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Kai Bird

Kai Bird

American author and columnist

Sep 18, 2026

9:04
not admitting any problems at all like we expected the high price of oil uh the other day he was asked by a reporter do you have any regrets about the iran war and he said none i guess that's true to form and and tell me kybert he learned some of it from roy cone
9:19
he learned all of it from roy cone Roy was, as the title says, he was a scoundrel, a villain, but a very charming villain.
9:29
He could be over the dinner table, a great gossip.
9:33
He was raised by his mother, Dora, in the Bronx and in New York City and the Upper East Side.
9:40
She raised him with no guardrails.
9:44
She told him, you know, the rules are for little people and you're special, Roy.
9:50
So he took this to heart.

5 MINS LATER

14:56
That fits into the early Trump in New York, under the tutelage of Roy Coe? Oh, absolutely.
17:44
Yeah, yeah
17:44
...
17:44
in housing in Queens, in their apartments owned by the Trump Organization, and it was very blatant.
17:50
It was an open-and-shut case.
17:52
And of course, Roy famously said, "Oh, you should fight it." You know, "You should sue the, the feds.
17:58
Let's hold a press conference and announce a $100 million defamation suit against the federal government." You know, it was a nonsense suit, and it was dismissed within two months.
18:08
But, uh, Trump loved this, and Roy was, um, sort of a, a social racist.

6 MINS LATER

24:10
How did the relationship between, uh, Donald Trump and Roy Cohn change as Trump became more famous and more powerful?
5:36
But the new McCarthyism of the Trump era has many more victims.
5:40
Oh, it's much worse.
5:41
You know, when I started out as a historian and biographer almost 40 years ago now, I decided I wanted to figure out how power works in America.
5:51
So I started writing about establishment figures, John McCloy, the powerful Wall Street lawyer, Mac Bundy, the Harvard dean and national security advisor to Kennedy and Johnson, Robert Oppenheimer, the atomic physicist.
6:08
And I thought that that would be helpful for explaining how power works in a complicated democracy like this.
6:17
Now, in all of those books, I wrote a little bit about Roy Cohn, a sort of festering, nasty little lawyer who caused problems.
6:27
But he appears in those books as sort of inconsequential, historically speaking.

10 MINS LATER

16:13
They wanted to be seen with
35:47
He's not in that ilk at all.
35:49
No. He's, he's a villain, and he was raised to break all the rules.
35:57
And but that's what makes him interesting.
35:59
You know, H.L. Mencken used to say, uh, "What a dull world this place would be for ho- us honest men if it weren't for the sinners."
38:50
From Queens, right
38:51
And Roy Cohn was a seasoned 40-year-old, uh, lawyer who, who knew everyone and was a lawyer to all five mob families in New York City.
39:02
And he, he was a famous guy, and he, he helped Donald Trump get the tax abatements he needed for the first big deal, the, uh, renovation of the Commodore and then the building of Trump Tower, uh, which was all, w- which was built with concrete.
39:19
Well, Roy Cohn was the lawyer to Fat Tony Salerno, who controlled the concrete business and the unions that poured the concrete, and Donald Trump needed the-
31:03
Interesting lessons he imparted upon
31:05
his protege.
31:06
Oh, he would celebrate it.
31:08
He predicted to Donald Trump.
31:10
He said, someday, if you want, you could be president.
31:15
He molded this young man when he first met him at the age of 27.
31:19
And he thought that Donald was...
32:20
Is it the environment that we are currently living in, the ability for misinformation and disinformation to spread as quickly? Conspiracy theories being a cottage industry for a lot of people, especially online, that makes this era worse than when Joel McCarthy was there?
2:27
Tell us about how he was the prosecutor who sent a couple, Julius and Ethel Rosenberg, to the electric chair.
2:36
Yes, Roy was, Roy Cohn was only, uh, right out of law school.
2:40
He was in his early 20s, and he became an assistant prosecutor on this famous Rosenberg atomic spy case, and he was relentless.
2:50
And he, he was the kind of l- lawyer who always broke the rules.
2:56
So, uh, during the Rosenberg case, he had ex parte conversations with Judge Irving Kaufman, who was pr- the presiding judge.
3:05
And Roy just, you know, uh, he, [clears throat] he guided the judge and, uh, was relentless in, in bringing a prosecution and, and persuading the judge to inflict the death penalty, sending not only Julius, but also Ethel, the do- the mother of two young boys, to the electric chair.
3:29
And that wa- that gave his first sort of, that, his first sort of public renown was coming from that Rosenberg case.

