E189 | DEI in the Crosshairs: The Ivy League, Silicon Valley, and the Rewriting of the “American Dream”

Summary

• Trump’s three executive orders turned DEI from a corporate compliance issue into a federal enforcement risk. On his first day in office, he signed “Ending Radical and Wasteful Government DEI Programs and Preferencing”; the third order directly rescinds the Johnson administration’s 1965 affirmative-action requirements for federal contractors and directs the attorney general to “identify the most egregious DEI practitioners” for civil-compliance investigations. Meta and Google have already cited changes to procurement standards as they move to end their hiring targets for women and minorities; Costco is one of the few companies still holding the line.
• Universities are the most vulnerable counterparties. After Columbia lost $400M in federal funding for “failing to protect Jewish students,” it quickly capitulated—banning masks, allowing campus police to arrest students, and installing an outside monitor in its Middle East, South Asia, and Africa studies departments. At the time of publication, Harvard had already had $2.2B in research funding frozen and was suing the government. The guests judged that the backlash had “not formed an institutionalized, organized force of opposition,” while legal remedies are unlikely to work with the Supreme Court under conservative control.
• 思骋’s core judgment: DEI is a smokescreen that can contain anything. The DC plane crash and California wildfires were both blamed on DEI. Republican voters are “very supportive” when asked concretely about fair hiring and parental-leave rights, but after politicians and media activate a priming cue, they immediately reverse their original support: “Now it looks like this policy is working pretty well.”
• Simon’s attempt to demystify Silicon Valley’s rightward turn: the alliance between Silicon Valley and the progressive left during the Obama era was not the whole of Silicon Valley politics. Its political roots reach back to the 1960s New Communalists—from political mobilization to technical solutions, from anti-establishment politics to decentralization, “exactly the same” as today’s crypto ideology. In the 1988 Stanford culture wars, Peter Thiel founded The Stanford Review, one of the important strongholds of Silicon Valley’s right.
• Neither guest defends DEI as currently practiced, but both oppose Trump-style dismantling. DEI implementation has indeed become rigid: research shows that coercive diversity training creates negative incentives and “increases resentment,” while Lauren Rivera found that selectively applied hiring tests “expand bias rather than eliminate it.” Simon supports a purely reparative approach, but concedes that “in the current political environment, it is unlikely to take shape.”
• Housing is the hidden thread connecting DEI, race, and Silicon Valley. Tech clusters push up housing costs, producing homelessness and gentrification, while the root of the supply shortage lies in racially discriminatory zoning laws and redlining: “I climbed the ladder myself, and now we’re kicking it away.” The left cannot find the political momentum to challenge entrenched interests in technology and finance.
• The closing risk assessment: 思骋 warns that eugenic thinking is “gradually returning to the mainstream political stage,” and that “America’s democratic system is backsliding; whether it can still be considered a liberal democracy is now a very serious question.” The only optimistic variable is that disagreements among Musk, Trump, Rubio, and other institutional conservatives “may prompt some policy pullback by the current administration.”

Deep dive

1. Three Executive Orders: DEI Becomes a Federal Enforcement Target

• Simon lays out the opening salvo: on his first day in office, Trump signed “Ending Radical and Wasteful Government DEI Programs and Preferencing,” giving federal agencies 2 months to shut down all DEI offices and programs with “discriminatory” features and terminate “social engineering” equity plans. “What exactly counts as social engineering? The order doesn’t say.” Procurement decisions must also exclude companies’ IDEA metrics.
• The second order targets “gender ideology,” which is likewise undefined: it removes related statements and policies, bars federal funds from supporting them, and prohibits transgender people from using bathrooms corresponding to their gender identity. The third, “Ending Illegal Discrimination and Restoring Merit-Based Opportunity,” rescinds President Johnson’s 1965 executive order—the foundation of affirmative-action requirements for federal contractors to recruit more minorities and women—and directs the attorney general to launch potential civil-compliance investigations into the “most egregious DEI practitioners.”
• The latest enforcement example: the Equal Employment Opportunity Commission sent investigation letters to 20 organizations, including the largest law firms, accusing them of “potentially discriminating against white people in hiring” and demanding the names, gender, race, schools, and GPAs of every new hire over the past 10 years. Simon’s verdict: “This is extremely ridiculous.”

