What these presidents said in private and what they did in public were often sharply at odds.

Given America’s history of slavery, the stain that won’t go away, the argument could reasonably be made that all of our lily-white presidents, Obama excepted for obvious reasons, were racists. Out of our first 12 presidents, up to Zachary Taylor, all but John Adams and his son John Quincy Adams actually owned black human beings. Andrew Jackson, our seventh president and gracer of the $20 bill, may have been the most racist president of all. Despite significant opposition from Congress, Jackson forged the infamous Trail of Tears, forcibly relocating tens of thousands of Cherokee people to territories west of the Mississippi River. He sincerely believed that the removal would allow the Native Americans, “to cast off their savage habits and become an interesting, civilized, and Christian community.”

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Slavery-era presidents are the obvious candidates for the “racist” label. More surprising are these five 20th-century presidents who can compete for the title of most racist modern president.

1. Woodrow Wilson

Let’s start with a progressive Democrat, so our conservative critics don’t accuse us of right-wing bashing. Wilson is not on this list as a token, though. He earned the right to be called a racist. As president of Princeton University, he said, “The whole temper and tradition of the place [Princeton] are such that no Negro has ever applied for admission, and it seems unlikely that the question will ever assume practical form.”

As our 28th U.S. president, Wilson signed legislation making interracial marriage illegal in Washington DC, in order to, as he said, “reduce the social friction building up in American society.” The army under Wilson was segregated and most black people were not allowed to fight in World War I. When a delegation to the White House protested, Wilson retorted that, “segregation is not a humiliation but a benefit, and ought to be so regarded by you gentlemen.”

An apologist for Southern racism, President Wilson believed that the South was forced to enact racist Jim Crow laws as a consequence of harsh carpetbagger laws that were imposed during Reconstruction after the Civil War. The Ku Klux Klan, “began to attempt by intimidation what they were not allowed to attempt by the ballot or by any ordered course of public action.” Some historians have even accused Wilson of idealizing slavery, viewing slaves as “indolent” and masters as patient in dealing with them. Indeed, critics argue that Wilson held the opinion that slavery was wrong on economic, not moral, grounds.

2. Theodore Roosevelt

Next up, a progressive Republican. Teddy Roosevelt makes a surprise appearance on our racist list. Despite representing everything progressive Democrats see missing in today’s Republican Party, Teddy failed the test of tolerance. He was a devout follower of eugenics, the belief that there are superior and inferior strains of humankind, and that it is best to filter out the inferior brand in order to foster the development of mankind. “Society has no business to permit degenerates to reproduce their kind…. Some day, we will realize that the prime duty, the inescapable duty, of the good citizen of the right type, is to leave his or her blood behind him in the world; and that we have no business to permit the perpetuation of citizens of the wrong type,” he said.

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In 1914 Teddy Roosevelt said that, “criminals should be sterilized and feeble-minded persons forbidden to leave offspring behind them.” It was, of course, no mystery as to who the “citizens of the wrong type” were. Roosevelt once referred to Africans as, “ape-like naked savages, who…prey on creatures not much wilder or lower than themselves.” In a 1905 statement he asserted that Caucasians were “the forward race” destined to raise “the backward race[s]” through “industrial efficiency, political capacity and domestic morality.” Whites, he felt, needed to reproduce in abundance or else risk “race suicide.” Black people were not the only targets of his racism. He had this to say about American Indians: “I don’t go so far as to think that the only good Indians are dead Indians, but I believe nine out of 10 are, and I shouldn’t like to inquire too closely into the case of the 10th.”

3. Franklin Roosevelt

Not to be outdone by his wife’s famous Uncle Teddy, Franklin Delano Roosevelt, considered by many to be one of our greatest presidents, was a racist in his own spectacular way. Under his orders, more than 100,000 Japanese Americans were relocated and imprisoned during World War II for the crime of having Asian heritage.

Anyone who doubts this was racism need only compare this to way many hundreds of thousands of German Americans were treated during the war. In 1936, after the Berlin Olympics, FDR invited the athletes who competed for the U.S. to the White House. But Jesse Owens, who had won four gold medals, humiliating Adolph Hitler in the process, did not receive the invitation from the president. No surprise then, that Owens stumped for Roosevelt’s Republican rival, Alf Landon, in the 1936 presidential election. “Hitler didn’t snub me—it was our president who snubbed me,” Owens said during the campaign.

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Because he needed the political support of southern Democrats, FDR did not support anti-lynching laws. Roosevelt placed Jimmy Byrnes, a South Carolina overt racist in the Supreme Court, and almost named him vice-president instead of Truman in 1944, which would have made Byrnes president following FDR’s death. Apologists will argue, with some merit, that FDR’s New Deal programs should speak for him, and in truth, African Americans were widely supportive of him. Still, there is little doubt that FDR failed to transcend his time, and his views on race were not enlightened.

4. Richard Nixon

Nixon burnished his racist credentials in the 1968 campaign for the presidency by adopting the “Southern Strategy,” which entailed appealing to the racist nature prevalent at that time among white Southerners, insinuating that the Democrats sold out their interests to the African-American community via Lyndon Johnson’s Great Society programs. In adopting this strategy, Nixon turned a formerly Democratic South into the Republican stronghold that exists to this day, and secured the ultimate prize for himself, the presidency.

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Once in the oval office, Nixon, as we know, expanded what had been a more limited secret tape-recording system. Not only did this prove his undoing once Watergate reared its head, it also exposed Nixon’s private, vicious nature. He was recorded expressing opinions about all sorts of groups: Jews were communists out to legalize marijuana; the ancient Greeks and Romans were a bunch of “fags”; and African Americans were “Negro bastards” who preferred to live on welfare like “a bunch of dogs.”

Nixon, however, did see a future for the black community—though he belived it would take 500 years to accomplish: “They are coming along, and that after all they are going to strengthen our country in the end because they are strong physically and some of them are smart.” In another rant, he asserted that blacks couldn’t run Jamaica or any other country. “Blacks can’t run it. Nowhere, and they won’t be able to for a hundred years, and maybe not for a thousand … Do you know maybe one black country that’s well run?”

5. Lyndon Johnson

Anyone who has read anything about the life of Lyndon Baines Johnson knows what a complicated and contradictory man he was. On the one hand, modern black America can look at LBJ as a partner in the long and ongoing struggle for civil rights in the United States. It was LBJ who pushed through the civil rights bills in 1957, 1964 and 1965 that finally gave African Americans the same rights (at least on paper) as white America. On the other hand, there can be no question that Johnson was a racist who looked down on people of color as inferior. In the 1940s, he referred to Asians as “hordes of barbaric yellow dwarves.”

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During his congressional career, he was mostly a reliable part of the Southern bloc of politicians who thwarted civil rights bills at every turn. As president, when he appointed Thurgood Marshall to the Supreme Court over a lesser-known black judge, LBJ explained in private, “When I appoint a nigger to the bench, I want everybody to know he’s a nigger.” He even referred to his own Civil Rights bill as the “nigger bill.” Still, Johnson had enough self-awareness to say, about the struggle for civil rights, “It is not just Negroes but all of us, who must overcome the crippling legacy of bigotry.” There is little doubt he included (or should have) himself in that statement.