8 MINS LATER

11:50
... regardless of the position that they have, always used the legal approach as a weapon, always accuse the accuser?
25:26
So is this an example of the legacy of Roy Cohn, Kai?
25:32
Oh, absolutely.
25:32
You know, I don't think you can understand the last 10 years of the Trump era unless you understand Roy Cohn's life.
25:42
The biographers of Trump, he's a slippery subject for any biographer.
25:54
He's too ephemeral.
25:57
You can't trust what Trump says.
26:00
His stories are too slippery.

16 MINS LATER

41:40
Is that apocryphal?
Jeffrey Brown
Jeffrey BrownCORRESPONDENT
33:17
What jumped out at you? What stood out, uh, especially vis-a-vis Roy Cohn's involvement?
33:24
Roy was a gay, closeted man then, but he went after gay civil servants in the State Department r- ruthlessly.
33:35
Uh, he knew exactly what he was doing.
33:38
He had this private life, and yet he was, uh, shamelessly going after fellow gays.
33:45
Um, that was shocking.
Jeffrey Brown
Jeffrey BrownCORRESPONDENT
36:27
But his most enduring afterlife, says Kai Bird...
36:30
But it's his values, his, uh, resentment of the establishment, uh, that now prevails in our politics.
36:41
He is the architect of this politics of resentment, resentment against the establishment of the elites, this sort of right-wing populism, this suspicion of immigrants.
Jeffrey Brown
Jeffrey BrownCORRESPONDENT
3:09
I quote in the book H.L. Mencken's
3:12
observation that the world would be a very dull place for us honest men if it were not for the sinners.
3:22
And that's Roy Cohn.
3:23
He was fascinating.
3:25
He was charming over the dinner table.
3:29
But he was transactional.
3:32
He knew how to make things happen.
Jeffrey Brown
Jeffrey BrownCORRESPONDENT
3:58
Trump
Jeffrey Brown
Jeffrey BrownCORRESPONDENT
3:09
I quote in the book H.L. Mencken's
3:12
observation that the world would be a very dull place for us honest men if it were not for the sinners.
3:22
And that's Roy Cohn.
3:23
He was fascinating.
3:25
He was charming over the dinner table.
3:29
But he was transactional.
3:32
He knew how to make things happen.
Jeffrey Brown
Jeffrey BrownCORRESPONDENT
3:58
Trump
12:39
Now, who were the Bundy brothers?
12:41
They were sort of the next generation of the establishment that McCloy represented.
12:47
McCloy had worked with their father, Harvey Bundy, in the War Department.
12:51
Harvey Bundy was a top assistant to Henry Stimson, the war secretary.
12:57
McCloy was the assistant secretary.
12:59
And so McCloy, during World War II, knew the young Bundy brothers.
13:06
And they were brilliant sort of second generation establishment Boston Brahmins.

25 MINS LATER

38:13
Schein.
12:06
Now, who were the Bundy brothers?
12:09
They were sort of the next generation of the establishment that McCloy represented.
12:15
McCloy had worked with their father, Harvey Bundy, in the War Department.
12:19
Harvey Bundy was a top assistant to Henry Stimson, the war secretary.
12:25
McCloy was the assistant secretary.
12:27
And so McCloy, during World War II, knew the young Bundy brothers.
12:34
And they were brilliant sort of second generation establishment Boston Brahmins.

23 MINS LATER

35:42
Can you explain what that was all about?
7:43
Does Roy learn how to drag it out for a long time?
7:45
Yeah, he dragged it out for two years.
7:47
He... got every possible delay.
7:53
At one point, in court, he accuses a deputy prosecutor named Donna Goldstein of fraud, legal fraud.
8:07
He claims that she was calling up Trump organization employees and tenants in the Trump apartments in Queens and threatening them if they didn't testify against Trump.
8:28
And of course, this was a completely made up story.
8:32
But the judge had to take it seriously and halted the proceedings for two weeks and then reconvened.