2. Politics Leads, Business Responds, Education Is “Meat on the Chopping Block”

• Simon’s ecosystem map: the DEI offensive is driven by politicians, reaches back to the culture wars of the 1980s, and mobilizes conservative elites in Silicon Valley. Meta and Amazon have cited federal rules to cut DEI programs, while Costco continues to hold the line; universities are “under siege.” Opposition exists across social and traditional media, “but whether it has formed an institutionalized, organized force of opposition—I don’t think it is sufficient.” The Democratic Party “lacks a very good way to respond.”
• The tactics are extreme: law firms are barred from having their lawyers enter federal buildings to take depositions, and federal contractors are prohibited from doing business with them—“fundamentally cutting off their ability to do business.” After losing $400M, Columbia accepted “extremely cruel demands”: banning masks that conceal identity, allowing campus police to arrest students, and bringing in an outside monitor to oversee its Middle East, South Asia, and Africa studies departments because those programs had stood with pro-Palestinian students over the past year. “They were hit with a sledgehammer.”
• The judicial route is constrained: with the Supreme Court controlled by conservatives and the courts operating slowly, “it is very difficult to use the judiciary to constrain Trump’s swift and aggressive executive actions. There really aren’t many ways to fight back.”

3. DEI as Scapegoat: Everything Gets Poured Into It

• 泓君 asks what the $400M cut was actually targeting, prompting an important distinction: attacks on NIH and NSF funding are “actually a separate matter” from DEI, but both are being executed by DOGE under Musk, so “the governing principles are appearing in an intertwined way.” If one tries to use a single ideological focal point to interpret events, “there is no way to capture these threads with complete accuracy.”
• Simon’s scapegoat thesis: after the DC plane crash, Trump said, “This must have been caused by DEI”—the previous administration had allegedly overemphasized diversity in hiring air-traffic controllers and relaxed safety standards. Conservatives also blamed the California wildfires on DEI. “For years, conservatives have used DEI as a smokescreen; anything can be poured into it.”

4. DEI’s Genealogy: From Kennedy’s Executive Order to “Diversity as a Competitive Advantage”

• 思骋’s history lesson: the policy’s antecedents stretch back to 19th-century support for veterans and widows of fallen soldiers. In contemporary usage, DEI often means affirmative action and can be traced at least to Kennedy’s Executive Order 10925, which required government contractors to make hiring and promotion decisions without regard to race, faith, or color. Lyndon B. Johnson later expanded the framework, and George H. W. Bush signed the Americans with Disabilities Act in the 1990s.
• The key paradigm shift came in the 1980s, when Reagan systematically dismantled the legacy of the civil-rights movement and forced affirmative-action advocates to change their pitch. Diversity moved from a “legal requirement” to a “competitive advantage”: a diverse environment was said to improve business performance and generate more intellectual friction. 思骋’s addendum: diversity was no longer grounded in moral principle itself, but had to be tied to higher corporate profits and better university education. In litigation, universities argued that diversity improved teaching quality, not that diversity was intrinsically a moral good.

5. Why Asians Feel They Are Not on the List

• 思骋 begins with the history of segregation: in the 1950s, Black and white students could not attend the same schools, Black passengers were expected to give up their seats on buses, and restaurants barred Black customers. As he remembers it, the civil-rights movement was ignited by a Black woman who refused to give up her seat. “Every page of American history is written with racism.” But if DEI favors Black people while excluding Asians with higher scores, why?
• Simon’s answer: DEI originally meant compensation for historical inequality. Once that compensatory narrative faded in the 1980s and was replaced by “diversity is our strength,” the beneficiary pool expanded beyond Black and Indigenous people. International students unfamiliar with this history can therefore easily feel: if this is about diversity, why am I not part of the agenda? At least part of the perception gap comes from there.
• 思骋 adds balance: the groups covered by DEI are far more diverse than the Chinese internet imagines. Veterans and people with disabilities are included; Coolidge once awarded extra points to veterans taking civil-service exams, “a little like preferential admission for ethnic minorities in our country.”

6. The Origins of Silicon Valley Politics: New Communalism and Peter Thiel at Stanford

• Simon rejects treating the Obama era as an “unshakeable truth.” Silicon Valley’s political culture originated in the New Communalist movement of the 1960s: California youth disillusioned with urban protest went into the mountains to form communes, shifting “from political mobilization to the search for new modes of communication,” using decentralized, anti-establishment technology to eliminate inequality. In the early internet’s anonymous, virtual imaginary, “government didn’t need to exist and might even obstruct technological progress.” 泓君 puts it bluntly: “Isn’t that exactly the same as today’s crypto ideology?” Simon confirms that this has always been a recurring political-philosophical thread in Silicon Valley.
• The West Coast’s main battleground in the culture wars of the 1980s was Stanford. In 1988, progressive students successfully abolished the required Western Civilization course on anti-Eurocentrism and anti-Patriarchy grounds. Around the same time, Peter Thiel, then still a student, founded The Stanford Review, which became the most important base for conservative student mobilization and ideological critique—and one of the important strongholds of Silicon Valley’s right, distinct from the Republican establishment.

