy (1440 Topics: Bankruptcy) in October 2018. Eddie Lampert stepped down as CEO soon after.
Future
As of this writing, Sears is owned by Transformco, a holding company formed in 2019 to purchase some of the Sears assets after the retailer’s 2018 bankruptcy.
With few physical stores left, some argue that Sears’ future depends on its online store, Sears.com, as well as its appliance repair and installation business. Sears is no longer a public company and does not report its financials, making its current valuation difficult to determine.
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