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On November 4, 2008, Sean Jackson hesitated in the voting booth in West Palm Beach, Florida. He disagreed with Barack Obama on every issue and had vowed never to vote for someone just because of their skin color. Jackson is Black and wanted to be able to tell his grandchildren that he had voted for the first Black president, but he is also a loyal Republican. For his first presidential election he couldn’t quite fathom voting for a Democrat, especially since, as a Floridian, his vote was pivotal. “It took me 30 minutes to do it,” Jackson tells me. Would he also tell his grandchildren that he instantly regretted it? “Honestly, I did it against my own conscience,” Jackson explains. “He told us on the campaign trail that he was going to fundamentally change the course of this nation, and, dammit, he did just that.” 

For the next 12 years, Republican politics began to organize Jackson’s life. Not wanting to make the same mistake twice, Jackson voted for Mitt Romney in 2012, despite seeing him as “nothing more than just an egotistical SOB who just wanted to be president.” In 2015 Jackson became the leader of the Black Republican Caucus of Florida—a loose organization that is not part of the official Republican Party of Florida but one that Jackson has used to steer Black support to candidates. He threw his weight behind Gov. Ron DeSantis in his bids for US Senate and then governor. Soon it was time for another presidential election, and Jeb! Bush was his man. As for a Trump candidacy? “There’s no way in hell, uh-uh, ain’t happening,” he recalls thinking. “He can forget about it.” But after Jeb dropped out, when there was no other choice against Hillary Clinton, Jackson went “balls to the wall” for Trump.

“He started to grow on me,” Jackson admits. “I started to like him and became very enthused.” His character and behavior aside, Trump championed views cherished by people who call themselves Republicans: personal responsibility, organized religion, opposition to abortion, big tax cuts, and small government. At the same time, his overt racism and bizarre insistence that he has been the best president for Black people since Abraham Lincoln have caused many people who consider themselves to be Black Republicans to have second thoughts at the ballot box.

Jackson’s affection for Trump certainly did not sit well with his family. They criticize him for his Republicanism, which he dismisses because “they don’t know no better” and “don’t want to hear reason.” 

Because politicians and the media see Black people as a political monolith, they tend to treat Black supporters of Trump as a spectacle—the zanier they are, the more attention they’re given. Even during more ordinary times, Black Republicans are often approached like a sideshow within their own party, put on display by their white, uh, confederates as a demonstration of the GOP’s broadmindedness. See! We’re not racist! The combination of zany and we’re not racist explains how Diamond and Silk grabbed the spotlight on the national stage. It explains the ongoing presence of Candace Owens, a popular right-wing controversialist who heads Blexit, an organization that focuses on persuading Black people to leave the Democratic Party and join the Republican cause.

The elevation of the kooky Black Republican obscures the presence of people like Jackson and the Black conservative tradition they draw on (and in some ways reject). I’m neither a conservative nor a Black conservative—crucially, these identities are not synonymous—and I’m certainly not a Republican. But I am Black, and I’ve grown increasingly frustrated with the racist myth that Black people are an unvariegated mass of automatic liberals, as if our political ideologies weren’t as complex and crosshatched as anyone else’s. All sorts of white people are said all the time to “vote against their own interests,” and while we might reject such a programmatic conception of “interests,” there’s no denying that these Americans are treated as a serious voting bloc deserving of nuance and empathic magazine prose. When Black people do it, they are made to look like clowns.

I want to understand people like Jackson and, for that matter, Diamond and Silk. What drives a Black person in the time of Trump to be a member of a political party that can barely contain its contempt for Black Americans? Has Black Republicanism become completely untied from Black conservatism?

“The major difference between Black conservatives and Black Republicans is the belief in systemic racial oppression,” says Tasha Philpot, a professor at the University of Texas and author of Conservative But Not Republican: The Paradox of Party Identification and Ideology among African Americans. “It’s the notion of linked fate, the idea that African Americans see their fates intertwined with other African Americans.” Black Republicans “don’t put their race above all else,” Philpot says. “They believe that racism is more of an individual experience.” With a president who doesn’t bother to dress up his racism in the usual genteel finery, many Black conservatives have fled the Republican Party, and yet there remain Republican faithfuls like Jackson who choose to accept the bigotry for the sake of—well, for the sake of what?

