Brian Kilmeade Reveals How Teddy Roosevelt and Booker T Washington Changed America's Racial Future

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Brian Kilmeade Reveals How Teddy Roosevelt and Booker T Washington Changed America's Racial Future

Brian Kilmeade joins Will Cain to discuss his latest book on two unlikely allies who shaped America's path toward racial equality. The Fox & Friends co-host explores why Booker T. Washington's vision of self-empowerment has been overshadowed in modern civil rights narratives, and how Theodore Roosevelt's controversial dinner invitation sparked a national firestorm. Kilmeade unpacks the complicated legacy of both men, Roosevelt's Progressive politics and masculine ideals, and Washington's focus on education and economic independence over grievance. Their friendship reveals a nuanced chapter of American history that challenges modern assumptions about race, progress, and what it means to judge historical figures by the standards of their time.

November 27, 2023

The Forgotten Vision of Booker T. Washington

Brian Kilmeade discovered Booker T. Washington's story while researching his previous book on Frederick Douglass and Abraham Lincoln. Reading "Up From Slavery," Kilmeade was captivated by Washington's firsthand account of being called to the main house on a plantation and told he was free. Washington never had shoes as a child, never remembered sleeping anywhere but the dirt floor, ate the same meal every day, yet rose to become one of the most influential people in America during the 1860s and 1870s.

As Kilmeade researched Washington's life, Theodore Roosevelt kept appearing throughout the story. To verify this wasn't a forced connection, Kilmeade consulted Tweed Roosevelt, Teddy's great-grandson who runs the Roosevelt School at LIU, the same institution Kilmeade graduated from. Tweed confirmed the connection was authentic, though he warned that Teddy had some blind spots that showed he was a man of his times. Nevertheless, Roosevelt was genuinely inspired by Washington as a self-made man who defied all odds.

Kilmeade argues that Booker T. Washington has become somewhat of a forgotten man in the advancement of African-American civil rights. While schools and buildings bear his name everywhere, Washington's vision for black advancement appears to have lost out to W.E.B. Du Bois and the idea of direct conflict over civil rights. Du Bois advocated for direct action and a progressive dynamic of group advancement, whereas Washington championed individual bootstraps advancement and self-empowerment.

However, Kilmeade believes historical figures experience ups and downs in how they're perceived. He points to Ulysses S. Grant as an example—once dismissed as corrupt and an alcoholic, Grant's reputation has been rehabilitated by deeper examination of his life and accomplishments. The people around Grant were corrupt, but he wasn't. He did drink, knew he had a problem, and it occurred in surges that hurt his military career but didn't damage his presidency.

Similarly, Booker T. Washington may not be the hottest name in some quarters of the black community today, but figures like Colonel Allen West and Thomas Sowell interpret his legacy very differently. They appreciate what Washington wanted out of life and where he believed America could go.

Washington's Philosophy of Action Over Grievance

From Kilmeade's perspective, what sets Booker T. Washington apart is that he didn't know the word grievance. He didn't sit and complain—he was a man of action. When someone didn't like him, Washington didn't waste energy on hatred or resentment. He simply moved on to people he could work with.

This mindset gave Washington the courage, strategy, and focus to knock on doors in Massachusetts and New York, introducing himself and explaining his small school in Tuskegee. He sought support to grow the African-American community, teach skills, and provide great education. When doors slammed in his face, he didn't harbor resentment—he just moved on to the next opportunity.

Kilmeade finds this approach profoundly relevant today. When people dislike you, the worst thing you can give them is your hatred because that means giving them your focus. Reading about Washington's focus in the 1880s and 1890s, Kilmeade realized there was much to learn from someone who didn't let others' negativity land on him.

While W.E.B. Du Bois argued it was wrong that people were treated differently, wrong that blacks couldn't get into certain schools, wrong about segregation and prohibitions on interracial marriage, Washington acknowledged these injustices but took a different approach. He recognized the reality he lived in and the region where he operated. He concluded that activism would accomplish little, so he chose to be an educator instead.

Kilmeade loves this focus and believes that even if people don't appreciate Washington's approach in 2023, they might value it in 2027 or 2037. There's a long arc to history, and it doesn't move in a straight line—it has ups and downs.

