Thomas Friedman calls Craig Mundie his “technology tutor.” He’s said it publicly, repeatedly, for over a decade. Perhaps it’s meant to sound endearing. It’s actually a sad confession. The most influential foreign affairs columnist in America openly outsources his entire understanding of technology to a single person. Why?

That person’s track record deserves closer examination within context of a larger institutional failure rated as success.

Microsoft Failure Man

In 1982, Mundie co-founded Alliant Computer Systems, a maker of vector-parallel mini-supercomputers. He became CEO. The company filed for bankruptcy June 5, 1992 because they didn’t see the PC coming.

He joined Microsoft that same year to run the Consumer Platforms Division. Here is what he built and championed:

Year	Product / Initiative	Outcome
1992	Windows CE	Dead
1990s	Pocket PC	Dead
1990s	Auto PC	Dead
1997	WebTV Networks ($425M acquisition)	Dead
1990s	Interactive television	Dead
2000s	Digital rights management strategy	Dead

When Bill Gates stepped back from daily operations in 2006, Mundie and Ray Ozzie were appointed to fill his visionary role. Mundie became Chief Research and Strategy Officer. During his tenure in that position, Google beat Microsoft to self-driving cars. Apple beat Microsoft to voice recognition with Siri. Microsoft missed mobile. Missed search. Missed social. Missed cloud computing until Satya Nadella arrived and reoriented the entire company away from the strategy Mundie had been overseeing.

To be fair, Ballmer overruled strategy recommendations, and search and social blinders may have been other divisions’ calls. But show me the wins. By late 2012, Mundie was moved to “Senior Advisor to the CEO,” the corporate equivalent of a quiet pasture upstate where his opinions wouldn’t be heard anymore. He retired in 2014.

Selling Invisible Pants to Elites

What happens to a technology executive whose products all failed but whose rolodex thrived? He becomes a bogus sage. Mundie landed on the National Security Telecommunications Advisory Committee under three presidents. Obama’s PCAST council. The Bilderberg Group steering committee, which he attended every year from 2003 to 2019 except one. The World Economic Forum. And then the capstone: co-authoring Genesis with Henry Kissinger and Eric Schmidt, a book about AI published in November 2024.

Kissinger.

The architect of the secret bombing of Cambodia. The man who backed the coup in Chile and the Indonesian invasion of East Timor. Who enabled the Pakistani genocide in Bangladesh. Who treated civilian populations as abstractions to be managed through force. This is who Mundie chose as his co-author on the governance of a technology that will reshape civilian life everywhere.

That tone-deaf choice tells you everything about the Mundie gambit: power managed by the powerful, consequences borne by everyone else. Talk down and ignore reality.

The technology product arc of disasters was foreshadowing. Build things that fail. Accumulate institutional access along the way. Pivot from practitioner to advisor once the failure pattern becomes undeniable. The access persists because Davos doesn’t audit skills like product launches. It rewards gravitas in presence.

The Column

This week Friedman published a column about Anthropic’s Claude Mythos announcement. His source for interpreting its significance was, naturally, Craig Mundie. The column treats Mundie’s analysis as authoritative. It contains Mundie’s three-step framework for responding to the threat. It quotes Mundie at length. It cites no other technical source.

Friedman writes:

[Mundie is] a former director of research and strategy at Microsoft, a member of President Barack Obama’s President’s Council of Advisors on Science and Technology and an author, with Henry Kissinger and Eric Schmidt, of a book on A.I. called Genesis.

Every word of that sentence is true. Every word of it is also designed to obscure the fact that Mundie’s actual technology career was a sequence of expensive bets that all lost.

The credential list substitutes for any actual performance record.

The Friedman column is similarly bad at placing bets. It describes AI-powered vulnerability discovery as if no one had ever heard of fuzzing, static analysis, or red team operations.

OMFG.

He illustrates the threat with a scenario where children accidentally take down a power grid. This is the Computer Fraud and Abuse Act (CFAA) debate of 1984, recycled. Congress passed it in 1986 after WarGames convinced legislators that teenagers with modems could launch nuclear weapons. Before that, Captain Crunch and the phone phreakers were going to launch nukes, shut down power or destroy the telephone system.

Did he just wake up from 1986?

