The Bulwark Podcast

Episode: David Kirkpatrick: Trump's Self-Enrichment

Date: August 19, 2025
Host: Tim Miller
Guest: David Kirkpatrick, Staff Writer at The New Yorker

Episode Overview

This episode delves into the explosive reporting by David Kirkpatrick on the scale and mechanics of Donald Trump’s financial self-enrichment during and after his presidency, with a special focus on the intersection of Trump’s business interests, foreign entanglements—especially in crypto and real estate—and American politics. The discussion contextualizes Trump’s activities within historic and global standards of corruption, explores whether a new precedent is being set for self-dealing at the highest levels of U.S. government, and examines whether any of this crosses the line from “undignified” to outright kleptocracy.

Key Discussion Points & Insights

1. Diplomatic Optics and Trump’s Foreign Relationships

[01:38 – 04:42]

• The episode opens with commentary on recent White House meetings with European leaders and Ukrainian President Zelenskyy.
• Kirkpatrick: “The Europeans showed up with a mind to flatter Trump. Those pictures suggest that was successful.” ([02:16])
• Despite affable optics and attempts to sway Trump, his continued public praise of Putin and skepticism of Ukraine’s plight signals little substantive diplomatic progress.
• The convoluted arrangements of “security guarantees” for Ukraine are discussed as a way to sidestep directly invoking NATO’s Article 5.

2. The Middle East “Realignment”: From Democracy to Deal-Making

[04:42 – 08:02]

• Conversation shifts to the U.S. pivot away from democracy promotion toward transactional relations with Middle Eastern autocrats.
• Kirkpatrick: “Even during the Arab Spring, when the U.S. was vigorously promoting democracy, that was always in tension with its simultaneous alliance with many of the authoritarians around the region. ... The U.S. is comfortable with the status quo.” ([06:22])
• The balance between U.S. values versus interests is seen as more candid under Trump but not fundamentally new; the real difference is the scale and personal nature of Trump’s profiteering.

3. Quantifying Trump’s Presidential Profits: The $3.4 Billion Estimate

[08:02 – 10:26]

• Kirkpatrick details his methodology: tracking all Trump-family income streams tied to the presidency, especially those dependent on his position and influence.
• Key Fact: Kirkpatrick’s estimate: $3.4 billion, with the majority from crypto-related enterprises. About $2.5 billion is tied to crypto deals.
• Notable mechanism: Real estate projects (Oman, Dubai, Vietnam), direct sales to supporters (merch, NFTs), and various crypto ventures.

4. The Debate: Corruption, Kleptocracy, or “Self-Enrichment”?

[11:17 – 14:44]

• Miller: “Enriching yourself off public service is corruption, even if it doesn’t change what your policies are, right?”
• Kirkpatrick: “I... went out of my way not to use the word ‘corruption’ here ... I don’t think anybody has evidence of a quid pro quo... It’s undignified... but let’s be careful.” ([11:17–11:45])
• The timing and scale are “novel”—direct family enrichment during rather than after holding power.

5. How the Trump Family's Self-Enrichment Works

[14:44 – 21:25]

• First term: The hotel-influence concerns (“Trump Hotel lost money during his four years in the White House... it’s done better as a Waldorf-Astoria.” [14:54])
• Second term: “Nothing like this in the first term... The acceleration in money-making happened shortly after he left the White House the first time.” ([15:45])
• Not merely book deals or speaking—now direct deals with foreign governments (Vietnam, Oman, Dubai) and massive, opaque crypto transactions.

6. Crypto: The Biggest Bucket of Enrichment

[21:25 – 32:58]

• Crypto-related income streams:
  • Meme coins
  • Trump NFTs (digital baseball cards)
  • World Liberty Financial (Stablecoin project)
  • “American Bitcoin” (more closely tied to Trump sons)
  • Trump Media & Technology Group (Truth Social, now tied to crypto ETFs and Bitcoin reserves)
• Miller: “The biggest nut on here... your estimated gain of 1.3 billion is based on just the stockpile of bitcoin” from 50 anonymous investors ([27:55], [47:17]).
• How it works: Meme stock sales of Trump Media, proceeds used to acquire Bitcoin and cash, essentially flipping “cult-of-Trump” stock into hard assets.
• Kirkpatrick: “They’ve turned their meme stock, which did not have a real value, into an actual liquid asset: cash and Bitcoin.” ([32:32])
• Unclear who the investors are; possible foreign involvement.