The Tuskegee Model: Education Through Practical Skills

Booker T. Washington was one of the last great activists born into slavery. His vision centered on creating colleges like what became the Tuskegee Institute, where students would learn technical skills and hands-on application of education. His goal was to build up the black community's capacity by accumulating education and wealth.

Parents of newly freed slaves would come wanting their children educated. Washington promised education, but when he explained the children would also learn skills and work in the fields, some parents objected—they didn't want their children in fields. Washington clarified that students would build the school itself. In a style reminiscent of "The Karate Kid," students got the fence painted while learning defense—they constructed the school while learning valuable skills and trades.

Students attended classroom sessions in night school and day school, divided by schedule, and each chose a trade: carpentry, agriculture, brick-making, brick-laying. Women had jobs as teachers, seamstresses, or in farming and food production. Everyone developed a skill.

Washington's reasoning was practical: upon graduation, there would be reluctance among white employers to hire black workers. Therefore, students needed to make themselves indispensable. Washington didn't hate America as it existed—he recognized reality and was willing to compete within it.

Washington essentially told his students that there was no doubt it would be harder for a Negro young man or woman to succeed in America. But by clearing obstacles and overcoming difficulties, they would be far more prepared for the success they would eventually achieve. The hardships they faced in getting there would make them stronger as parents, in their careers, and as role models.

Kilmeade often got chills reading Washington's words. Washington acknowledged the difficulty ahead but assured people they would get there, and when they arrived, they would be thoroughly prepared. As a parent reviewing these ideas, Kilmeade sometimes felt bad for someone born on third base because Washington's philosophy suggested that those who overcome greater obstacles develop greater strength.

Washington wrote about seventeen books. Teddy Roosevelt endorsed and wrote the forward to what Kilmeade believes was Washington's last book. Roosevelt loved reading it, and along with his wife, they received a pre-release copy. In April 1901, Edith Roosevelt told Teddy, who was vice president at the time, that he needed to meet Washington—this was his ticket to understanding the South. They met and pledged to work together.

Theodore Roosevelt: The Complicated Progressive

Theodore Roosevelt presents a complicated figure for modern conservatives. On one hand, there's much to admire: his overt embrace of masculinity, his love of the West, his desire to be a cowboy and cattle rancher in the Dakotas, and his philosophy of living a strenuous life. He took up jujitsu at various points and believed in constant physical and mental challenge.

On the other hand, Roosevelt was either the father or an early adopter of the Progressive Movement. He left the Republican Party to found the Bull Moose Party, also known as the Progressive Party, and ran for president under that banner. He advocated trust-busting and an eight-hour workday during the rough-and-tumble times of the Industrial Revolution.

Kilmeade acknowledges people can look back at what Roosevelt stood for and decide for themselves, but emphasizes that Roosevelt was willing to take on the establishment in every way. As police commissioner, he went out with a journalist and photographer to document illegal immigrants making cigars in small, dilapidated, unregistered apartments where they were being exploited. He was willing to get his hands dirty and go into rough areas of the city.

Roosevelt took on law enforcement reform, setting up an academy, establishing rules, providing uniforms, setting hours, and creating structure. He also accepted a job to break up bureaucracy under either Hayes or Grover Cleveland. A Republican hired him, but Cleveland kept him because he was efficient at breaking up bureaucracy, establishing accountability and timeframes for accomplishment, and creating his own meritocracy.

Roosevelt was an environmentalist in the sense of setting up state parks across the country and preserving territories. But he was also a pull-yourself-up-by-your-bootstraps individual who emphasized accountability, integrity, and honesty. He asserted himself in various places to make the country better. While he had a healthy ego, he also had a remarkable intellect—he was a speed reader with an apparently photographic memory who read a book a day.

Roosevelt's views were somewhat diverse compared to how Republicans are viewed now, but the party itself has changed. Ten years ago, Republicans had a different perception than they do now. Since Trump, the party has become more of a blue-collar, working-man party.

According to Tweed Roosevelt, there was going to be another chapter in Teddy's political career. After he lost and divided the Republican Party—taking more votes than Taft and giving the election to Woodrow Wilson—the Republicans agreed to let him back in. They were queuing up Teddy to run in the next election, but he died at 59 or 60 years old.