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Let’s start with a look at polling data, a snapshot of preferences that are distinct from strict party affiliation. Despite being the Democrats’ most reliable voting bloc, Black people skew conservative on some major cultural issues. A 2019 Pew Research poll found only 51 percent of Black people supported gay marriage, compared with 62 percent of white people. In a 2020 Gallup poll, 46 percent of Black respondents said abortion was morally acceptable. But other polling shows that a majority of Black people do support a legal right to an abortion. And while a majority of Black people support gun control laws, after Dylann Roof, a white supremacist, murdered nine Black worshippers in a historic church in Charleston, South Carolina, some Black people began to wonder if guns could help protect themselves and their families from racist violence. Since the George Floyd protests began, more Black Americans are considering arming themselves. Philip Smith, the president of the National African American Gun Association, told Politico that his organization has grown by as many as 2,000 new members every day, a number he used to see only annually. Concerns about “law and order” have remained another touchstone for Black conservatives. As Michael Steele, the former chair of the Republican National Committee, told me, “We don’t need another white man threatening us with law and order. We support law and order. We get law and order. What we’re after is equality.”

But you need some history to explain how we arrived at a place where the conservative views of Black people don’t necessarily manifest in Republican votes. The story of Jackie Robinson, the first Black man to break Major League Baseball’s color line when he played for the Brooklyn Dodgers in 1947, is instructive. Robinson was a loyal Republican. This was not terribly bizarre in the 1950s. While Black people had begun migrating into the Democratic column in the 1920s, the party’s appeasement of its racist Southern wing meant that a significant share of Black votes was up for grabs in the 1950s. Republican President Eisenhower, who sent troops into Little Rock to enforce a school desegregation order and oversaw the passage of the first civil rights bill since Reconstruction, won an estimated 39 percent of nonwhite votes in 1956.

Still, Robinson’s friends were stunned when he supported Richard Nixon, Eisenhower’s vice president, against John F. Kennedy in 1960. Robinson saw Kennedy’s outreach to Southern governors as implicitly supportive of racism and naively considered Nixon someone who would not pander to that constituency. A revealing exchange between Robinson and the RNC’s campaign director took place after Nixon’s defeat. “I was terribly disappointed over the election and feel we are at a great loss,” Robinson wrote him. “I cannot help but feel we must work for a two-party system as far as the Negro is concerned.” The campaign director thanked Robinson and replied, “Personally, it is my judgment that you could be a ‘Messiah’ for the Republican Party in the days ahead.”

Robinson never got a chance to be the GOP’s Negro Messiah. The civil rights revolution was realigning American politics, forcing Democrats to shore up their losses by enfranchising more Black voters and imposing reforms on the South. In 1964, Barry Goldwater became the Republican presidential candidate. Jackie Robinson attended the GOP convention that year and warned that Goldwater’s nomination—and the abuse that was heaped on Black delegates—indicated the party was no longer “the party of Lincoln.” Instead, Robinson wrote a New York Herald Tribune op-ed in which he decried “a new breed which is seeking to sell to Americans a doctrine which is as old as mankind, the doctrine of racial division, the doctrine of racial prejudice, the doctrine of white supremacy.”

Robinson was describing what would become known as the Southern strategy, whereby the GOP courted white Southerners by appealing to racism. Today we can say with more certainty that the racial radicalization of the Republican Party was a national phenomenon, not regional, and that the influence was running in the other direction—it was white suburbanites turning the Republican Party into a means of upholding the racial order. After 1972, Republicans presidential candidates would only average 10 percent of Black support.

In response to the advances made during Lyndon Johnson’s Great Society initiative, the Nixon administration concocted policies that would dismantle the programs established by Johnson to fight poverty. Behind the scenes, the racism was much more explicit. One 1971 conversation between President Nixon and California Gov. Ronald Reagan was recently revealed by Tim Naftali, a professor of history at New York University. Reagan disparaged the African delegates to the UN as “monkeys from those African counties—damn them, they’re still uncomfortable wearing shoes.” Nixon responded with a laugh at the gross characterization. A year later, Nixon, who championed “the great silent majority” (yet another in a long list of euphemisms for white people), sought to put a moratorium on school busing that was intended to bring some measure of equality to American education.

