The building still stands. One hundred and ten stories of black steel and glass still cutting the Chicago skyline. They do not call it the Sears Tower anymore. The name was sold off in 2009, a quiet surrender that barely made the news.

But the company that built it, the company that needed the tallest building in the world just to hold its ambition, is gone. At its peak, Sears had 850 stores and 350,000 employees. One out of every $100 in the American economy passed through a Sears register. They sold you your appliances, your tools, your clothes, your tires, and your insurance.
Twenty-three million people carried the Sears credit card, the biggest in retail. For most of the twentieth century, there was no second place. There was Sears, and then there was everyone else. They filed for bankruptcy owing $18 billion.
And every bit of it traces back to one decision. In 1886, a railroad station agent named Richard Sears started selling watches by mail. Within ten years, that side hustle had become the most important retail company in America. Not because of the watches, because of what came after them.
Sears figured out that millions of families across rural America were trapped. The local general store was the only option. Prices were whatever the owner decided, and there was nothing you could do about it. So Sears printed a catalog, fixed prices, money-back guarantee, delivered by mail.
By the mid-1890s, that catalog ran over 500 pages. Everything from plows to petticoats to parlor furniture, all cheaper than anything within fifty miles. For families on the prairie, it was not a sales brochure. It was an escape hatch.
And starting in 1908, you could turn to the back of the catalog and order a house. Not a blueprint, a house in a box. Twelve thousand pieces, lumber, nails, shingles, plumbing, wiring, shipped by rail, assembled by the family that bought it. Over 70,000 of those homes went up across the country.
Some of them are still lived in today, nearly a century later, with the porch lights on and the lawns mowed. Think about what Sears had built by mid-century. A catalog reaching every zip code, warehouses and shipping that could deliver in days, a credit system woven into every transaction, customer data on millions of households. That is the business model that would make Amazon the most valuable company on Earth.
Except Sears had it running sixty years earlier, with a printing press and the United States Postal Service. By the 1960s, Sears was not a store you just went to. It was a store you grew up in. Over 700 locations, and in most towns, Sears was the biggest thing in the mall, or the reason the mall existed in the first place.
You knew you were there before you walked through the doors. The parking lot alone told you, rows of station wagons and pickup trucks, a father carrying a boxed Kenmore to the tailgate with both hands. Inside, the Craftsman section had steel drawers you could pull open and feel the heft of a ratchet set that would outlive you. The Kenmore floor had washers and dryers lined up like tanks, and every one of them came with the understanding that it would still be running when your kids left for college.
DieHard batteries started cars on January mornings when nothing else would turn over. Craftsman hand tools came with a lifetime guarantee, and Sears actually honored it year after year. No receipt required, no argument. These brands were not marketing.
They were a contract between the company and the customer. And for decades, Sears kept its end. Then there was the portrait studio in the back. Every family went through it at least once.
The stiff pose, the forced smiles, the blue backdrop that showed up in every grandmother’s living room in America. And every September, the fall catalog arrived, thick as a brick, the wish book. Kids commandeered it the moment it hit the table, dog-earing pages, circling items in marker, building a case for Christmas morning one page at a time. Your parents already knew what you wanted before you said a word; the evidence was all over the catalog.
All of it ran on the Sears card. Twenty-three million households, the biggest retail credit card in the country. Every purchase tracked, every buying pattern mapped. Sears knew what American families spent, what they needed, and when they would need it again.
No other retailer had anything close to that kind of intelligence. In 1973, they put a stamp on all of it, the Sears Tower. One hundred ten stories in downtown Chicago, the tallest building on the planet. A steel and glass declaration that this company answered to no one.
But the view from the top floor can make you forget what is happening on the ground. And in 1981, the men in that tower stopped looking down. In a single week in October 1981, Sears spent nearly $800 million on two acquisitions, Dean Witter Reynolds, one of the largest stock brokerages on Wall Street, and Coldwell Banker, the biggest real estate brokerage in the country. Combined with Allstate Insurance, which they already owned, and the Discover credit card, which they would launch a few years later, the strategy was clear.
Sears wanted to be a financial services empire. Buy your socks, buy your stocks, take out a mortgage, all under the same roof. They built over 300 financial service counters inside their stores, brokerage desks wedged between the tool department and the lawnmower aisle. And almost immediately, the plan fell apart.
The in-store branches underperformed Dean Witter’s own stand-alone offices. Customers were not interested. The promised crossover, millions of Sears shoppers becoming investment clients, never materialized. Four years in, the financial centers were still losing money.
But the real price was not what the brokerage desks cost. It was what the stores lost. Every dollar and every executive hour that went into financial services was a dollar and an hour that did not go into keeping Sears the best retailer in the country. And that vacuum was about to be filled.
