Coffee Break: Trump Insider Deals Hitting the Rocks?

Trump insider deals in crypto, AI, and drones seem to be taking a hit to match his rapidly dropping public support.

It’s fun to bet on a winner and start collecting, but when that winner’s public support nosedives, all bets are off.

Glickman and Johnson Give Us a Lens

The New York Review of Books features a discussion titled “Runaway Short-Termism” and subtitled “How has the Trump administration broken from the past century of American political economy?” that provides a useful context for looking at Trump insider deals and their larger significance.

That piece pivots off a NYRB piece “The War Over Defense Tech” by Susannah Glickman from October that focused on Palantir and Anduril and the Peter Thiel-aligned companies and their “threat to the foundations of US industrial policy.”

It also brings in Nic Johnson to discuss his April piece on Trump’s tariff-fueled trade wars.

Glickman responds to Johnson’s discussion of the Trump administration taking direct government ownership stakes in private companies by both naming a key name and describing the bigger phenomena at work with Trump insider deals.

The one-off equity deals do seem unique—not just because Deputy Secretary of Defense Steve Feinberg, formerly of Cerberus Capital Management, is staffing the Pentagon with personnel from the world of private equity and his other business networks, but also because the deals themselves are financially engineered and structured in ways that resemble private-equity practices. You take a stake, the idea goes, and then you do some work to govern and/or reform the companies that you’re taking stakes in—usually along some rubric of efficiency that makes companies seem more profitable in the short term but hurts long-term resilience and viability.

It isn’t as if these deals are reindustrializing or bolstering any particular sector. They seem to be more a matter of building private patronage networks.

Emphasis mine.

Johnson also points out something very central to the methods of these Trump insider deals while also naming a specific name:

Trump and his advisers seem similarly frustrated with the lack of flexibility that the Constitution affords the executive. But in many ways their preferred macroeconomic uses of executive power are drawing down the capital of military Keynesianism’s legacy. In the middle of the twentieth century we built bases all over the world and established the dollar as the global reserve currency—and today Trump is using all that as a weapon against the rest of the world in order to extract resources. Maybe the most telling examples are the recent “prosperity deals” he has made with Japan and South Korea, in which each country agreed to invest hundreds of billions of dollars in America. In the case of Japan these funds will flow through the “Investment Accelerator,” a fund conceived of by US Secretary of Commerce Howard Lutnick. The idea, in effect, is that Trump gets to direct this slush fund into investments that he chooses—and then America gets to keep 90 percent of the profits.

Good work if you can get it. Now let’s dive into the individuals named above as well as other key players feasting on Trump insider deals.

Trump Brothers’ Crypto Assets Falling Faster Than the Market

Let’s start with the Trump insider deals closest to home, those involving his sons Don, Jr. and Eric and crypto currency.

The Trump brothers’ were up a reported $5 billion when I covered their capers in September.

But now, things are not looking so good.

As Bloomberg reports, “Trump Family Assets Are Outpacing Crypto’s Crash.”

American Bitcoin Corp.’s shares were down more than 50% by 9:56 a.m. on Tuesday, just 25 minutes after trading started.

Projects tied to the Trump family have seen significant losses, including World Liberty Financial’s WLFI token tumbling 51% and Alt5 Sigma plunging around 75%.

The Trump family’s crypto ventures have lost over $1 billion in wealth since October, with retail investors who bought in near the peaks suffering the most painful losses.
…
It was all so spectacular that American Bitcoin quickly became the symbol of not just the crypto market wipeout of late 2025 but also the collapse of the myriad ventures that the Trump family has been promoting in the digital-currency world over the past year. For as much as broader crypto markets have sunk these past two months — roughly 25% in the case of bellwether Bitcoin — projects that are tied to the Trump family are down far, far more.
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Trump’s embrace helped boost a wide array of crypto tokens during the early months of his second term and turned the price of Bitcoin into a marker of his political success.

Now, though, what looked like a Trump premium has suddenly turned into a Trump drag, taking out one of the central pillars holding up cryptoassets and offering an indication of just how quickly confidence in these speculative markets — and even in the president himself — can dissolve.

It’s funny how that works. Especially with this POTUS and his family’s knack for staying on the shady side:

The problems, though, have gone beyond the vagaries of the broader markets. American Bitcoin has had to deal with a report that the mining machines it uses, from a Chinese manufacturer, have been investigated as a risk to US national security. Meanwhile, Alt5 Sigma, a public company that set out to buy one of the tokens issued by World Liberty Financial, has faced an exodus of executives after announcing that one of its subsidiaries had faced a criminal probe in Rwanda.