The ensuing decades brought high-profile Black conservatives like Clarence Thomas into greater prominence. Thomas used his nomination to Thurgood Marshall’s seat on the Supreme Court as proof that racism was over. (Never mind that he called his hearings, which involved sexual harassment allegations against him, a high-tech lynching.) A cadre of Black conservative intellectuals were heralded in a 1981 story in the New York Times Magazine. The lead gave credence to Black people who were simply tired of racism: “Nathan Wright Jr., educator, author and chairman of the National Assault on Illiteracy Program, is convinced that racism no longer has a ‘damn thing’ to do with the still-perilous predicament of black America and that Ronald Reagan, a man of ‘principle and pragmatism,’ is committed to helping blacks advance.”

One of the people featured in this story was Thomas Sowell, an economist whose personal story involves bootstrapping his way out of poverty to a PhD in economics from the University of Chicago. That narrative became, for him at least, the model that all Black people could replicate. Sowell never felt impeded by Blackness. Those who did, obviously, were lazy.

In the 1981 Times article, Sowell insisted that the combination of “the political interventionist state” and self-interested Black civil rights leadership have damaged Black people, a theme he would repeatedly revisit for decades to come. In a 2015 essay for the conservative publication National Review, revealingly titled “The Inconvenient Truth About Ghetto Communities’ Social Breakdown,” Sowell wrote, “You cannot take any people, of any color, and exempt them from the requirements of civilization—including work, behavioral standards, personal responsibility, and all the other basic things that the clever intelligentsia disdain—without ruinous consequences to them and to society at large.”

With the election of the first Black US president in 2008, the GOP went apocalyptic. The tea party movement, at its core a backlash—a whitelash, if you will—to his presidency, was overt racism masquerading as a call for lower taxes and less government intrusion.

Enter Michael Steele as the new head of the GOP. Under Steele’s leadership, the Republican Party attempted to move away from the Southern strategy. Although Steele left his post in 2011, the GOP’s soul-searching intensified with the 2012 defeat of Mitt Romney. The party conducted a much publicized “autopsy report” that asserted that the party had to diversify to stay relevant. “We need to campaign among Hispanic, black, Asian, and gay Americans and demonstrate we care about them, too,” the report read. Not that it made much of a difference. Four years later, the party’s new standard bearer doubled down on the fear, racism, and xenophobia.

Decades of encouraging and embracing bigotry culminated in a second whitelash with the election of Donald Trump, whose expressions of overt racism began long before he descended the golden staircase and announced his candidacy. A few weeks before the 2016 election, Steele announced that he would not be voting for Trump. “I believe in this idea of individual rights and liberties,” he told me. “While the leaders may have been flawed, those principled ideas transcend those flaws.”

We all know what happened next.

“If Black people just act a certain way, [they] would be afforded rights and freedom” is how Angela Lewis-Maddox, a political science professor at the University of Alabama, Birmingham, and author of Conservatism in the Black Community: To the Right and Misunderstood, describes the essence of the Black conservative experience, as articulated by Sowell and others. This is not a new phenomenon, she notes. In 1787, Jupiter Hammon, an enslaved person and a writer, addressed a crowd of enslaved people in New York. “Now I acknowledge that liberty is a great thing, and worth seeking for, if we can get it honestly; and by our good conduct prevail on our masters to set us free.” God wanted them to obey their masters and who were they to disobey God? Hammon wished for “younger Negroes” to be free but was comfortable remaining a slave because it was all he knew. But the belief that their freedom was bound up in their character and not their literal enslavement set the tone for an important theme in Black conservatism. Lack of morals, not racism or indifference or discrimination, could explain the Black condition.

“The ‘legacy of slavery’ argument is not just an excuse for inexcusable behavior in the ghettos,” Sowell writes in the National Review article. “In a larger sense, it is an evasion of responsibility for the disastrous consequences of the prevailing social vision of our times, and the political policies based on that vision, over the past half century.” Conservatives obsess over individual morals while excusing the moral failings of an entire apparatus. Black people may as well have enslaved themselves. This broadside is hardly different from the infamous “Pound Cake” speech given by comedian, TV star, and convicted rapist Bill Cosby in which he implored young Black men to pull up their pants so white people would respect them.