7. Reagan’s Co-optation and Dog Whistles: A Rhetorical Production Line Still in Use

• 思骋’s mechanism analysis: the New Left’s 1960s pursuit of individual rights created the cultural soil for Reagan. Evangelicals had been politically marginal before the 1980s, but Reagan “very skillfully incorporated religious conservatives into the Republican mainstream,” turning criticism of sexual liberation and social atomization into right-wing ammunition.
• The model dog whistle was the campaign ad “Morning in America”: a white middle-class family’s day, a large suburban house, a dog being walked, and not a single person of color in the entire film. “Everywhere you looked, there was a racialized imagination,” because under redlining, the suburbs were already the preserve of affluent whites. “Law and order,” apparently neutral language, in practice encoded the mass incarceration of Black people; minor offenses such as marijuana use were enough to send Black teenagers to prison en masse.

8. The Rhetoric of Cutting Benefits: Trickle-Down Economics and the Red-State Voter Paradox

• 思骋 connects Reaganomics to the present: behind tax cuts, welfare reform, and law-and-order politics lies Trickle-Down Economics—cutting social benefits and transferring tax revenue into the pockets of the wealthy. “That is still the economic policy of the Trump administration today.” When conservatives say there is too much debt, they mean cutting public benefits and taxes alike, with the aim of “improving the quality of life for the upper-middle class and the 1%,” while “inventing a very attractive rhetorical system to cover it up.”
• 泓君’s question exposes the contradiction: white working-class voters are precisely those most dependent on these benefits. 思骋 acknowledges that the Affordable Care Act enjoys very high approval in red states: “If you don’t call it Obamacare and simply tell people what it contains, most people will raise their hands and agree.” In deindustrialized red states, these policies are a lifeline. That is the point of dog-whistle politics: to make white voters associate “welfare” with poor Black people in big cities rather than with their own health insurance and their children’s schools.

9. Silicon Valley’s Rightward Turn: Regulatory Fractures and DEI’s Own Backlash

• Simon’s structural explanation: the Obama-era alliance rested on the idea that global democratization depended on Twitter and Facebook, as well as favorable immigration policy. But the regulatory question was never resolved—how much authority the state should exercise over technology’s ethics and fairness is not something a Democratic administration and Silicon Valley elites could necessarily settle with ease.
• 思骋 identifies an internal structural cause: mandatory diversity training often contains negative incentives—“if discrimination occurs, the company will pay a price.” Research shows that training framed as “if you don’t do this, you can’t get hired” increases rather than reduces resentment. In Northwestern professor Lauren Rivera’s How Elite Students Get Elite Jobs, selectively applied math tests meant that when white candidates performed poorly, “the team would barely pay attention,” while weak scores from Black or female candidates drew close scrutiny. Decision-makers selectively used the results, consciously or otherwise, “expanding bias rather than eliminating it.”

10. Should DEI Be Abolished? A Contradiction That “Seems to Leave No Way Out”

• Yiwen asks the question directly; 思骋 acknowledges that Silicon Valley has indeed gone “too far.” Asian Americans may be passed over for promotion despite being the strongest performer in a cohort that includes minority women, while Asians can feel reverse-discriminated against in education. “Everyone’s understanding of fairness is very different.” Simon describes the bind: DEI implementation has become rigid and even counterproductive, but if the left criticizes its execution now, “you start worrying whether you are helping the Trump administration, so many constructive discussions cannot emerge in this environment.”
• Simon states his position with its conditions intact: “I support a purely reparative approach”—compensation for historical injustices inflicted on Black and Indigenous people in education, healthcare, and other areas fundamental to survival and development. But the Democratic Party “has already trained a large number of establishment-friendly elites” who lack the capacity to correct course, and Trump’s dismantling makes it impossible to build this vision anew. “Could such a plan take shape in the current political environment? I don’t think it is very likely.”
• 思骋 identifies two killer questions from conservatives: should reparations go only to Black Americans whose ancestors were demonstrably affected by slavery? Should there be a time limit—“reparations for the next 25 years, then stop”? “I don’t know whether the left has a very good answer on this.” The discrimination faced by Black people in inner cities stems not only from slavery but also from 2 or 3 subsequent centuries of discrimination that was never codified in black and white; the damage is fundamentally difficult to measure.
• The left’s self-critique is not absent. 思骋 recommends Georgetown philosophy professor Olúfẹ́mi O. Táíwò’s Elite Capture, which argues that diversity politics overfocuses on individual experience and elite institutions. The beneficiaries are often “the already relatively affluent segment of the Black community”; once children from culturally elite families enter corporate boards and top universities, the policies they advance benefit people with backgrounds like their own and “cannot extend benefits to a broader population.”

11. The MAGA Coalition and the Return of Eugenics

• 思骋’s risk assessment: right-wing activists have used opposition to DEI to unite cultural conservatives, fiscal conservatives, and white nationalists who believe in the conspiracy theory that “white America is being replaced by people of color,” creating the ideologically vast MAGA coalition. DEI is a smokescreen, while the contrast in the questioning shows how a priming cue can easily make Republican voters reverse their positions on specific affirmative-action policies they originally support.
• The deeper warning: “Historically, the American right—especially these technology elites—has embraced eugenic ideas: that there are IQ differences between races and insurmountable differences between individuals. That thinking is gradually returning to the mainstream political stage, and I think that is extremely dangerous.”