In 1981, the year Sears decided to become a bank, Walmart had about 300 stores. By 1990, Walmart was the number one retailer in America. Nine years. Sears had held that title for decades and lost it because they were studying balance sheets from Dean Witter instead of foot traffic in their own aisles.
And it was not just Walmart. Target moved into the space above Sears, value with better design, cleaner stores. Home Depot went after the Craftsman loyalists with deeper inventory and knowledgeable staff. Best Buy pulled the electronics and appliance customers who used to count on Kenmore.
Department by department, Sears was being outflanked by companies that were paying attention. And Sears, still running brokerage counters nobody asked for, could not see it happening. By 1992, Sears admitted the financial services experiment had failed. They unloaded Dean Witter, Coldwell Banker, eventually Allstate.
A full decade wasted, and the retail business they returned to was no longer theirs. Then came the wound that still stings the most. In 1993, Sears killed the catalog. The wish book, the foundation the entire company had been built on, was shut down.
The warehouses were closed, the distribution routes were scrapped, and they built nothing to replace it. What makes that decision even harder to understand is that Sears already saw the future coming. In the 1980s, they helped launch Prodigy, one of the first online services in America. Customers could use it to shop, read the news, send messages, even buy products from home over a computer screen.
Sears had already experimented with the basic idea behind online shopping almost a decade before Amazon existed. They had the customers, the warehouses, the delivery network, and the trust. But instead of building on that advantage, they walked away from it. One year later, Jeff Bezos started Amazon out of a garage.
Sears already had everything Amazon would spend two decades trying to build: the logistics, the reach, the customer trust. If they had moved the catalog onto a screen, the course of American retail would have had a completely different ending. Instead, they handed that future away and got nothing in return. And in 2003, they sold the credit card business.
Twenty-three million accounts and three decades of household purchase data went to Citigroup for $6 billion. The richest customer data set any retailer had ever built, gone for a one-time payout that was spent within a few years. In 2005, hedge fund manager Eddie Lampert merged Sears with Kmart, a discount chain barely out of its own bankruptcy. On a spreadsheet, it looked like scale: 5,600 stores across the country.
On the ground, it was two damaged brands propping each other up and calling it a strategy. Lampert did not invest in the stores. He extracted from them. Inside the company, he created a system that made different Sears departments compete against each other like rival businesses.
The appliance division fought the clothing division for floor space. The tool department fought for marketing money. Managers were judged against each other instead of working together. Departments that should have been helping each other started acting like enemies.
While Sears employees were busy fighting internal battles, Walmart, Target, and Home Depot were taking their customers away. Cash that should have gone into renovations went into stock buybacks. Maintenance was gutted. Staff was slashed.
Ceiling tiles went yellow. Floors cracked. Fitting rooms sat unattended. Shelves that once held the most trusted names in American retail were half empty, lit by fluorescents that buzzed and flickered.
Walking into a late-era Sears felt less like shopping and more like watching a company count down its own clock. The Craftsman brand was sold off. Kenmore was licensed out. DieHard followed.
The names that had meant something to three generations of American families were stripped away and scattered. Under Lampert, Sears Holdings lost more than $10 billion. The store count collapsed from 5,600 to barely a thousand. Over 200,000 jobs disappeared.
On October 15, 2018, Sears filed for Chapter 11 bankruptcy. $18 billion in debt. When the final clearance sales began, long-time customers walked through stores they did not recognize. Shelves stripped, lights half off.
Some of them just stood in the aisles for a moment, not buying anything. Just standing there with the look of someone who came to pay their respects. Here is what went away when Sears went away. It was not just a retailer.
It was the store where a working family could outfit an entire life under one roof. The washing machine for the new house. The tools for the garage. The coat for the kid who had outgrown last year’s.
The portrait on the wall. The catalog for Christmas. All of it on a card they would pay off a little at a time. Because the store trusted them the same way they trusted the store.
You can still buy Craftsman tools and Kenmore appliances. Different companies make them now. The names are the same. But the promise behind them, the lifetime guarantee, the no-questions replacement, the sense that someone actually stood behind what they sold, that does not exist anymore.
The labels survived. What they used to mean did not. Sears did not lose to the competition. It lost to its own executives.
In 1981, they decided that selling to American families was not enough. They wanted Wall Street margins. And by the time they gave that up, the families had found somewhere else to go. The tower still stands in Chicago under a different name.
From a distance, it looks the same. That is the thing about Sears. The structures lasted. The buildings, the tools, the houses, everything the company built with its hands survived.
Everything its executives decided with their ambition did not. Somewhere in your family, there is a Craftsman wrench that is older than most of the people reading this. It still works. The company that guaranteed it is gone.
That is the whole story, right there in your hand.