By early 1999 I personally had reported clear text authentication on the American bulk power grid in five states. Thousands of routers vulnerable to trivial destruction. Did I break anything? The old geezer in a suit panicking that “kids will break everything” has been the go-to move for people who want to centralize control of new technology for forty years. Friedman presents it as an original insight, as if nobody remembers the 414s.

He proposes US-China cooperation on AI governance in the same week the US is actively restricting chip exports to China to prevent exactly the AI capability development he’s now asking them to collaborate on. He doesn’t notice this dumb contradiction because he’s transcribing, not analyzing. He would do far better to trust AI than the hallucinations of Mundie.

Meatspace

A columnist who calls someone his “tutor” on a subject is telling you he cannot independently evaluate what that person says. Friedman admits no second opinion on technology, and he lacks the technical literacy to know what questions would surface one. Mundie tells him this is unprecedented. Friedman writes that it’s unprecedented. Mundie says it requires US-China cooperation. Friedman writes that it requires US-China cooperation.

This is how a man who got WebTV, Windows CE, the Pocket PC, interactive television, and digital rights management wrong becomes the person explaining artificial intelligence threats to New York Times readers.

The technology tutor model has an obvious flaw. The student can’t evaluate the false tutor, because the student can’t evaluate the subject. He can only evaluate the tutor’s confidence, which is deeply ironic. Just like the real danger with a bad AI chatbot, confidence is the one thing Craig Mundie has never lacked.

The threat of AI is the relationship Friedman has with Mundie, not the AI.

Trump bankruptcy is on the horizon again, this time on the ocean. Trump Steaks, Trump Vodka, Trump University, Trump Airline and now… Trump Oil.

Court filings tell the story. Trump applying the American military, like the mob flexes protection racket muscle, to monopolize a market isn’t what he thought it would be. Trump is spending tens of millions of taxpayer money grabbing and maintaining aging ocean tanker rust buckets that he can’t sell, holding oil he can’t offload, and continuing the program anyway into an expanding disaster.

Here’s a table for every tanker seized so far under his ill-considered “Operation Southern Spear”.

The Trump Junk Fleet

Tanker	Seized	Cargo (barrels)	Est. Cargo Value	Vessel Value	Known Cost to U.S.	Status
Skipper	Dec 10, 2025	1.8M	$120–$135M	~$10M	$47M + $450K/mo + $5M pending	Held; DOJ asking court to sell
Centuries	Dec 20, 2025	~2M	~$130M	Unknown	Unknown (moored at Galveston)	Held
Bella 1 / Marinera	Jan 7, 2026	Empty	$0	Unknown	Atlantic chase + ongoing	Held; pure cost center
Sophia	Jan 7, 2026	~2M	~$130M	Unknown	Seizure costs; cargo returned	Returned to Venezuela
Olina	Jan 9, 2026	Loaded	Unknown	Unknown	Seizure costs; cargo returned	Returned to Venezuela
Veronica	Jan 15, 2026	Empty	$0	Unknown	Unknown (moored off Puerto Rico)	Held; pure cost center
Sagitta	Jan 21, 2026	Unknown	Unknown	Unknown	Unknown	Held
Aquila II	Feb 9, 2026	~700K	~$45M	Unknown	15,000 km pursuit + ongoing	Held; not formally seized
2 additional (unidentified)	Unknown	Unknown	Unknown	Unknown	Unknown	Held per NYT

That’s just eight confirmed seizures already painting the obvious picture.

The NYT reports ten total with Venezuelan ties. Two (Bella 1 and Veronica) were empty when seized. Two more (Sophia and Olina) were returned to Venezuela. The U.S. absorbed the full operational cost of every seizure and got nothing back on four of them.

The Asset Trap

A tanker is not a seized bank account. It’s not a pile of gold. It is like a slumlord grabbing a condemned property, a decaying organism that consumes capital every second it sits unrepaired. Taking the decrepit hulls means the U.S. government has made itself into the world’s most expensive and insolvent shipping company.

For what?

The Skipper’s court filings are Trump Steaks all over again.

The U.S. government was forced to spend $47 million in three months on repairing and maintaining a vessel worth $10 million. Instead of all the things $47 million could have done domestically, it’s tangled up in acquired foreign debt.

Read that Trump businessman genius move again.

