The brain child of brothers Harold Toppel and George Toppel, Pueblo began as a single store operation, in the Roosevelt Avenue in Puerto Nuevo, San Juan, Puerto Rico. The wide success of the first store meant that soon the Toppels would open 43 other Pueblo Supermarkets around the island, and by 1960, they became a public corporation that began trading on the New York Stock Exchange.
1963 saw Pueblo expand out of Puerto Rico's boundaries and into St. Thomas and St. Croix, becoming a popular supermarket chain with the beautiful people of those two islands. The fact that Puerto Ricans often fly to these destinations for weekend trips, also made these 2 islands a good choice for Pueblo to operate at, because Pueblo made the Puerto Rican tourist feel at home in the Virgin Islands.
Pueblo introduced the trademark Pueblo Foods, which produces anything from paper towels to rice, and is sold on all of Pueblo's stores. It isn't uncommon to see someone come out of a Pueblo supermarket with a few cans of Pueblo tomato sauce or Pueblo olives in their shopping carts. In addition , Pueblo sells the top brands, like Coca-Cola, Pepsi, Arroz Sello Rojo, Bacardi, Charmin, Ball Park Franks, Eveready, Dannon, Casera sauce, Frito-Lay and many others.
In 1983, Pueblo inaugurated the Pueblo Xtra concept, a concept where the client could go and shop for food in a larger and more spacious space. In 1990, Pueblo brought over the Blockbuster Video company to Puerto Rico and the Virgin Islands.
In 2003, Pueblo faced financial troubles, but there were rumors of a potential buyer coming from Venezuela. However, Pueblo's management remained optimistic about the company's future.