12. Housing: Linking Tech, Race, and Homelessness

• Simon follows the chain, with 泓君 challenging him in real time. 泓君 cannot see why San Francisco’s large homeless population should be “directly related” to tech companies, arguing that city policies to build shelters attract people. Simon’s answer: shelters are a compensatory measure that causes homeless people to cluster, not the reason homelessness exists. Tech clusters drive up home prices and rents; locals who can no longer afford housing cannot return to a stable, housed life after a setback. The tech workforce is also large enough to sustain its own ecosystem—chain coffee shops, for example—and “does not always give back to the local native economy.” Seattle shows the same pattern.
• Simon offers an example worth preserving: a friend in tech moved to work in a cluster and was asked what the area was like. “Everything is great, except there are too many homeless people.” “He never forms the connection that the industry he works in is directly related to the emergence of homelessness in the area,” because depoliticized ideas about technology are widespread among Chinese tech workers.
• 思骋 connects the supply shortage to racial history. Democratic states have the highest housing costs—New York, San Francisco, Seattle—while, as 泓君 recalls, Austin’s median home price was perhaps $200K-$300K. The roots lie in the mortgage system that began with the New Deal and systematically excluded Black people from middle-class wealth accumulation, combined with zoning laws designed to protect home values. “In San Francisco, high-rises are concentrated in one small area; middle- and upper-middle-income people who already bought small houses do not want newcomers blocking their ocean views or lowering property values.” “I climbed the ladder myself, and now we’re kicking it away. This is also extremely common among tech workers.” The left “has a very hard time finding the political momentum to persuade these vested interests,” so “there is no obvious solution.”

13. From the War on Poverty to the War on Crime: A Vicious Cycle Seeded in the 1960s

• Simon recommends Yale historian Elizabeth Hinton’s From the War on Poverty to the War on Crime. The 1960s progressive movement bears direct responsibility for today’s mass incarceration: as Black communities erupted in unrest, the Great Society’s reform agenda rapidly shifted from welfare construction to crime control. LBJ’s 1965 Law Enforcement Assistance Act marked the first time the federal government directly funded local police; “law enforcement, rather than fundamentally improving social welfare, became the core of the anti-poverty strategy.”
• Clinton’s 1990s school-to-prison pipeline sent police into inner-city public schools and imposed zero tolerance. “You’re late, you get into a fight with a classmate, and you’re immediately taken to prison. Your life is ruined; when you get out, all you can do is join a gang or shoplift.” The answer to crime is not more policing: “You need to increase education funding, make inner-city public schools better, and get the entire inner-city economy moving.”
• 泓君’s firsthand observation brings the point home: public high schools in better-off parts of Silicon Valley have college-going rates of roughly 50%. During the pandemic, friends volunteering in Oakland found many elementary and middle-school students bringing guns to school. Their only reason for attending was “to get the public-school lunch, because they couldn’t afford to feed themselves.” When schools closed, someone had to distribute lunch; “otherwise these kids would have nothing to eat.” Simon’s conclusion: public schools are funded by property taxes, and the gap between Palo Alto and inner-city Oakland locks housing, education, and race into a single cycle. Conservatives’ charter-school solution “cannot solve the problem at its root.”

14. At a Historical Turning Point: Consensus Breaks, and Any Prediction About the Future Will Probably Look Foolish

• 泓君 observes that Chinese people often treat diversity as a taboo corporate topic, while Americans raised locally speak openly about how “diversity can improve productivity”—a legacy of the 1980s. Today, companies cutting DEI “still have to stand on the moral high ground and invent a perfect justification”; the political context is turning again.
• 思骋’s left-wing self-assessment: “Every process of democratization is a process of consensus breakdown, and consensus breakdown is not necessarily a good thing.” The key is not to find the best defense of the old system at this moment, but to recognize that “there is currently no formed, organized left-wing force capable of steering the debate over DEI toward a new, more progressive democratic consensus.”
• 泓君 looks to historical self-correction over eugenics for optimism. Stanford’s first president became a forceful eugenics advocate late in life; in the 1920s and 1930s, many states adopted eugenics policies, allowing disabled people to be sterilized with the support of progressive Supreme Court justices. “But in the end, they were corrected. Perhaps we can maintain some degree of optimism.” 思骋 rejects any softening: “We should not minimize the danger of this moment. America’s democratic system is backsliding.” The more optimistic possibility is that disagreements among Musk, Trump, Rubio, and other institutional conservatives “may, to some extent, prompt policy pullback by the current administration.”