Something, something, buy crypto from dogs, wake up with fleas? I can’t remember how exactly that one went, but clearly we’re living in it.

I should also check in on the Trump Bros. drone company Unusual Machines, which I covered in October. Shareholders have just been told the happy news about the company’s first profitable quarter, I wonder if that will motivate The Motley Fool to change its “sell” rating. Other market analysts are growing more bullish on the plucky little dronemaker with the big Trump insider deals.

And while we’re talking about drones and revisiting Trump insider deals we’ve covered before, it’s time to check in on our boy Palmer Luckey, CEO of drone-maker Anduril.

Palmer Luckey’s Drones Don’t Work?

As is the case so often with Luckey, a picture is worth 1,000s of words, even if it’s a picture of words as in this Wall St. Journal headline about his company’s products:

pic.twitter.com/qxoS13lLtE

— Nat Wilson Turner (@natwilsonturner) December 3, 2025

Key points from the story:

In California, a mechanical issue damaged the engine in Anduril’s unmanned jet fighter Fury in a ground test over the summer ahead of a critical first flight for the Air Force. In August, a test involving its Anvil counterdrone system caused a 22-acre fire in Oregon. And in the exercises with unmanned boats over the summer off the coast of California, Anduril’s Lattice software struggled to command and control vessels.

Anduril’s only real battlefield experience—in Ukraine—has been marred by problems as well, including vulnerability to enemy jamming, according to former employees and others familiar with the systems in Ukraine. Some front-line soldiers of Ukraine’s SBU security service, for instance, found that their Altius loitering drones crashed and failed to hit their targets. The drones were so problematic that they stopped using them in 2024 and haven’t fielded them since, according to people familiar with the matter.

The whole article is a hoot for skeptical observers of Palmer Luckey as phrases like “(Anduril software product) Lattice has fallen far short of servicemembers’ expectations,” “Anduril’s Anvil counterdrone system crashed and caused a 22-acre fire,” and “Anduril is less prepared institutionally to do this, so they are finding their way around,” dot the text like dayglo sprinkles on a bad grocery store cupcake.

But Palmer Luckey is small potatoes compared to the Trump administration’s official “White House AI and crypto czar” David Sacks, who’s been enduring some bad media coverage of his own.

The NYT Goes After Sacks, Silicon Valley Responds

As virtually the only profitable legacy American newspaper, The New York Times still sets the agenda for much of the media, mainstream and alternative alike.

So their November 30 article headlined “Silicon Valley’s Man in the White House Is Benefiting Himself and His Friends” got quite a reaction.

Here’s some of what they had to say about Sacks’ tenure in The White House and how he and his friends have benefitted from Trump insider deals:

Mr. Sacks has offered astonishing White House access to his tech industry compatriots and pushed to eliminate government obstacles facing A.I. companies. That has set up giants like Nvidia to reap an estimate of as much as $200 billion in new sales.

Mr. Sacks has recommended A.I. policies that have sometimes run counter to national security recommendations, alarming some of his White House colleagues and raising questions about his priorities.

Mr. Sacks has positioned himself to personally benefit. He has 708 tech investments, including at least 449 stakes in companies with ties to artificial intelligence that could be aided directly or indirectly by his policies, according to a New York Times analysis of his financial disclosures.

His public filings designate 438 of his tech investments as software or hardware companies, even though the firms promote themselves as A.I. enterprises, offer A.I. services or have A.I. in their names, The Times found.

Mr. Sacks has raised the profile of his weekly podcast, “All-In,” through his government role, and expanded its business.

No event better illustrates Mr. Sacks’s ethical complexities and how his intertwined interests have come together than the July A.I. summit. Mr. Sacks initially planned for the forum to be hosted by “All-In,” which he leads with other tech investors. “All-In” asked potential sponsors to each pay it $1 million for access to a private reception and other events at the summit “bringing together President Donald Trump and leading A.I. innovators,” according to a proposal viewed by The Times.