Roosevelt's Blind Spots and Growth on Race

Judging Roosevelt requires understanding him as a man of his times. He thought whites were superior to blacks in some ways, yet simultaneously pushed for equality. He appointed people to judge positions and postmaster positions, including Minnie Cox and William Crum, and pushed back against anyone who said they couldn't do the same job as a white man.

Roosevelt told Booker T. Washington he would use him as an advisor and asked Washington not to tell him someone's color or gender—he just wanted the best person for the job. At the same time, when speaking to Southern audiences, Roosevelt sometimes said things he believed they needed to hear to win their votes.

Despite these contradictions, Roosevelt's actions spoke volumes. He served on Tuskegee's board, did great work there, and delivered an incredible commencement address that had to overcome his own preconceptions. Kilmeade notes that Lincoln said things suggesting everyone deserves to be free but that not all were equal. Lincoln later evolved, though he never explicitly said he had changed—you just see it in reading his later speeches.

Benjamin Franklin owned slaves but died as an abolitionist. Early in life, he believed whites were smarter than blacks, but when he saw African-Americans getting educated, he admitted he was wrong. If the smartest and most versatile man to ever live could admit he needed to grow, then Roosevelt's evolution becomes more understandable.

Roosevelt couldn't help who he was born to or the environment he grew up in. His mother was with him constantly while his father worked. She likely said many things about growing up with slaves. The Civil War wasn't something Roosevelt had to read about—he was six years old when Lincoln was assassinated. He could simply talk to his mother and family to hear about it firsthand.

If Roosevelt said racially insensitive things, Kilmeade understands why, given that context. But as Roosevelt evolved and grew, he demonstrated real progress. He spoke at Booker T. Washington's funeral and said Washington was a credit to his race—the human race. And Booker T. Washington never said anything but great things about Roosevelt.

The Dinner That Shocked America

The most consequential moment in the Roosevelt-Washington relationship was the dinner invitation to the White House in the early 1900s. Neither man realized it would become such a big deal. Washington had more sense it might be problematic, but Roosevelt seemed genuinely oblivious.

When Roosevelt was governor of New York, blacks slept over at the governor's mansion all the time. He didn't think it was a big deal. He had served with the Buffalo Soldiers, a black unit in Cuba, and didn't think that was a big deal either. When he heard Booker T. Washington was in Washington D.C., he wrote him a letter—which still exists and is included in Kilmeade's book—asking Washington to come over for dinner.

Washington worried about any negativity that could affect Tuskegee and felt he shouldn't accept, but wondered how he could turn down the president. If not for one person asking to see the guest book, discovering Washington's name, and realizing a black man had dined with the President of the United States and his family, it might have passed without notice.

The revelation created a huge firestorm because it had never been done before. Kilmeade admits that in researching this, he often had to remind himself why it was such a problem—the answer wasn't instinctual to a modern researcher. For people at that time, particularly in the South, this was a bad message. Segregationists wanted to ensure blacks did not become equal with whites and were willing to segregate schools, businesses, and prohibit interracial marriage to maintain that separation.

When the most famous black man in America had dinner with the most powerful man in America, segregationists feared this could create a ripple effect leading to actual equality. The horrible headlines that resulted—which Kilmeade includes in both his book and Fox Nation special—made both men decide to continue their relationship but be more discreet about it.

The ongoing relationship meant no more dinners at the White House, but they continued to meet and consult. Some criticized them for giving in to the pressure, but Kilmeade sees it differently. Two weeks or possibly two months later, both men were invited to speak at Yale, where Washington would become the first to receive an honorary degree from that institution. They stayed away from each other at the event.

Mark Twain, who never liked Teddy Roosevelt and thought he was a showman and show horse, loved Booker T. Washington. At the Yale event, Roosevelt approached Twain and asked if he thought Roosevelt had made a mistake. Twain responded that the way Roosevelt did it and the timing could have been better thought out, but he wasn't necessarily wrong. Twain seemed to think Roosevelt made things harder for Washington, not necessarily for himself, and should have thought it through more carefully. However, nothing Kilmeade read suggested either man anticipated the firestorm at all.

Kilmeade includes in his special a clip of John McCain's concession speech after losing to Barack Obama. McCain said there was a time when Booker T. Washington being invited to the White House was controversial—a black man eating with a white family. Now a black man would be hosting that dinner. That's how far America has come.