29 MINS LATER

37:51
It's an
8:20
Arthur Schlesinger was not lying to us when he said the cycles of American history are doing their thing.
8:27
Yes, absolutely.
8:28
You know, when I started out becoming, teaching myself to become a historian, on my first biography of John McCloy, I had to write about the McCarthy era and Roy Cohn, and I regarded it as sort of a defining low point in the American story.
8:51
something that we had recovered from, something, you know, the witch hunts had been defeated.
8:58
And, you know, I was naive.
9:02
Now I've reconsidered.
9:03
And, you know, what happened in McCarthyism was a recurring thing.

35 MINS LATER

44:00
I mean, how did this keep, how did it just keep going?
42:36
I gave folks a little bit of it
42:37
itWell, it was their first encounter and, uh, it, it- you know, Donald Trump at tw- age 27 really liked this advice.
42:47
Uh, you know, he w- Roy was teaching him that he, he should flout the rules, ignore the federal judiciary, and, uh, just declare victory in a public forum.
43:03
So, you know, what was most important to Roy was just the, the public fight, and his rule was always deny, deny, deny, never apologize, and attack, attack, attack.
43:15
And, you know, he, he had an opportunity for 13 years as Donald Trump's main lawyer to sort of mold this young man-
43:41
Um, you quote a New York Times reporter in the 1970s who said, and this is gets to what you were just talking about, "Roy Cohn worked with a three-dimensional strategy, which was one: Never settle, never surrender; two: Counterattack, countersue immediately; three: No matter what happens, no matter how deeply into the muck you get, claim victory and never admit defeat." Thu- th- those would appear to be the exact lessons that Trump is employing now, aren't they?
44:12
Exactly.
44:12
Same le- lessons.
10:22
What happened to him? Did he go into sort of self-imposed exile? How long between that and meeting Donald Trump?
10:29
Well, you'd think he'd go hide, go into exile, as you say, but no, that's not what happened.
10:37
You know, he left Washington when he was fired as chief counsel in the wake of the Army McCarthy televised hearings, which were very controversial, and he was perceived as a scoundrel on national television, seen by 20 million people.
10:56
He's fired, but he comes back here to New York.
10:59
And that very month, he's fetid and celebrated at a dinner at the Hotel Astor in Times Square.
11:07
And he makes his way in New York society initially as a high-priced divorce lawyer.
11:15
for the rich and the famous.
13:02
And obviously, it's important now for me to ask you, what was the meeting between Roy Cohn and Donald Trump and the case that bound them together when Trump was still a developer?
35:53
What did he see in a young Donald Trump that made him think he could shake this person?
35:59
Well, that's a good question.
36:00
They met in October of 73 at Le Club, a private dining establishment here in midtown Manhattan.
36:10
Trump went over, the young 27-year-old Trump went over to Roy Cohn and introduced himself.
36:15
He recognized Roy as the mob lawyer.
36:18
And Trump was involved in a lawsuit at that point.
36:24
He was being sued by the feds for racial discrimination in the Trump organization's apartments in Queens.
38:07
And he taught those lessons that Trump seems to have learned really, really well.
37:23
What does it tell you that that's still what Trump thought then?
37:28
Well, I think Roy Cohn was one of Donald Trump's only true friends.
37:35
uh quite literally uh you know one of the sources for our book which it goes in is deeply biographical one of the sources is peter mantiso the late journalist who sat roy cone down for uh months at a time for hours and hours of interviews and we obtained from his widow the a thousand pages of transcripts of these interviews and uh peter manso says that when Roy Cohn died in August of 86.
38:05
There was memorial service a few months later in Manhattan.
38:10
And Trump, not surprisingly, showed up.
38:13
He stood in the back.
38:15
And Manso, Peter Manso, observed him weeping.
39:54
You seem to think people like Oppenheimer, Cohn, obviously what Trump became, shapes our world.
13:09
Now, this story was initially told
13:13
back in 1993 by the Irish journalist Anthony Summers in a biography of J. Edgar Hoover.
13:23
And it's a really pretty good book.
13:26
And Summers is a good journalist, but it was greeted with incredulity.
13:34
The reviewers critics of the FBI said, no, this is not believable.
13:43
J. Edgar Hoover would never have put himself in such a position.
13:50
But we got new evidence.

