When a jeweler declined to accept an order of watches, Richard Warren Sears saw an opportunity. He bought the watches for a good price and promptly sold them at a price that turned a tidy profit. In 1886, he founded his mail-order business R.W. Sears Watch Company.¹ After he met watch repairman Alvah Curtis Roebuck, the two moved from Minneapolis to Chicago and set up business. After selling this business and moving away for a few years, Sears returned to Chicago and again teamed up with Roebuck to start a mail-order watch and jewelry business and called it Sears, Roebuck, & Co.

Roebuck left the firm a few years later and his share of the company were bought by Aaron Nusbaum and Julius Rosenwald. Soon, Sears and Rosenwald bought out Nusbaum and took the company public in November 1906 and were given the ticker symbol S.² The company grew and increased the number and variety of products for sale. When they needed bigger quarters, they built the Sears Merchandise Building Tower on Chicago’s west side that served as the company’s headquarters until 1973. 

After Sears resigned in 1908, Rosenwald assumed control of the company and kept it going through the Depression. Rosenwald was the driving force behind opening physical stores. It was about this time that he brought in Robert E. Wood. Wood who created Allstate in 1931, later served as president and then as chairman after Rosenwald left. The first of their physical stores opened outside of Chicago in 1925 and over the years, others followed.³ The company designed the stores with motorists and modern shoppers in mind and outfitted them with air conditioning and individual departments.

The company continued to open stores, but had not left mail order behind: in 1933, they published their first Christmas Wish Book that sold just about everything including house kits. The company continued to do well and they established major national brands known today, such as Kenmore and Craftsman. The company had outgrown their headquarters and in 1974, they moved the headquarters into the newly built Sears Tower in downtown Chicago.

The 1980s and 1990s brew new challenges. In the 1980s, they expanded by buying Dean Witter and Coldwell Banker and introducing the Discover card, but these businesses weren't central to their traditional business and the company was forced to change course. By the end of the decade and into the 1990s, the company had sold the Sears Tower and most of the non-retail lines and ceased their long-running catalog. Then in 1999, the company was removed as a component of the Dow Jones Industrial Average where they had been since 1924. In 2004, Kmart Holdings Corp. bought Sears and the new company was called Sears Holdings Corporation. While the company did well for a few years, it was still heavily invested in bricks-and-mortar stores and was not exempt from the pressures brought on by online competition. The company sold off brands and continued to close stores. They filed for bankruptcy in 2018, but ultimately the hedge fund ESL Investments took ownership of the company through Transform Holdco.