Sears Survived Two World Wars. It’s Now Officially Dead.

The End of a Shopping Empire

In 1886, a railroad agent in Minnesota started selling watches to make extra money.

That side hustle became Sears, Roebuck and Company, which grew into the largest retailer America had ever seen.

The company built the world’s tallest building, created brands like Craftsman and Kenmore, and even sold 75,000 houses through the mail.

Now, after 139 years, Sears is down to five stores. A former executive recently told CNN the shelves are nearly empty, and this holiday season will probably be its last.

A Watch Salesman Starts an Empire

Richard Sears was working as a railroad station agent in Minnesota in 1886 when a local jeweler refused a shipment of watches.

Sears bought them himself and started selling them to other station agents along the rail line. He made enough money to quit his job and move to Chicago, where he hired a watchmaker named Alvah Roebuck.

By 1893, the two had incorporated Sears, Roebuck and Company. They started with watches and jewelry, but Sears had bigger plans.

He wanted to sell everything Americans needed, and he figured out how to reach them.

The Catalog That Changed America

Before Sears, rural families had few options. Local general stores charged high prices and offered limited selection.

The Sears catalog changed that. By 1894, it had grown to 322 pages featuring sewing machines, bicycles, and sporting goods.

A year later, it hit 532 pages. Farm families could suddenly buy the same goods as city dwellers at published prices.

The catalog became so important that many households kept it next to the Bible. For Black families in the Jim Crow South, it meant shopping without facing discrimination.

Sears Sold 75,000 Houses by Mail

Starting in 1908, Sears offered something no one expected: entire houses shipped by railroad car.

The Modern Homes catalog featured dozens of styles, from small cottages priced at $360 to grand homes costing over $5,000.

Each kit included pre-cut lumber, shingles, nails, and detailed instructions. A homeowner could assemble one in about 90 days.

Sears sold roughly 75,000 kit homes before ending the program in 1940.

Thousands still stand across the Midwest, and some owners only discover their home’s origins when they find stamped lumber or shipping labels behind the walls.

Brands That Became Household Names

Sears didn’t just sell products. It created brands that defined quality for generations.

Craftsman tools arrived in 1927 with a lifetime warranty that meant you could walk into any Sears store with a broken wrench and walk out with a new one.

Kenmore appliances launched the same year. These brands built trust that lasted decades, even as the company that created them fell apart.

DieHard batteries became synonymous with reliability. In 1931, Sears founded Allstate Insurance and put sales booths right inside its stores.

The World’s Tallest Building

By 1969, Sears employed about 350,000 people and needed a headquarters to match its ambitions. The company hired architects to design what would become the Sears Tower in Chicago.

When construction finished in 1973, the 110-story building stood 1,454 feet tall, surpassing the World Trade Center as the world’s tallest. It held that title for nearly 25 years.

The tower was a monument to what Sears had become: the largest retailer on Earth. The company sold the building in 1988, and it was renamed Willis Tower in 2009.

Most Chicagoans still call it the Sears Tower.

Walmart and Target Start Winning

The seeds of Sears’ decline were planted in 1962, the same year three discount retailers opened their first stores: Walmart, Target, and Kmart.

These chains offered lower prices and faster shopping experiences. By 1991, Walmart had passed Sears as America’s largest retailer.

Sears never recovered.

Through the 1970s and 1980s, they expanded aggressively while Sears diversified into financial services and real estate instead of improving its stores.

The company that invented modern retail had missed the shift to discount shopping, and a new threat was already forming online.

Eddie Lampert Buys a Dying Giant

In 2005, hedge fund manager Eddie Lampert engineered an $11 billion deal to merge Kmart with Sears.

Business magazines called him the next Warren Buffett. The combined company had 3,500 stores and more than 300,000 employees.

But Lampert ran the business from his home in Florida, communicating mainly through conference calls. Instead of investing in stores, he cut costs relentlessly.

Former employees described locations with handwritten signs and barren shelves.

The Brands Get Sold Off

As losses mounted, Lampert started selling the brands Sears had spent decades building. In 2017, he sold Craftsman to Stanley Black & Decker for $900 million.

The deal let Sears keep selling Craftsman products. In 2019, after Sears had already filed for bankruptcy, the company sold DieHard to Advance Auto Parts for $200 million.

Kenmore appliances stayed with what remained of Sears, but the brand had lost its exclusive home. The names survived.

The company that created them was disappearing.

Bankruptcy and the Final Collapse

On October 15, 2018, Sears Holdings filed for Chapter 11 bankruptcy with $11 billion in debt.

Lampert stepped down as CEO but remained chairman and made a $5.2 billion bid to buy the company out of bankruptcy.

A federal judge approved the deal in February 2019, allowing about 425 stores to stay open and saving roughly 45,000 jobs.

But stores kept closing. The last full-size Kmart in the continental United States shut down in late 2024.

By the end of 2025, Sears had shrunk to just five locations in Massachusetts, California, Texas, Florida, and Puerto Rico.

What Killed the Company

Experts point to many causes: the debt Lampert took on to buy Sears, years of neglecting stores while competitors modernized, the rise of Amazon and online shopping, and a management style that prioritized financial engineering over retail basics.

Some say Lampert treated Sears like an investment to be harvested rather than a business to be grown.

He sold off real estate, bought back stock, and extracted value. Others blame decisions made decades earlier, when Sears chased financial services.

The truth is probably all of it.

Empty Shelves and Locked Doors

Mark Cohen, a former Sears executive, recently described what’s left of the company. Someone unlocks the door in the morning and locks it at night, he said, but there’s nothing to sell inside.

The five remaining stores operate in a retail world where Walmart has 5,200 locations and Amazon delivers to your door in hours.

Sears built the infrastructure that let rural America join the consumer economy.

It created brands that lasted generations and a tower that still defines Chicago’s skyline. After 139 years, the company that taught America how to shop is about to close for good.

This article was created with AI assistance and human editing.

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