Evidence from Trump’s second term shows a mixed but ultimately retaliatory and selective posture toward business leaders and firms, contradicting Chamath’s claim that “we’re not going to ostracize people” or “play favorites.”

Where the prediction looks partly right:

• Trump has actively courted many major tech leaders, including some who were previously framed as political adversaries:
  • The second inauguration featured prominent tech CEOs and investors — including Meta’s Mark Zuckerberg and OpenAI’s Sam Altman — as donors and VIP attendees. (en.wikipedia.org)
  • On January 21, 2025, Trump stood alongside Altman, Larry Ellison, and Masayoshi Son at the White House to unveil Stargate, a joint venture led by OpenAI/SoftBank/Oracle to invest up to $500B in AI infrastructure — described by Trump as the “largest AI infrastructure project in history.” (en.wikipedia.org)
  • A July 15, 2025 AI-and-energy summit including Altman, Zuckerberg, Nadella, and Pichai, and a September 4 White House dinner with over two dozen tech leaders (Zuckerberg, Altman, Gates, Cook, Pichai, Brin, etc.) showcased close engagement and praise for Trump’s pro-business, pro‑AI agenda. (reuters.com)
  • Trump’s AI policy (EO 14179 and his AI Action Plan) is explicitly designed around industry partnerships and deregulation, with OpenAI and other firms providing input — another sign of access rather than ostracism for these particular companies. (en.wikipedia.org)

But key actions clearly do ostracize and punish disfavored firms/figures:

• Targeted retaliation against specific law firms for political reasons:

  • On March 6, 2025, Trump signed Executive Order 14230 barring the federal government from using the law firm Perkins Coie, suspending its attorneys’ security clearances, barring them from federal buildings, and ordering reviews aimed at terminating government business with its clients. The order explicitly tied these sanctions to Perkins Coie’s past work for Democratic figures (e.g., Hillary Clinton), as part of a broader Trump campaign against firms tied to investigations of him. (en.wikipedia.org)
  • A federal judge later struck down that order as unconstitutional, calling it retaliatory and aimed at suppressing dissenting viewpoints, noting it used state power to intimidate legal advocates of opposition causes. (politico.com) This is textbook political ostracism of a specific business entity.

• Retaliatory threats against Elon Musk’s companies:

  • Once close allies, Trump and Elon Musk fell into a public feud in mid‑2025 over Trump’s spending bill. In response to Musk’s criticism and threats to disrupt NASA service with SpaceX’s Dragon spacecraft, Trump publicly threatened to terminate Musk’s “governmental subsidies and contracts”, framing it as an easy way to save “billions and billions of dollars” in the budget. (twitter.com) This is a direct threat to punish a specific business leader and his companies for political opposition.
  • Around the same time, Trump held a White House tech/AI dinner with almost every major Silicon Valley leader except Musk; AP explicitly noted Musk’s “public fallout” with Trump and his notable absence, while rivals like Altman were present. (apnews.com) That selective access is the definition of “playing favorites.”

• Selective exclusion based on ideology in federal contracting:

  • In July 2025, Trump signed an executive order instructing agencies to bar AI vendors with “partisan bias or ideological agendas” — aimed at eliminating “woke AI” from federal contracts and requiring screening for ideological content in AI systems. (ft.com) While not always naming individual firms, it sets up a system in which companies with certain viewpoints can be excluded from federal business, again undermining the idea of an even‑handed, non‑retaliatory posture.

Assessment:

• Chamath’s narrower intuition — that the Trump White House would be open to deals even with previous tech-world critics like Zuckerberg and Altman — has been borne out: Meta and OpenAI enjoy high levels of access, partnership, and praise.
• But his broader claim that the administration “is going to turn a totally new page,” not ostracizing people or playing favorites, has clearly failed. The administration has:
  • Used executive orders to single out particular firms (Perkins Coie and others) for bans and sanctions because of their past political work; and
  • Publicly threatened to pull government contracts and subsidies from Musk’s companies in direct response to his political criticism, while simultaneously rewarding more aligned tech leaders with access and favorable treatment.

Because the prediction was framed as a general stance (“we’re not going to ostracize people… we’re not going to play favorites”), these repeated, targeted retaliatory actions against specific firms and individuals mean the prediction did not come true overall.