It is the main route connecting the neighborhoods of the Vila Mariana subprefecture to the central region of the city and belongs to the North-South Corridor.

[1][2][3] In 1927, former Mayor José Pires do Rio commissioned a road system from a group of urban planners, who suggested the "valley floor theory", which involved the creation of a network of avenues and radial and perimeter roads that would orient and structure the urban growth of the city of São Paulo using valley floor and lowland areas, composed of wetlands and areas of low real estate value.

The original project only envisaged a connection between the city center and Ibirapuera Park; in 1958, it was included in the Urban Diametral Expressway Plan under the name 23 de Maio Avenue, established by Ordinary Law number 4,473 of May 22, 1954.

[5][13][14] The São Paulo City Hall faced many difficulties with expropriations, as most of the land to be removed consisted of valley bottoms and backyard areas, restricted by law.

[15] In 1962, a new decree expropriated an area of around 8,000 to 9,000 square meters covering the block between Cubatão, Estela, Oscar Porto and Tomás Carvalhal streets, where the tunnel that would pass under Largo Guanabara would terminate.

[5][17] Another problem were the structures that already stood on or next to the route, such as the garages of the Municipal Funeral Service, which occupied the lower part of the Dona Paulina Viaduct, and the large foundations of the planned headquarters of the Department of Highways, located next to the Mauá Palace.

In 1961, former Mayor Prestes Maia announced the resumption of work on the avenue, but was criticized by people who thought the Radial Leste was more important.

On September 9, 1964, the public notice for the construction of the Condessa de São Joaquim Viaduct was published, with expected investment of R$250 million.

In the 1970s, due to poorly designed curves and bad sidewalk, the avenue was considered dangerous and around ten people died every month on average during that time.

[35] On the first day, 708 fines were levied on the North-South Corridor, most of them in the stretch comprising avenues Vinte e Três de Maio, Moreira Guimarães, Rubem Berta and Washington Luís.

[38] Época magazine considered that the implementation of bus lanes in the city was one of the reasons for Mayor Fernando Haddad's fall in popularity, due to the perception of increased traffic.