From the work of Sowell and Clarence Thomas, you can make out the contours of modern Black conservative ideology. Patriarchal, individualistic, and capitalistic, fatalistic in its view of racism’s persistence, Black conservatism is a sort of thwarted Black nationalism, all bleakness and bootstraps. Just as important is what Black conservatism is not: a palette-swapped movement conservatism, which tends to dislodge race from the heart of the American story. Thomas might dismiss the possibility of any remedy for racism, but racism is at the center of his politics, the source of the pessimism that has shaped his jurisprudence. And if Sowell is heavy-handed in his sermons about morality and respectability, his views still speak to a shared Black experience. 

But there are nuances within Black conservatism, as Lewis-Maddox reminds me. She puts Black conservatives in one of four general categories: First are the members of the religious right, then there are the Afrocentrists, the neoliberals, and the individualists. For each of these four groups of Black conservatives, their understanding of the role racism and discrimination plays in the lives of Black Americans frames their political leanings. Her model confounds any attempt to map the Black political spectrum onto the liberal–conservative paradigm. Many of the 40 percent of Black Democrats who identify as moderate and not liberal would fall into one or more of these categories.

The religious right, and Jackson would include himself in that group, believe that while white supremacy is partially to blame, Black inequality can also be explained by a lack of morals. Jackson believes that it only makes sense for Black people vote Republican. “If you look at the Black family, if you look at the values and principles that have guided the Black family from as far back as slavery,” Jackson insists, “we are very God-fearing, conservative people.” And in his view, the Republican Party is the only one that aligns with those godly principles. As we spoke, it became obvious that religion was the main driver of his conservatism. “It is our responsibility to do just what the word of God says,” Jackson says, and supporting Republicans who espouse organized religion and pay lip service to small government ideals is the way to do it. “We are not supposed to go to the government first for our needs,” he told me. “We’re supposed to go to the Church.”

Naturally, Jackson isn’t alone in thinking that God-fearing Black people belong in the GOP. “When I think to myself—how do I reconcile being Black and being Republican? I reconcile myself first as a child of God,” Danielle Robinson, a Black woman from North Carolina told a Raleigh ABC News affiliate in August. “Black is beautiful, being Black is excellent, and at the end of the day, Black people do not have to continue sacrifice what seems like Blackness, or the direction of what Blackness should be in exchange for real results for our community.” To this we could include all the Black pastors who were photographed in the White House praying for Trump. Philpot notes that the perspective of those who support the Republican Party because of their personal religiosity tends to lean more towards the white evangelical tradition of Christianity.

The Afrocentric conservative squares the blame for the condition of Black people on the dominance of whiteness. They are likely to be what we call “Hoteps”—the name is from an Egyptian word that means “at peace.” These are Black people who practice respectability politics and have socially conservative views. With a strong racial identity, they value the patriarchal family. You can find them on the internet opining about Black people as kings and queens, but only in the patriarchal sense. But because they see white racism as the main reason for the Black condition, they’re unlikely to vote for Republicans. Nonetheless, their traditional views place them squarely in the conservative tradition.

Neoliberals tend to be wealthy and gravitate toward a conservative party that favors rich people. Herman Cain, who passed away from the coronavirus in July, was a Republican stalwart. The former CEO of Godfather’s Pizza, Cain came to prominence during the 2012 presidential election when he ran on a platform that Trump would repeat four years later: His supposed business acumen would help him become an exemplary candidate. Never mind that the federal tipped minimum wage is stuck at $2.13 an hour thanks, in part, to a lobbying effort he led in the 1990s. Cain popularized a flat tax rate plan and his, ahem, unconventional ways helped make him a serious contender for the White House.

He was the perfect foil for Barack Obama; how could anyone charge the Republicans with racism if the party was boosting a Black man for the top of the ticket? But in late 2011, Cain suspended his campaign, brought down by several allegations of sexual harassment. As a testament to just how badly the GOP needs visible Black supporters, and how shallow the bench is, Cain was appointed to co-chair Trump’s Black Voices for Trump coalition in November 2019. It was unclear how the group planned on drawing Black voters into the fray, but Cain boosted Trump for reelection through the beginning of the pandemic and the massive uprising that spread through the country. In June, Cain attended a Trump rally in Tulsa, Oklahoma. The state was seeing an uptick in coronavirus cases and Tulsa’s public health director had asked the Trump campaign to postpone the rally. Reeling from the controversy over his gassing of protesters in Washington, DC, for an awkward photoshoot in front of a historic church, Trump refused.

