Top image: "Southern Landscape," by Eldzier Cortor. Tempera and gesso on board, 1944 - 1945, Brooklyn Museum.
Rosenwald encouraged racist attitudes by building segregated schools.
Rosenwald used every means at his disposal to help African-Americans get an education and to support civil rights.
"Some people have criticized the School Building Program, along with many of Booker T. Washington’s ideas, for accommodating the segregated status quo. But in providing school buildings and an opportunity for education for children in places where little or none existed at all for many years, Rosenwald schools played a key role in educating generations of black children. In that sense, their legacy of opportunity is echoed in contemporary supplemental education initiatives like the Children’s Defense Fund’s Freedom Schools® Program, which provides summer and after-school enrichment for children in communities where the need for these kinds of quality programs is often greatest and public schools are failing to teach basic literacy and numeracy. Just as Rosenwald schools played a key role in serving as safe community havens and bringing adults together to nurture and support children’s education and positive development, CDF Freedom Schools programs seek to re-engage communities in the lives of their children. For the community members who worked together to fund and build Rosenwald schools, the black teachers who found employment in them, and the children they served, their promise and impact was unmistakable.” - Marion Wright Edelman, President Emerita and Founder of the Children's Defense Fund 
"There is documentation about the number of civil rights leaders who were educated at Historically Black Colleges (HBCs). Martin Luther King went to Morehouse, Andrew Young to Howard, or other African-Americans who supported Dr. King, most of whom were educated at HBCs. Many of those were founded near Rosenwald schools. St. Paul’s HBC, not far from my grandfather’s Rosenwald school, was a place where teachers of that Rosenwald School were educated because the founder of St. Paul’s college is also a founder of the Carol Boyd Rosenwald School. So in many cases the HBCs and Rosenwald Schools were revolving doors in that one fed the other. Alumni of Rosenwald Schools enrolled in HBCs, became school teachers, and returned back to Rosenwald Schools. The civil rights movement was really started by HBC alumni, and the connection between those students who either came out of Rosenwald Schools or were taught by alumni of the Rosenwald Schools is not a stretch. I firmly believe that connection is strong. And Rosenwald and the Fund also supported the HBCs – gave money to Morehouse, Howard, Fisk, etc." - Curtis Valentine, professor and education reformer whose grandfather attended a Rosenwald School 
"I think at the stage the country was at he funded the African-American community and gave them the tools to eventually end segregation. If you give people the ability to get an equal education, to feel self-determination, building your own schools, that will give you the tools to fight segregation. There was a debate happening between Booker T. Washington and W.E.B. Du Bois, and I think both were right, and in fact, Rosenwald gave to both of them...It’s fighting on all fronts." - Aviva Kempner, documentary filmmaker 
"You have to take what the reality of 1910s, 20s and 30s. You could not have built schools that were integrated at time in the South, they simply would have been bombed or destroyed. Opinion was such was that that couldn’t be done (and it was actually illegal or unconstitutional in many southern states.) The only way to make any kind of progress was to have schools that were segregated. It wasn’t necessarily something that he wanted but he was a businessman, he wanted to get some results, and this was the only way to do it....You have to remember, there were lynchings going on in the South then." - Peter Ascoli, grandson and biographer of Rosenwald 
"It may appear paradoxical that JR (Rosenwald) would support both Booker T. Washington and the...NAACP, which had W.E.B. Du Bois on its staff. The philosophical and political differences between the two men were well-known within the black community. Washington believed that Blacks should receive an industrial education that would fit them for work in a Jim Crow world and that Blacks should be accommodating to Whites. Du Bois believed that the black intelligentsia (the "Talented Tenth") should receive the same education as Whites and should oppose racial discrimination. JR was not the only white or Jewish philanthropist to support both Washington’s Tuskegee and Du Bois’s NAACP; Jacob Schiff did the same thing. In JR’s case, his support was based on the belief that Blacks deserved both legal rights and the right to a decent education." – Peter Ascoli 
Booker T. Washington limited African-Americans’ prospects by appeasing racists and focusing on industrial education.
There is some validity in this criticism.
"In all things purely social, we can be as separate as the fingers, yet as one hand in all things essential to mutual progress...The wisest among my race understand that the agitation of questions of social equality is the extremest folly, and that progress in the enjoyment of all the privileges that will come to us must be the result of severe and constant struggle rather than of artificial forcing.” - Booker T. Washington, speech at the Cotton States and International Exposition in 1895 in Atlanta, which came to be known as “The Atlanta Compromise” because it was seen as appeasing white racism.  (Read the entire speech)
"Mr. Washington distinctly asks that black people give up, at least for the present, three things — first, political power, second, insistence on civil rights, third, higher education of Negro youth — and concentrate all their energies on industrial education, the accumulation of wealth, and the conciliation of the South. This policy has been courageously and insistently advocated for over fifteen years, and has been triumphant for perhaps ten years. As a result of this tender of the palm-branch, what has been the return? In these years there have occurred: 1. The disfranchisement of the Negro. 2. The legal creation of a distinct status of civil inferiority for the Negro. 3. The steady withdrawal of aid from institutions for the higher training of the Negro. These movements are not, to be sure, direct results of Mr. Washington’s teachings; but his propaganda has, without a shadow of doubt, helped their speedier accomplishment." - W.E.B. Du Bois 
"Washington's argument that equality or black advancement would have happened naturally was wrong. In 1963, there were no black corporate directors. Eight years later there were over twenty. It is not a coincidence that these breakthroughs began happening during the civil rights era. They happened because of legislation, protests and boycotts. The very actions Booker T. Washington thought would hurt the cause of black people changed America." - Gregory S. Bell 
However, Washington's role in the founding of the Rosenwald School Program is indisputable, and his achievement in creating educational opportunities and institutions for African-Americans still stands.
"One of the main purposes of the Tuskegee Institute was to train teachers since there were not enough trained teachers available to teach African-American students. Washington urged the newly trained teachers 'to return to the plantation districts and show the people there how to put new energy and new ideas into farming as well as into the intellectual and moral and religious life of the people.'” - Causey 
"Washington gradually attracted notable scholars to Tuskegee, including the noted botanist and scientist George Washington Carver." - Causey 
"My general sense of Booker T. Washington is that he was committed to the betterment of black people in the United States and that he was very forward-looking and insightful. I think people often fail to appreciate his insights, particularly with regard to race relations. People need to view Washington as a pragmatist in the John Dewey sense of pragmatism, where you’re really working to solve a significant problem. Washington’s problem was: How do you resolve or improve race relations between black people and white people in the South, given the history of race and racism in the United States at that particular point in history? ...Washington never said, as many have claimed, that black people should only get an industrial education. He never said that black people shouldn’t participate in the political process...Washington's was not a consensus program. It was a program rooted in what he took to be the needs of the black southern masses at that moment in history." - Dr. Bill E. Lawson 
"Booker T. Washington didn't just build up a school; he built up a community."
"He was a man who was a slave and who didn't allow slavery to define him or who he was going to become. He built something that he saw in his mind's eye when no one else believed it was possible. He made other people believe in themselves and gave them opportunities to do things that they couldn't even imagine doing. At the end of the day, he went from slavery to dining with the president of the United States of America and helped to define a race of people during a time when that people was looked down upon as inferior savages. He was a great man." - Karen Hunter