Sacks himself responded on X.com with a tweet headlined “INSIDE NYT’S HOAX FACTORY” and his Silicon Valley pals Marc Andreessen (“David Sacks is a throwback to the era of American greatness”), Salesforce CEO Marc Benioff (“…isn’t journalism—it’s almost strategic sabotage”), Atreides Management partner Gavin Backer (“Leading in AI is good for America. And there is no way for America to lead in AI without American investors in AI doing well.”), and Sam Altman himself (“David Sacks really understands AI and cares about the US leading in innovation.”).

Gizmodo headlined their piece on the responses “Silicon Valley Ghouls Melt Down Over Report on David Sacks Business Conflicts.” So let’s just say the jury is still out on how to score this chapter of the NYT vs Trump insider deals.

There’s one more cabal of Trump insiders I need to include because they keep slipping out of my net.

A Lonely Few Warned About Feinberg at Defense

When I read Susannah Glickman name drop Steve Feinberg as the Trump 2.0 avatar of private equity’s role in transforming government grift for a new era, a chill ran down my spine.

That’s because I keep meaning to post about Feinberg but keep failing to find the right story to squeeze him into. This time there’s no excuse.

Responsible Statecraft tried to warn us about him in February:

Billionaire investor and prominent private equity firm Cerberus Capital Management CEO Stephen Feinberg’s possible ascension to the Pentagon’s No. 2 role is a textbook case of the military industrial complex revolving door.
…
A longtime military investor vis a vis Cerberus Capital Management, which holds about $65 billion in assets across various industries, possible conflicts of interests embroil Feinberg’s possible DoD ascension.

Indeed, Feinberg’s Cerberus sports a controversial investment track record in the defense sector. The head of the first Trump administration’s intelligence advisory board, Feinberg previously owned national security contractor DynCorp (now owned by Amentum) through Cerberus, where DynCorp controversially trained U.S.-backed fighters in Iraq, Liberia, and Afghanistan under his tenure. Some of Cerberus’ defense-related portfolio holdings, like Navistar Defense and TransDigm, have been notorious for price-gouging equipment for clients like the U.S. Marines Corps. And Cerberus-affiliated Tier 1 Group had infamously trained members of a Saudi hit team who killed Washington Post journalist Jamal Khashoggi in 2018.

Feinberg seems to be living up to expectations based on this headline from Forbes, “‘The Adult In The Room’: This Billionaire Trump Appointee Actually Knows What He’s Doing.”

I don’t think Forbes meant that headline to be as frightening to the average reader as it was to me.

Here’s some key passages:

Steve Feinberg. It turns out that the billionaire investor, recently sworn in as Hegseth’s deputy secretary of defense, invested millions of dollars into a company named Privoro, which has been working alongside the military on cell phone cases that keep out hackers—and allow officials to carry their devices into sensitive areas.

Privoro is just one of many defense investments Feinberg made in the private sector, giving him insight into virtually every hot-button topic in modern warfare: drones, satellites, hypersonic missiles, artificial intelligence. Private and patriotic, Feinberg bet on such businesses through his Wall Street firm, Cerberus Capital Management, and out of his own pocket. Feinberg also surrounded himself with ex-government officials, including George H. W. Bush’s vice president and Barack Obama’s acting CIA director.
…
Feinberg, positioned to run the day-to-day operations of the defense department while Hegseth serves as the face of the enterprise, is fully focused on an area that he knows cold.

The piece also discusses Feinberg’s Wall Street pedigree and associates:

einberg started his career on Wall Street and soon crossed paths with some of the most sophisticated—and controversial—financiers in America. He began at Drexel Burnham Lambert, working as a trader at the firm that eventually collapsed in a fraud scandal that sent billionaire Michael Milken to prison. Feinberg got out before the downfall, moving to Gruntal and Company, where he overlapped with Steven Cohen, whose later firm pleaded guilty to insider trading (costing Cohen $1.8 billion personally).

Avoiding those problems, Feinberg carved out a niche as a distressed investor, less politely referred to as a vulture, who knew how to find meat on the bones of decaying businesses. He left Gruntal in 1992 and started Cerberus, named after the three-headed dog that guards the gates of hell. Sometimes things got nasty. In the late 1990s, for example, Feinberg served on the board of a healthcare firm while holding a chunk of the company’s debt. After the directors negotiated with debtholders over a restructuring, an attorney working with the board said Feinberg recused himself during the discussions. But shareholders complained when a CEO that Feinberg recruited steered the business into bankruptcy, sparking suspicions that the debtholders were trying to improperly snatch the company. A bankruptcy court sided with Feinberg.

As his profile increased, Feinberg worked to remain in the shadows.