Cain was photographed at the rally shoulder-to-shoulder with other maskless Black Trump supporters. Less than two weeks later, in early July, he announced that he’d been hospitalized with the coronavirus. He died on July 30. Cain’s public relations team continues to tweet from his account and write blog posts downplaying the virus and supporting Trump. It’s unclear whom these posthumous posts are for. The Republican Party has forgotten about him.

Individualists see themselves as an American first and don’t feel particularly bound to race. “I work hard. I did all this and it didn’t have anything to do with my race,” Lewis-Maddox says, explaining their thinking. Candace Owens best fits this bill. “It was because America is a great country and America is a land of opportunity and everybody can get whatever they want if they just work hard,” Lewis-Maddox says. It also doesn’t hurt the self-interested that the overwhelming majority of Black people support the Democratic Party. “If you are one of the handful of Trump supporters who’s African American, you’re guaranteed at least some screen time,” Philpot says, “if not a position of prominence.”

It appears that Jackson also fits at least partially into this final category. An investigation of his work by the Tampa Bay Times that appeared this summer found that there are few active members of the caucus he says he heads, and that Jackson seems to have operated without much oversight, much less organizational structure, even though he brags about representing 60,000 registered Black Republicans in this crucial swing state. Jackson did not respond to a request for follow-up comment on this discrepancy. Nonetheless, as one of Trump’s self-appointed Black champions, he attracts some media attention, basically by dismissing racist statements by Republicans like Gov. Ron DeSantis and Donald Trump. It’s essentially part of the job description. 

Black Republicanism can be located in this taxonomy but the practical realities of being an elected Black Republican right now mean that the language of Black conservatism is being used to address white audiences. This was the case at the Republican National Convention in August, during which Black political figures were trotted out less to pull in Black voters than to assure white moderates that their party had not gone full Confederate.

Tim Scott, the senator from South Carolina, was among them. Scott, soon to be the last Black Republican in Congress, was elected in Sen. Lindsey Graham’s South Carolina, and his constituents are overwhelmingly white. In his various defenses of the president, Scott hems and haws. When Trump refused to denounce the Proud Boys, a far-right extremist group, at the first presidential debate in 2020, Scott offered the president a lifeline. “I think he misspoke. I think he should correct it,” he said. “If he doesn’t correct it, I guess he didn’t misspeak.” At the RNC in 2012, Scott spoke of learning to “think his way out of poverty.” He said, “My journey has been filled with potholes—I hit them all. But in America a kid born anywhere at anytime can rise to the level that he or she wants to go.” Scott isn’t blind to racism—he opposed Trump’s nomination of Thomas Farr to the federal judiciary because of Farr’s work with arch-segregationist Jesse Helms—but his politics are shaped around avoiding direct confrontation with it. “Education and hard work are the closest things to magic,” he once said.

Then there’s Daniel Cameron, Kentucky’s Republican attorney general who was tasked with deciding whether the Louisville police officers committed a crime when they shot and killed Breonna Taylor, a 26-year-old Black woman, while she slept in her bed. After a grand jury indicted one of the officers involved for wanton endangerment for shooting into Taylor’s neighbors’ apartment, Cameron, a Mitch McConnell protege, earned praise from the president, the most important member of his white audience. Cameron also spoke at the RNC in August.

There are exceptions. Appearing on the What the Hell Is Going On? podcast hosted by conservatives Marc Thiessen and Danielle Pletka, Rep. Will Hurd, a Texas Republican, laid out a history of structural racism that would not have been out of place in an anti-racist consciousness-raising session:

In San Francisco, after World War II, there were places where African Americans weren’t allowed to get FHA loans. There were communities that were built that weren’t allowed to have black people apply to try to rent those homes. This is what everyone would consider liberal progressive San Francisco, and we’re talking ’40s and ’50s. And you can fast forward to 1968, where a lot of those things were still going on and that stuff was still happening even in the ’70s. So, while a lot of those things have been taken off the books today, the ramifications of those previous decisions are still having an influence.

But Hurd isn’t running for reelection. He’s giving up his seat after this, his third term.