26 MINS LATER

39:50
But there is this other young man who happens to be there.
27:48
But the legacy that he left is really America today and Trump today because for anyone who's seen The Apprentice, you know, the film, Trump is the apprentice to Roy Cohn's school of political thought, right? Or maybe we should just say political bullying.
28:06
Yes.
28:07
Well, Roy Cohn was the mentor for Donald Trump.
28:10
They met in October of 1973.
28:13
But by then, you know, Roy was an, a man, a powerful lawyer fixer in his, i- i- in his 40s.
28:20
Donald Trump was 27.
28:23
And, uh, Roy Cohn had come on the American political landscape in 1952, '53 as one of the prosecutors of the Rosenberg atomic spy case, famous, uh, uh, spy case in America.

6 MINS LATER

34:35
It was just bullying either side of the law, wasn't it? I mean, do you think, do you think he was actually a talented lawyer?
40:46
I gave folks a little bit of it.
40:48
Well, it was their first encounter.
40:50
And, you know, Donald Trump at age 27 really liked this advice.
40:58
You know, Roy was teaching him that he should flout the rules, ignore the federal rules.
41:07
judiciary, and just declare victory in a public forum.
41:13
So what was most important to Roy was just the public fight.
41:18
And his rule was always deny, deny, deny, never apologize, and attack, attack, attack.
42:22
Same
26:06
What did they see in each other? Because you seem to see Trump as a person who wishes he was, you know, tall, good looking, blonde, moneyed, not Jewish, you know, the power guy of New York that he was too small, ugly and an outsider to be.
26:20
Right.
26:21
Well, it was a mutual beneficial partnership, right? Roy saw this up-and-coming young entrepreneur who had big ambitions for real estate in Manhattan.
26:33
And Roy could open the doors for him, and he could get him the zoning permits he needed.
26:38
And he came very close to him.
26:42
I mean, he was responsible for the Trump Tower zoning permits that allowed Trump to build this landmark in midtown Manhattan.
26:51
And they became so close that they were on the phone, you know, a dozen times a day.
30:01
Do you feel differently about that generation of people now that we're kind of, the whole world is living under a man who lives by Roy Cohn's values and by that kind of Studio 54 ethic that nothing matters but the velvet rope, nothing matters but the beautiful people, rules are for the losers, rules are for the little people?
33:34
But he was always claiming he didn't have any money.
33:36
He was into all sorts of nefarious business practices.
33:39
And he would, you know, take on famous clients like Ronald Perlman, the cosmetic... entrepreneur.
33:47
In his first divorce case, he hired Roy Cohn at the suggestion of Andrew Stein, the Manhattan borough president.
33:55
outrageous story, but typical of Roy.
33:58
They go into court on the big day, and Roy walks in alone with his client, Ron Perlman.
34:06
No papers, no assistance.

17 MINS LATER

50:58
As an attorney, he could be pretty sloppy.
6:37
But where does he come from? What are his roots?
6:40
He's from the Bronx.
6:42
He's very much a creature of New York.
6:43
His father was a Bronx, New York State judge.
6:48
His family was Jewish, Democratic, liberal people.
6:54
And yet young Roy grew up with a resentment of the New York establishment.
7:02
I try not to psychobabble in biography, but you do have to understand his childhood.

20 MINS LATER

26:40
And how did you find Kerr? And what made you believe that this was a story that you could use in your book? Because you have a very high standard of evidence.
39:17
Why? What did he say and what do you think is real?
39:20
Well, he claims that two FBI agents gave him a briefing on how Alger Hiss and many other liberal Democrats associated with Dean Acheson were actually secret communists and had infiltrated the State Department.
39:34
Do you believe that? No, I think that was bullshit.
39:37
I think what happened was when Roy Cohn was 8, 9, 10 years old, his mother Dora, who was an enabling mother, she raised Roy with no guardrails, she was taking him up to Singh Prison every weekend to visit his beloved Uncle Bernie, who was the only banker who was imprisoned for bank fraud coming out of the 1929 crash.
40:02
Wow.
40:05
And Dora, the mother, told Roy that poor Uncle Bernie was a victim of a conspiracy of Jewish communists.
40:14
Right.
41:22
This was actually after my grandfather had been out of jail.

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