7. The Stablecoin and Foreign Ties (UAE, Binance, Justin Sun)

[34:44 – 42:46]

• Stablecoin launched by Trump-linked World Liberty Financial, with $2B+ purchased by a UAE government-controlled entity, most eventually moved to Binance, a crypto exchange founded by Chinese-Canadian Changpeng Zhao (CZ) and under SEC scrutiny.
• Kirkpatrick: “Stablecoins are often used for money laundering... Now comes a stablecoin... endorsed by the President of the United States. ... You can trust us” ([40:15], [40:43])
• Justin Sun: Chinese-born crypto entrepreneur, SEC target, now Trump’s crypto partner. Invested at least $75 million in Trump tokens, dined with Trump, investigation put on hold; himself seems to embody the “gray zone” between donor-businessman-beneficiary.
• Miller: “If [Justin Sun] was someone... under investigation for narco trafficking ... probably wouldn’t have been honored as much, maybe.” ([44:03])
• Kirkpatrick: “The timing looks pretty fishy... he puts up a bunch of money and then things go right for him with the SEC...” ([44:27])

8. Systemic Impact and the Precedent Set

[43:48 – 49:21]

• Kirkpatrick: “This is not particularly dignified. ... I think that people on both sides would agree this demeans the office... The velocity of this money-making... is the thing to watch.” ([43:48])
• On lack of clear quid pro quo: “Nobody’s got evidence yet... but the scale is new.”
• Miller and Kirkpatrick both ponder the lasting impact—has Trump “innovated” a new model for openly commodifying the American presidency? Would any norms survive?

Notable Quotes & Memorable Moments

• On the difference from past presidents:
  “Trump and his family are making this money while he has his hands on the levers of power. And that’s novel.” – Kirkpatrick [13:07]

• On the unique Trump business model:
  “As he moves from builder to television personality to political entrepreneur, he’s selling goods which are less and less substantial.” – Kirkpatrick [25:21]

• On the Trump Media Crypto Mechanism:
  “To turn that insubstantial, bubblish meme stock into an actual asset... is a neat trick, and that’s what they’ve done.” – Kirkpatrick [33:05]

• On dignified vs. undignified self-enrichment:
  “We’re still in a rule of law situation where the President has to do things that are extraordinary compared to his predecessors to try to make money on the side... he’s a real innovator in this area.” – Kirkpatrick [19:22]

• On foreign sums and Trump’s responsiveness:
  “If the Trump family is desperate to make money and broadcasting that around the world, yeah, it says, okay, I’m probably going to get something for this.” – Kirkpatrick [11:45]

• On SEC investigations and policy changes:
  “The Trump administration was on its way to roll back all the investigations into everybody in crypto before Justin Sun invested a dollar.” – Kirkpatrick [44:45]

Key Timestamps for Important Segments

• [02:16] – European diplomacy via flattery and photo-ops.
• [06:22] – U.S. posture in the Middle East: candid realpolitik.
• [08:40] – Where Trump’s money is coming from: breakdown of business, merchandise, and especially crypto.
• [11:17] – Kirkpatrick on avoiding the word “corruption.”
• [14:54] – Trump DC Hotel vs. past allegations.
• [21:25] – Don Jr.: Family now openly doing business abroad—even with foreign governments.
• [27:55, 32:32] – Explaining the meme stock/crypto conversion.
• [34:44] – Stablecoin scheme and ties to UAE/Binance/Justin Sun.
• [40:43] – Why World Liberty (“endorsed by the President”) stablecoin appeals to suspicious actors.
• [43:48] – The current “demeaning” of the presidency and what comes next.

Tone & Originality

The conversation is analytical but wry, deeply informed, and littered with Miller’s pointed sarcasm and Kirkpatrick’s careful journalistic hedging. Both speakers balance skepticism, historical perspective, and dry humor.

Final Thoughts

Kirkpatrick’s reporting reveals not just a “self-enrichment” scheme but the invention of a new, distinctly American form of kleptocratic behavior, scaled to the 21st-century digital economy and powered by celebrity, tribal politics, and global capital. The line between grift and governance has blurred, with Trump’s second act making the first look modest by comparison.

Essential Listening For: Anyone trying to grasp both the eye-watering scale and structural novelty of Trump-era profiteering, plus the challenges it poses to American democratic and ethical norms.

For the full article and more nuanced breakdowns, read Kirkpatrick’s piece in The New Yorker.