They probably would have been fine regardless of Amazon if they hadn’t been run into the ground by a libertarian econ major.

In 2008, Sears CEO Eddie Lampert decided to restructure the company according to Rand’s principles.

Lampert broke the company into more than 30 individual units, each with its own management and each measured separately for profit and loss. The idea was to promote competition among the units, which Lampert assumed would lead to higher profits. Instead, this is what happened, as described by Mina Kimes, a reporter for Bloomberg Business:

An outspoken advocate of free-market economics and fan of the novelist Ayn Rand, he created the model because he expected the invisible hand of the market to drive better results. If the company’s leaders were told to act selfishly, he argued, they would run their divisions in a rational manner, boosting overall performance.

Instead, the divisions turned against each other — and Sears and Kmart, the overarching brands, suffered. Interviews with more than 40 former executives, many of whom sat at the highest levels of the company, paint a picture of a business that’s ravaged by infighting as its divisions battle over fewer resources.

A close-up of the debacle was described by Lynn Stuart Parramore in a Salon article from 2013:

It got crazy. Executives started undermining other units because they knew their bonuses were tied to individual unit performance. They began to focus solely on the economic performance of their unit at the expense of the overall Sears brand. One unit, Kenmore, started selling the products of other companies and placed them more prominently than Sears’ own products. Units competed for ad space in Sears’ circulars…Units were no longer incentivized to make sacrifices, like offering discounts, to get shoppers into the store.

They literally had all the pieces already in place with their catalog/mail order/warehouses.

They already screwed up however

In 1993, Sears discontinued its famous catalog to focus on in-store retail operations.

To fight off Walmart they got rid of all the shipping and things that made the catalog work in 1993 like the little outlet /pickup stores in small communities.

They focused on the physical stores and peaked in 2007 just in time for Amazon to take off. They no longer had all that distribution that gave up in 1993.

https://www.businessinsider.com/rise-and-fall-of-sears-bankruptcy-store-closings#in-the-early-2000s-kmart-acquired-sears-to-form-a-new-major-company-sears-holdings-corporation-18

Same thing happened to Blockbuster, the giants never think their day will come

They were pumped and dumped into the ground.

And the Discover card.

And being a founding partner of Prodigy...

Another example is Montgomery Ward, who were among the first to do mail order and then pivoted to department stores. You'd think they'd see the advantage of it, but they failed even before Sears.

Yeah during that time my friend tried to buy a pair of shoes in Sears, the salesperson kept pushing him to use a terminal to order online. You know, while he was standing right next to a bunch of shoes that he wanted to buy.