Michael Steele was the first Black man elected in a Maryland statewide office as lieutenant governor. He has endorsed Joe Biden but he has not yet given up on the Republican Party. He still imagines the GOP can still be wrested from the president’s grip. “In order to fight for the future of the GOP, it starts by defeating a president who is an anathema to the very principles that were so inviting to me as a young man,” Steele told the Washington Post’s Jonathan Capehart in August. “Trump’s full-throated embrace of conspiracies and white nationalism; his encroachments on our constitutional values; his efforts to undermine the integrity of our voting system and the seemingly interminable fear most Republicans have of a tweet is enough.”

As Steele tells me, “It’s been frustrating to me to see the party resorting to its old tactics.” But maybe the party isn’t resorting to old tactics. Maybe after all these years, it’s openly embracing what’s been its core principles since the Southern strategy. In the end the question is not if it’s a place that Black conservatives could ever consider home, it is why some could imagine it would ever change. 

I asked Jackson to give me the spiel he’d give to a potential Black voter. “For 60 years we’ve been promised these things,” he answered. “In less than three years, a white president, not a Black president, a white president was the one to actually give it to us.”

This talking point is the fallback for most Black people who support Trump, and it’s the one the president has emphasized relentlessly, as recently as during the last debate. They tout the First Step Act, a bill he championed and signed into law that aims to reduce sentences for some inmates, his success in securing funding for HBCUs, and the creation of economic opportunity zones, a program that allows investors to save on taxes when building in low-income neighborhoods. The criminal justice reform bill has been criticized for failing to meaningfully address mass incarceration, and opportunity zones have been widely disparaged as a boon to the wealthy, not to the poor. The bill that granted funding for HBCUs had been negotiated by Congress for months before the president signed it.

But even though he has campaigned for him, Jackson has lost some of his enthusiasm for Donald Trump. When he explained when his disillusionment began, I was surprised. Surely, it was when the president refused to do anything to get a handle on the pandemic, which has had a disproportionate impact on Black and Brown communities. Or the economic collapse that his inaction spurred, which has also fallen disproportionately on Black and Brown communities. Or when George Floyd was killed by a white police officer who pressed his knee into his back for nearly nine minutes, and Trump responded to the mass protests with tear gas and federal troops. It turns out, it was much earlier than that. “I traveled across in all 67 counties of the state of Florida for him,” Jackson says. “I did it all. Then Omarosa came in with him and then I wished to God that I had never gotten behind him.”

Wait. What?

The Omarosa? The Omarosa Manigault Newman who had been a contestant on The Apprentice and gone on to a White House job? Though a long-time Democrat, she joined Trump’s campaign as the director of outreach for African Americans and then his administration in the Office of Public Liaison. “I realized very quickly that she was not going to be the voice of reason between him and the Black community,” Jackson says of Newman. “It was all about her.” Jackson could not fathom why any Black voter would take Trump seriously if he thought Omarosa was the best person for the job. “She didn’t give a damn about Black America,” Jackson notes, “which in retrospect shows that [Trump] didn’t give a damn about Black America.” Newman was fired in December 2017 after less than a year on the job. She claimed Trump was a racist, and that she’d heard tape of Trump using racial slurs. To Jackson, Trump relying on someone who was more interested in self-promotion than actual political outreach proved that wasn’t really interested in reaching out to Black voters. It revealed a stunning lack of self-reflection.

Jackson says the president’s pandemic response and his reaction to the protests have made it close to impossible to convince Black people to vote for him. “You can’t just come at Black people in such a tone and manner that makes it seem as if you’re not being sensitive to the needs of our community,” Jackson says about the way Trump has threatened protesters and sent racist tweets during the uprising. “And furthermore, you have to understand that there is such a little thing called institutional racism.”

Jackson is slippery on this score. He uses the phrase “institutional racism” and yet does not think that Trump, a real estate mogul once sued by the Justice Department for discriminating against would-be Black tenants, is racist. Instead, he excuses Trump’s racism as a function of his privileged upbringing—as if racism weren’t embedded in the advantages with which Trump was born. Jackson says the president is someone who “never had to deal with” this in his life and thus does not know how “to be sensitive to it.” Despite it all, Jackson is still voting for Trump. “I’m not voting for the person,” he assures me. “I’m voting for the principles of that party, of my party, of the Republican Party.” 

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