The bankruptcy filing this week by Sears likely marks the beginning of the end for the landmark retailer. And it’s equally likely that few remember the groundbreaking role that Sears & Roebuck played in breaking the power of the sugar oligarchy that dominated island business and politics.

On Thursday morning, May 8, 1941, Sears opened a modern new store on a large piece of land bounded by Beretania and Young Streets, and the upper block of Kalakaua Avenue. The site had been consolidated from 15 separate parcels that Sears bought for a reported $100,000. The new Honolulu store was said to be the most modern of the department store chain’s 595 stores across the U.S.

The store boasted “a tree shaded, paved parking area accommodating easily 300 autos.” Apparently large parking lots were unusual and noteworthy at that time. The store contained 47,000 feet of retail space and an additional 50,000 feet of warehouse space.

It was news, with several full pages of the Honolulu Star-Bulletin devoted to singing the praises of the new store.

But left out of the all the glowing reporting was the fact that Sears entry into Hawaii came over the opposition of Hawaii’s Big Five and the oligarchy that controlled the islands’ plantation economy.

The Big Five was made up of the five major sugar factors: Alexander & Baldwin, Amfac, C. Brewer, Castle & Cooke, and Theo H. Davies.

Here’s an extended excerpt from a chapter in economist Thomas Hitch’s 1992 book, “Islands in Transition: The Past, Present, and Future of Hawaii’s Economy.”

Toward the end of the plantation era shortly before World War II, the Big Five collectively were the power center of Hawaii–the center of economic power, political power, and social power all rolled into one. Economically, they represented most of the sugar industry, and three of them controlled most of the pineapple industry as well, Four of them controlled Matson Navigation Company, which was not only the main common carrier operating between the mainland and Hawaii but also the owner-operator of Hawaii’s two largest hotels–at a time when the territory had only a dozen tourist-class hotels. Most of the Big Five were also involved in merchandising, supplying stores and shops throughout Hawaii. One of the Big Five owned the main foundry and machine shop(the Honolulu Iron Works), and others were engaged in stevedoring, railroading, water supply, and representing other steamship lines other than Matson.

In addition to running their own firms, Big Five officers held commanding posts in most of the other large businesses in Hawaii. A network of interlocking directorships made the whole business community, when the chips were down, all members of one family. This network as of 1939 was charted by James Shoemaker. Board members of the Big Five were shown in the center of the chart, and the directors of severity five other major Hawaiian companies were printed around its periphery. Wherever a Big Five director also appeared as a board member of one or more of the seventy companies, lines connected the names. The result was a chart resembling an immense, tightly-woven spider web. While this interlocking resulted partly from teh small size and isolated location of the Hawaiian community, the inevitable result was an emphasis on cooperation rather than on competition and a solid front by almost the entire business community in the face of any threat to its security or supremacy. Most such interlocks were abolished by Hawaii’s anti-trust law of 1961.

Virtually the only major companies in prewar Hawaii outside of the Big Five network were the national companies whose branches in the territory constituted the local pineapple industry–California Packing Corporation (now Del Monte); Libby, McNeil & Libby; and the American Can Company, which supplied them. These firms all operated in Hawaii for decades, long enough to do business alongside–though only marginally in competition with–the Big Five. The opening of a large Sears Roebuck retail store in Honolulu in 1941, over the opposition, it was said, of the Big Five, broke the pattern and presaged the new order that was to come after Hawaii became a state. (emphasis added)

Hitch had a long career, serving 23 years as the widely quoted chief economist at First Hawaiian Bank.

When Sears was first assessing the potential for establishing a Hawaii store, Matson apparently let it be known that its ships would not transport Sears merchandise to the islands. After all, Sears would become a direct competitor to Liberty House, part of the Big Five’s network of retail businesses. Matson reportedly relented only after Sears threatened to support a new shipping line offering service between Hawaii and the U.S. mainland.

The Big Five oligarchy maintained power for three more decades, but Sears was the first to successfully pose a direct challenge its attempt to monopolize the islands’ economy. More followed. Sears was the first.