#1 The Mark: The KGB Had a Checklist for Picking Targets and Trump Checked Every Box

In the intelligence world, they call it a “mark.” The person who doesn’t know they’re being played. The one who thinks every good thing happening to them is because they deserve it - because they’re smart, because they’re special, because they’re a genius dealmaker with great instincts. The mark never sees the checklist. The mark never knows about the file.

This essay is about how Donald Trump became the mark.

In the introduction to this series, I laid out the KGB’s recruitment handbook - the literal checklist Soviet intelligence used to identify targets. “Pride, arrogance, egoism, ambition or vanity.” Financial corruption. Likelihood of gaining political power. [1][2] I also showed you how Czechoslovakia’s secret police started watching Trump in 1977, the year he married Ivana. [3][4]

But knowing the checklist existed and knowing WHO checked every box are two different things. The introduction was the what. This is the who and the how.

So let’s talk about Roy Cohn.

If you’ve seen The Apprentice with Jeremy Strong, you know the vibe, but the real version was worse. Cohn was the former chief counsel to Joseph McCarthy during the Red Scare. Helped prosecute the Rosenbergs. Then he moved to New York and became the go-to attorney for the actual Mafia. He represented Fat Tony Salerno, boss of the Genovese crime family. He represented Paul Castellano, boss of the Gambinos. He got disbarred in 1986 - partly for trying to defraud a dying client with a forced change to his will - and died five weeks later. [6]

This is the guy who taught Donald Trump how to do business.

And one of the first lessons was: the mob is your friend. Trump’s first big project was converting the old Commodore Hotel next to Grand Central into the Grand Hyatt. He was 29. He needed an unprecedented 40-year tax break from the city to make it work - the first one anyone asked for under a brand-new city program. The Trumps had given lavishly to Mayor Abe Beame, and according to Trump biographer Wayne Barrett, Beame said, “Anything they want, they get.” That single tax break cost New York City more than $410 million before it ran out in 2020. [7]

Then came Trump Tower.

The concrete?

Supplied by S&A Concrete - a company federal prosecutors charged Fat Tony Salerno with secretly controlling. [8][13] The mob poured the concrete for Donald Trump’s signature building. And according to the late reporter Wayne Barrett, Roy Cohn introduced Trump to Salerno at his townhouse - Trump denied it under oath. [8] This matters because it tells you who Trump was BEFORE the Russians showed up. By his early 30s, he’s a guy who gets sweetheart deals from politicians his family gave lavishly to, builds with mob concrete, and has a lawyer who represents the heads of two of the five families. He’s not a legitimate businessman who accidentally brushed up against organized crime. He’s a guy who can’t do business without it.

And this is exactly the kind of person the KGB’s checklist was designed to find.

Financial shadiness? He’s building with mob concrete and getting tax breaks through political donations. Compromising information in his background? He’s doing business with people who will eventually go to federal prison. Pride, arrogance, vanity? That’s literally the brand.

Likelihood of coming to power? Okay, that one seems like a stretch in 1984, right?

But the people watching him didn’t think so.

When Trump married Ivana Zelníčková in 1977, Czechoslovakia’s secret police - the StB - started watching the couple. That same year, an informant with the reported cover name “Lubos” began reporting on Trump’s company. [10] The files were stamped “top secret” and carried codenames like “Slusovice,” “America,” and “Capital.” [11] By 1979, they had ordered wiretaps on Ivana’s phone calls with her father, Miloš Zelníček, at least once a year. They intercepted their mail. They tracked who her family associated with in Czechoslovakia. They even monitored the Trump children’s visits to their grandfather. [10] Ivana’s father was registered as a “confidant” of the StB - Czech historian Tomas Vilimek told the German newspaper BILD that “the CSSR authorities forced him to talk to them because of his journeys to the US and his daughter. Otherwise, he would not have been allowed to fly.” [10]

The StB worked closely with the Soviet KGB - though nobody has shown how much of the Trump file made it to Moscow. [14] That’s how the pipeline could work - a Communist-allied intelligence service, hand in glove with Moscow, wiretapping an American businessman’s wife for over a decade.

