• He articulated the radical socialist critique of both Washington's accommodationist ideology and DuBois' legal struggle for civil rights (voting rights, anti-discrimination, equal education)
• He believed that the solution for the race's problem was to seek an alliance with the white working class and assert social rights (right to a job which pays a living wage, right to decent housing and medical care, right to an old age pension) through labor activism.
• As the editor of The Messenger, a New York City socialist publication, Randolph initially gained prominence due to his strident editorials opposing black soldiers fighting in WWI and criticizing President Wilson as a tool of the capitalist powers which had initiated the war.
• During the 1920's Randolph rallied the Pullman Sleeping Car Porters to form their own union to demand better pay and better working hours.
• After succeeding in organizing the first black union to be recognized nationally, he went on to criticize the major trade union organizations for excluding black workers.
• Randolph achieved national prominence by organizing a mass March On Washington in 1941 to pressure FDR into ending discrimination against blacks in federal jobs and in major corporations which do business for the government (particularly, the defense industry.) FDR gave in and ordered the desegregation of federal government jobs in Executive Order 8802. (but not the military)
• During the 1940's he helped to organize CORE, the civil rights group which pioneered peaceful civil disobedience: sit-ins and marches imitating Ghandi's successful campaigns in India.
• Randolph crowned his career by organizing the historic March on Washington for Jobs and Freedom in 1963.

• opposition to WWI, "a war caused by the machinations of capitalists and hence of little concern to workers.
• In The Messenger he called on blacks to resist the draft and focus instead on fighting for their rights at home..
• In The Messenger, he argued that the black worker had been lulled into a false sense of security by Booker Washington's accommodationist approach and the NAACP's gradualist approach to change. He called for bold socialist leadership: direct action to organize unions for black workers and organize rent strikes against inflated prices in the black belts of northern cities.
• He stridently criticized President Wilson during the war, referring to him as a capitalist stooge and a bigot. He was denounced in Congress as a "Bolshevik" and was investigated by J. Edgar Hoover for his connections to the Communist Party. (Hoover would soon become the head of the new FBI which was brought into being to fight organized crime and to contain the American Communist Party.)
• As an organizer of black workers, Randolph agitated among hotel workers, elevator operators, switchboard operators and waiters. He attempted to from inter-racial unions.
• He called on black voters to reject both major political parties, and in 1920 he ran for State Comptroller of New York on the Socialist ticket. However, in 1925 Randolph denounced the American Negro Labor Congress because it was run by Moscow.

• In August 1925 Randolph became the 'general organizer' for the Brotherhood of Sleeping Car Porters. He induced induce them to sign up for the union and then he planned to force the Pullman Company to recognize this union as the workers' legitimate representative in collective bargaining negotiations for a new contract.
• The porters sought higher wages (they lived mostly on tips). They also had to purchase their own uniforms and pay for their cleaning. They had to pay for all meals on the job, and they had to work 400 hours a month (compared to an average of 240 for typical railroad employees.)
• The Pullman Company opposed the formation of this union and used coercive methods to prevent it from coming into being: a company union, harassment and firing of anyone perceived to be a union organizer, threatening to fire all blacks and replace them with Asian immigrant workers.
• Black intellectuals and professionals were also cool to union organization (fearing to alienate wealthy philanthropists). These middle class leaders also looked down on black workers.
• Randolph's successful organization of the union depended on persistence, discipline and luck. He used The Messenger to criticize middle class black leaders who he claimed were 'bought and sold' by management. He gained the support of the NAACP and the endorsement of key black business associations. He also preached the gospel of work to the porters themselves. Their movement could only succeed if they modeled superb skills while on the job: "independence without insolence, courtesy without fawning, and service without servility."
• The fight to organize the union went on for twelve years until Randolph received a key assist from the federal government. In 1934 during the New Deal FDR and Congress passed the Railway Labor Act which outlawed company unions and granted employees the right to organize without company interference.
• In 1937 the Pullman Company capitulated and recognized the Porters' union, which negotiated a new contract for shorter hours and higher wages.
• With this victory Randolph could then press the large trade unions, like the AFL, to recognize them and drop the color line barring blacks from joining other trade unions.

• To end discrimination against black workers in federal government jobs, Randolph organized a march on Washington during 1941. Randolph also protested discrimination against blacks in armed forces and defense industries. America was preparing for war against Germany and Japan, and Randolph demanded that the country live up to its principles of liberty and justice not only in the fight against fascism but at home.
• FDR called a White House conference to meet with Randolph and the other march organizers, and after recognizing the strength of their preparation and resolve, FDR issued Executive Order 8802 which forbid discrimination by race, creed, color or national origin in government hiring practices. (FDR did not go so far as to end segregation against blacks in the US Armed forces.)
• To enforce this directive, Congress established the Committee on Fair Employment Practices (FEPC): the first time the federal government had assumed a key role in the elimination of Jim Crow practices. This move established an essential legal precedent: discrimination denies a civil right protected by the 14th Amendment.
• Typically, Randolph was not satisfied. He continued to pressure the government and threaten mass protests until 1948 when Harry Truman issued Executive Order 9981 which finally banned discrimination in the U.S. Armed Forces

He helped organize the Congress on Racial Equality (CORE) in 1942, the organization which developed the non-violent sit-in techniques that would prove so effective in breaking segregation in public facilities.