The Relationship's Impact and Limits

What was the impact of Booker T. Washington on Teddy Roosevelt? Kilmeade believes Roosevelt simply saw what a black man was capable of if given the opportunity to learn. To understand what Roosevelt thought, Kilmeade suggests reading his commencement address at Tuskegee. The beginning appears to be ad-libbed because Roosevelt looked out after taking a tour and saw these men and women—teachers and students—so industrious, innovative, and productive. They learned basics of hygiene, how to present themselves, how to make eye contact, and academics. Roosevelt seemed overwhelmed by what this man had accomplished.

Both men understood their relationship wasn't about them—it was about their causes. Roosevelt wanted to make America better, and Washington wanted to make the experience of black men and women better in America. That was more important than their personal relationship, and they demonstrated this on a couple of occasions.

When the Buffalo Soldiers got involved in a controversy, Booker T. Washington told the president he was wrong, that it wasn't the soldiers' fault, that the charges were trumped up, and that Roosevelt should not punish the whole unit. Roosevelt disagreed—he said they were involved, and they were all court-martialed.

Another instance occurred when Roosevelt, running against Taft and Woodrow Wilson, asked Washington for an endorsement. Washington asked himself what was better for his cause. If he endorsed Roosevelt and Roosevelt lost, it would hurt Tuskegee. He told Roosevelt he couldn't endorse him and hoped he would understand. Roosevelt said he did understand, because it was all about the cause, not about them.

Kilmeade acknowledges Roosevelt needed a big ego to accomplish what he did, but also believes the man bled red, white, and blue.

Lessons for Modern America

The impact of Booker T. Washington on Teddy Roosevelt demonstrates the power of a single individual—seeing a man as a man and recognizing what one can accomplish regardless of affiliation, group, or race. It shows the unlimited potential of the individual.

Regarding where America is now, Kilmeade hopes that black and white relationships are at a high point. Outside of perhaps the historical blip of the last five years, he believes that on an individual basis, this is the case. Looking at human behavior, Americans are more integrated—not completely, but more than ever before. They are intermarried and work together as co-workers at levels never before achieved in American history.

Yet there's also this activist moment of embracing racial essentialism. What can be learned from Teddy Roosevelt and Booker T. Washington for modern America?

Kilmeade suggests that everyone has certain preconditions in life—the parents they have, the schools they attended, the town they grew up in. Most people had nothing to do with these circumstances. They didn't make decisions at six, seven, or eight years old about where to live, unless they were from a military family or their parents moved.

If Roosevelt and Washington could overcome the circumstances of their birth—slavery for Washington and Roosevelt's severe health problems that almost killed him from asthma—then everyone has something they can overcome. You can make life a university, or you can resign yourself to your circumstances. All great people evolve, and people shouldn't be hard on themselves if they felt one way in 2004 and differently in 2010.

Kilmeade points to examples like Ken Griffey Jr., who stood up during a celebration of a great Seattle Mariners team and pointed out Jay Buhner was a white guy. Griffey said that despite their completely different backgrounds, they had become so close that if anything happened to Griffey and his wife, he had made it clear Jay Buhner would raise his children. Why isn't that example rippling throughout the country?

Sports led the way with integration in baseball and football, making people think differently in the stands and the locker room. How many times do you see moments like Aaron Rodgers talking to Davante Adams with the Raiders, hugging each other and talking about what they mean to each other? Why isn't that held up as an example? Do they care about black or white? They don't even think about it.

But America seems to go out of its way to make people think about race. Kilmeade believes we should be aware we're being manipulated and not let it happen. Be racially sensitive—Tim Scott once said President Trump is not racist, sometimes just racially insensitive. Being told something wasn't the best thing to say doesn't mean someone is racist.

Everyone walks around on eggshells, not wanting to offend. Kilmeade thinks we have to start realizing there's nothing separating us. Most people don't look at anybody differently. If you can help my team, my company, my neighborhood, they'd love to have you. They don't care what color you are, what gender you are, whether you're gay or straight—they care what kind of person you are. Most people agree with that, and Kilmeade believes some go out of their way to make it seem like we don't.

The moment between Ken Griffey Jr. and Jay Buhner should be a model for all of us as individuals. Teddy Roosevelt and Booker T. Washington provide a great model of an individual relationship that helped move the country forward.

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