He’s blowing 4.7x a ship’s value just to keep it afloat in Texas. Oil storage runs $15,000 a day. Another $5 million is pending for insurance and crew. The DOJ’s own asset manager wrote that these costs “far outstrip standard assets.”

Grade school children understand the math showing this is bad, but not Trump. Previous American procedure was to seize the assets (oil) at sea with a siphon and let the liability (ships) sail on. Makes sense, right? The Trump model has been to take all the liability, immediately undermining the assets.

The Storage Bottleneck

Trump’s army of sycophants can’t simply sell the oil, deteriorating on old ships. These are civil forfeiture cases tied up in U.S. District Court in Washington. The Skipper’s cargo — worth $120 to $135 million — has been sitting unsold since December. At $450,000 a month in storage alone, a 12-month legal process would burn up $5.4 million before a buyer is found. Add the $47 million in catch-up maintenance and $5 million in pending costs, and nearly half the cargo value evaporates before a single barrel is sold.

The DOJ is now asking the court to allow an emergency sale of the Skipper’s oil before the massive losses become obvious to the public. That’s the Trump circus creating emergencies by admitting their strategy is hemorrhaging money faster than they can bully people into covering it up.

Net Recovery Projection

Only the Skipper has detailed cost data. But the Skipper is the template. These are all aging, end-of-life shadow fleet tankers that were past commercial retirement when they were seized. If the Skipper’s costs are even roughly representative, here’s what the full fleet of eight held tankers looks like over time.

Assumptions: maximum recoverable cargo across the fleet estimated at $500 million. Initial repair costs averaged at $20M per tanker (conservative — the Skipper hit $47M). Ongoing monthly costs per tanker estimated at $2–3.5M (maintenance, crew, insurance, storage). Neither scenario includes military operational costs, legal fees, or cargo depreciation.

Scenario	Initial Repair (fleet)	Monthly Burn (fleet)	Total Cost at 6 Mo.	Total Cost at 12 Mo.	Max Recoverable Cargo	Net at 12 Mo.
Conservative ($20M avg repair, $2M/mo per tanker)	$160M	$16M/mo	$256M	$352M	~$500M	+$148M
Skipper Rate ($40M avg repair, $3.5M/mo per tanker)	$320M	$28M/mo	$488M	$656M	~$500M	–$156M

Under the conservative scenario — which assumes each tanker costs less than half what the Skipper actually cost — the operation barely breaks even at 12 months. Under the Skipper rate, the operation goes underwater at roughly month 6 and never recovers. By month 12, the U.S. has spent $156 million more than the oil is worth.

Month six!

The Risk Nobody’s Pricing: Environmental Liability

Everything above is the optimistic scenario. It assumes nothing goes wrong with the ships themselves. That assumption deserves scrutiny.

These are single-hull, end-of-life “ghost fleet” tankers. They were built over two decades ago. They have been running intentionally dark, spoofing locations, skipping important inspections, and operating without valid safety certifications for years. So Trump has targeted absolute worst junk assets, with the least chance of positive return, for seizure.

Several were already rusting through, for obvious reasons. The Skipper’s $47 million in immediate repairs were totally avoidable by not seizing it.

I suspect the people who never maintain anything and have no concept of safety are the ones assuming all ships are equally valued.

Seizing unfit vessels on the verge of disaster actually makes the U.S. government the “responsible party” under the Oil Pollution Act of 1990. OPA 90 imposes strict liability on the owner or operator of any vessel from which oil is discharged into U.S. waters.

Bush signed OPA 90 in response to the Exxon Valdez disaster. But as the Netflix documentary The White House Effect now documents using his own presidential library memos, his chief of staff John Sununu was simultaneously running a back channel with Exxon to neutralize every environmental commitment the administration made.

Perhaps that’s the Trump plan too.

The filmmakers found never-before-seen correspondence between oil executives and the White House chief of staff — memos in which, according to director Jon Shenk, Sununu openly bullied the President. EPA chief Bill Reilly told the filmmakers that even he was shocked by the tone.

The oil industry’s reaction to the Valdez spill was not remorse. It was to circle the wagons — applying the tobacco industry playbook of deny, counter, and split the electorate. Exxon wrote directly to Sununu as their line into the government. He convened a confidential “Global Warming Scientific ‘Skeptics’ Meeting” stacked with climate contrarians funded by coal companies. And the Bush White House forced NASA scientist James Hansen to alter his own congressional testimony to downplay climate risks.