And while the StB was wiretapping his wife’s phone calls, money with something to hide was already walking into Trump Tower. Almost the moment it opened, Haiti’s dictator bought a condo through a shell company, a Russian mob figure bought five, and a gambling kingpin brought a suitcase full of cash to his closing. Trump took the money. The full story of how that worked is the next essay.

But here’s what matters for this one: the StB was watching, and writing it all down.

And here’s what the file says by 1988.

In October 1988, a source with the cover name “Milos” - almost certainly Ivana’s father, given that his real name was Miloš - reported that Trump was being put under pressure to run for the US presidency. [10] The file says he was confident he would win - and that, at just 42, he planned to run as an independent in 1996. [9] This wasn’t gossip. This was a classified report in a file the StB had been keeping on the Trumps for over a decade. [9]

That’s not American media speculating. That’s a Soviet-allied intelligence service writing in an internal classified document, never meant to be public, that their surveillance target had been pressured to seek the presidency. In 1988.

And the Americans knew this kind of thing was happening. An unclassified CIA memo from 1988 titled “Soviet Efforts to Recruit American Citizens” warned that “American citizens are high priority targets for recruitment by the Soviet Union’s intelligence services,” and that “the Soviets are especially interested in Americans who occupy important positions in the fields of government, military service, business and finance, science and technology, industry, and academic research.” [12] Trump checked the business and finance boxes.

Here’s the thing that separates a mark from a target.

A target knows he’s in danger. A mark doesn’t.

The whole time, Trump thinks he’s winning. He thinks the money is coming to him because he’s a genius. Every time someone flatters him, every time they bring cash and don’t ask for receipts, every time they tell him he’s special - he thinks it’s because he IS special. He doesn’t see the checklist. He doesn’t know about the file with the code names. He doesn’t understand that every handshake is an audition and every “yes” is another line in a classified report.

By the late 1980s, the file was thick. The tests were passed. The mark was ready.

By then, he’d already been invited to Moscow, and he’d gone. That trip is essay 3. First, the money.

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Correction, October 12th, 2026: This essay first quoted Oleg Kalugin, the former head of KGB foreign counterintelligence, calling all this “typical” and saying Trump “may be useful” - the sources behind this essay don’t carry that quote, so it’s out. It said buyers poured into Trump Tower through anonymous shell companies with briefcases full of cash - Haiti’s dictator bought through a shell company, and a gambling kingpin brought a suitcase of cash to his closing. It said the StB shared everything with the KGB and sent what it learned to Moscow - the two worked closely, but nobody has shown how much of the Trump file reached Moscow. It said the StB opened a surveillance file on Trump in 1977 - it started watching the couple then, and its file was on Ivana. It said the 1988 report came from agents “Langr” and “Chod,” and that Trump decided he was too young to run and would try again in 1996 - the report came from a source called “Milos,” and it says he was confident he would win and planned to run as an independent in 1996. It said Roy Cohn was disbarred for stealing from a dying client - it was partly for trying to defraud one with a forced change to his will. It said Trump’s tax break was the first ever given to a commercial property in New York, that he got it because his father gave to the mayor, and that it’s still costing the city - it was the first asked for under a new city program, the mayor’s “Anything they want, they get” comes from biographer Wayne Barrett, and the break ran out in 2020. It said his family paid off politicians - they gave lavishly to the mayor. It said S&A Concrete was owned by Fat Tony Salerno and Paul Castellano and that Roy Cohn made the introduction - prosecutors charged Salerno with secretly controlling it, and the introduction is Barrett’s account, which Trump denied under oath. It said Trump checked every box on a CIA list of the Americans the Soviets wanted - he checked business and finance, not government or the military. And it said his Moscow invitation came after 1988 - it came in 1987.

Update, October 12th, 2026: A dead source link now works, another now points to the article that carries the 1988 report, the CIA memo links to its own page, and two sources were added at the end.