Let’s try and shine more light on Mr Feinberg as we go from here on.

And speaking of cockroaches who might have lost their knack for running when the kitchen lights come one, let’s not forget to smack these next ones with a rolled up newspaper.

Commerce Secretary Lutnick’s Family Trades Together

I’ve been remiss in leaving the antics of Trump 2.0 Commerce Secretary Howard Lutnick and his illustrious family out of these reports. Let’s end that here.

This November 20, New York Times report has been a burr under my saddle since it documents the Lutnick family’s doings in my native Texas panhandle.

Kyle Lutnick, the 29-year-old scion of his family’s real estate business, traveled in July to Amarillo, Texas, to walk a dusty tract of land with the head of an artificial intelligence start-up called Fermi America.

He was touring the site of a future data center with Toby Neugebauer, a billionaire who is building one of the behemoth facilities that will power the next generation of A.I. Mr. Lutnick’s company was helping raise capital for the center, banking millions in fees in the process.

“Polite young man,” Mr. Neugebauer said in an interview.

A month later, Kyle’s father, Howard Lutnick, was photographed with Mr. Neugebauer at an event near the White House that celebrated Fermi’s partnership with a South Korean company on the same data center project.

This sequence of events — a son making money on a project his father is boosting as a federal official — has come up repeatedly since President Trump tapped Howard Lutnick to head the Commerce Department, according to an investigation by The New York Times.

In that role, Mr. Lutnick has twisted the arms of American allies, dangling policy favors in exchange for investments in U.S. industrial projects. At times, these tactics have created opportunities for his family’s clients to gain access to much-needed foreign capital, The Times found.

The NYT goes on to try to put the Lutnick family’s portion of Trump insider deals into historical context saying, “never in modern U.S. history has the office intersected so broadly and deeply with the financial interests of the commerce secretary’s own family.”

And how:

Since February, Kyle Lutnick and his younger brother Brandon, 27, have helped run a network of companies under the corporate umbrella of Cantor Fitzgerald L.P. The companies, led by their father until this year, include the Wall Street investment firm Cantor, the securities brokerage BGC Group and the real estate company Newmark Group.

Brandon is the chairman of Cantor Fitzgerald L.P., and Kyle is the executive vice chairman. The sons and their two younger siblings have a controlling ownership stake in all three companies in the network.

The family’s companies operate in a wide range of industries, from cryptocurrencies to data centers, that overlap with Mr. Lutnick’s work in government

The Times is the latest to flag the Lutnick Familys’ doings as problematic. The Real Deal warned of nepotism when the deals were announced earlier this year and raised questions about Lutnick’s role in the companies he “handed off” to his sons while he serves the public:

Howard Lutnick raised eyebrows last week when he named his 28- and 27-year old sons to key leadership positions at Newmark and Cantor Fitzgerald.

It’s fair to question what kind of expert guidance a pair of 20-somethings can offer seasoned CRE veterans who have been in the business since before the Lutnick sons were even born.

But by also elevating Barry Gosin and Nemark’s top legal officer, Lutnick moved to continue the status quo as much as he could — even if the company would benefit from a more significant shakeup.

“No one’s under any delusion that somehow he’s not there anymore,” said Piper Sandler analyst Alex Goldfarb.

Newmark’s stock price pretty much shrugged off the news last week that Brandon Lutnick, 27, had been appointed chairman of Cantor Fitzgerald and Kyle Lutnick, 28, named executive vice chairman of the company as their father was confirmed as Donald Trump’s Commerce secretary. Kyle was also named to Newmark’s board of directors.

Their inexperience and the nepotism at play left many with the impression that they’d have less of a hand in the companies than their father.

“They’re kids,” one person familiar with the Lutnicks said. “There’s no more or no less than what you see.”

Good to know that Daddy Lutnick is only a phone call or text away from his boys. Wouldn’t want those nepobabies falling off the cabbage truck into a big pile of money and hurting something.

With the latest special election results adding strongly to the narrative that Trump’s GOP is due for a drubbing in the 2026 midterm elections, the Trump tariffs failing to stop the relentless contraction of the American manufacturing sector, the MSM increasingly willing to admit the Ukraine war is a disaster, and Secretary Hegseth flailing to avoid wearing the war criminal jacket, there’s no reason to believe Team Trump will turn things around anytime soon.

That’s bad news for those who’ve been feasting at the trough via Trump insider deals.