The law survived the Bush corruption that is responsible for growing climate change disasters we experience today. The intentions behind it didn’t, perhaps by design. And now that same OPA 90 framework — strict liability, uncapped when safety regulations are violated — is the one that’s governing Trump’s seized tanker fleet. What are the chances it holds?

“Strict” means no-fault, so if the oil spills, the responsible party pays. And the current OPA liability cap for a single-hull tank vessel over 3,000 gross tons is the greater of $4,000 per gross ton or $29.6 million. But the cap vanishes entirely if the spill resulted from “violation of an applicable Federal safety, construction, or operating regulation.” These ships have no valid classification, no current safety certificates, and no double hulls. The cap would not survive a normal courtroom.

Here is what the uncapped liability looks like.

Spill Scenario	Volume	Historical Comparable	Cleanup Cost Range	Total Liability (incl. damages)
Minor hull breach (1 tanker, partial cargo)	~500K barrels	Larger than Exxon Valdez (262K bbl)	$2–4 billion	$3–7 billion
Major structural failure (1 full tanker)	~1.8M barrels	Approaching Deepwater Horizon scale	$5–15 billion	$10–25 billion
Cascading failure (2+ tankers at anchorage)	3–4M barrels	No historical precedent	$15–40 billion	$25–65 billion

The numbers have precedent. Exxon spent roughly $2.5 billion on cleanup alone for 262,000 barrels — about $9,500 per barrel spilled. BP’s total Deepwater Horizon liability exceeded $20.8 billion in settlements, with total costs above $65 billion. The Skipper is sitting in the Galveston Offshore Lightering Area with 1.8 million barrels of heavy Venezuelan crude — nearly seven times the volume of the Exxon Valdez spill — in a hull that required extensive repairs so it wouldn’t wreck Texas.

And the government plans to add even more debt from captured Iranian tankers to this fleet. Iranian shadow fleet vessels are notoriously among the worst-maintained ships afloat. By seizing them, the U.S. takes the environmental and safety liability another step deeper. One major hull breach in a U.S. port turns a hundred-million-dollar waste into a multi-billion-dollar ecological disaster. Talk about sunk cost.

The Ledger

Trump is pushing deranged reports of gross cargo value, to generate $130 million headline figures, as money he magically made. That’s clearly not how anything works. The actual balance sheet looks very different.

Line Item	Headline Number	Actual Number
Gross cargo value (all held tankers)	~$500M	~$500M (if every barrel is eventually sold)
Emergency repairs (fleet)	Not reported	$160–$320M (based on Skipper rate)
Ongoing maintenance, crew, insurance	Not reported	$16–$28M per month, compounding
Oil storage	Not reported	~$3.6M per month (est. across loaded tankers)
Military operations (carrier groups, SEALs, 160th SOAR, CG cutters)	Not reported	Classified / buried in defense budget
Legal fees and court costs	Not reported	Unknown; 10 separate forfeiture cases
Empty tankers (Bella 1, Veronica)	“Seized!”	Pure liability; $0 revenue
Returned tankers (Sophia, Olina)	“Seized!”	Sunk cost; $0 revenue
Environmental tail risk (OPA 90)	Not mentioned	$3–65 billion per incident, uncapped
Net position at 12 months	“Financial boon”	+$148M (best case) to –$156M (Skipper rate)
Net position if one hull fails		–$3 billion to –$65 billion

Every day Trump’s seized liabilities sit in U.S. waters, the gap between artificially gross headlines and the balanced reality ledger widens.

The one number that should keep the DOJ’s asset manager awake at night is the OPA 90 tail risk of a single-hull structural failure in a Texas anchorage, which doesn’t appear in any press conference. Bush signed that law. Sununu gutted the intent. And now Trump is parking the exact category of vessel it was designed to eliminate — single-hull, uncertified, end-of-life tankers loaded with heavy crude — in American waters, on the American taxpayer’s tab, with the American coastline as collateral.

This is what Trump Oil looks like, just like every other Trump bankruptcy, as court filings reveal the disinformation behind his toxic press releases.