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Tim O'Brien

Tim O'Brien

American author

Oct 29, 2026

25:11
That's really all they've
25:12
got.
25:12
Well, I mean, you know, in Ohio, it's even worse than that, right? Obviously, you know, they're attacking her childhood and her own memories.
25:19
But I think that they're not arguing on policy.
25:22
They're not arguing about opportunity for voters.
25:25
They're like burglars testing the windows and doors of a house late at night.
25:29
They don't really they know they're not going to get arrested.

9 MINS LATER

34:19
What do you think?
6:56
We're probably going to see the same thing happening in Texas, probably going to see the same thing happening in South Carolina.
7:01
You know, Chris Quinn said a really, I think, simple, sophisticated and important thing, that they decided to write the editorial because this is not who they are.
7:11
He said, this is not who we are.
7:13
The Republicans have not asked themselves that question in more than a decade.
7:18
What they've been willing to do is trade their identity and whatever their classic conservative values were for Trump's stewardship.
7:26
And this ad and the decision to stick by it is just a distillation of grotesque incivility, horrendous judgment, and a willingness to sabotage people and their reputations in order to try to win because they're at a point right now in Ohio and nationally where they can't actually campaign on the merits.
7:46
You know, Ohioans are struggling with escalating healthcare costs.

31 MINS LATER

39:01
But I'm hoping Steve and their governors also communicate, because like I said, 80 percent's there.
36:13
Numbers like that feel like backlash to this larger pitch we've been seeing from the president.
36:19
And, you know, it's interesting because I think problems with the economy and problems with corruption had not stuck to Donald Trump during his first term.
36:29
And I think they're sticking now because Americans are struggling.
36:33
You know, they're seeing higher gas prices.
36:35
They're hit with higher electricity bills, food bills across the board.
36:39
They're facing uncertain futures.
36:40
It's embodied in the whole argument over data centers.

6 MINS LATER

43:03
Zelensky is in good company.
10:07
And if they can't or if their agendas won't work, they're going to pick up and leave, and this place will be left rumbled, scorched earth.
10:13
Well, what I would say about that era, you know, the 1890s, the Gilded Age, is I do think the titans of that era had a sense that they belonged to a community and they owed something back to that community.
10:24
They also profited massively off of that community.
10:28
But I think that in both of their cases, they also felt government got in the way.
10:34
And they realized that if they could use their money to buy politicians or buy the political process so they could get what they wanted out of their businesses.
10:42
And there's an argument historically that's made that that's just fine.
10:45
That's the key to American success.

24 MINS LATER

34:59
So, you know, we
8:03
They're now seeing a direct tie between the fact that nothing's being delivered on for them and the fact that these folks are just just so happen at the same time to be getting really, really god awful rich.
8:16
Well, in their own their own well-being and how difficult it is to get ahead and how difficult it is to feed your family and how difficult it is to secure a job that elevates you.
8:26
out of the working class into the middle class or out of the middle class into the upper middle class.
8:30
And against that backdrop of escalating gas prices, spiking electricity prices, food inflation, uncertainty about education, AI emerging in most people's minds as a jobs disruptor and this unknown force in American life, you have a president who this weekend is telling people, I want to build a world-class golf course in Washington, D.C., which is the most elite sport probably in the United States.
8:57
He spends more time focused on building monuments to himself or new golf courses and saying the affordability crisis is a hoax when it's absolutely not.
9:08
And he's now joined on the campaign trail by a politician in the form of Barack Obama, who is a dynamic, focused, policy minded man who can go and talk to candidates about the positive sides of his own party's candidates, as opposed to Trump doing cosplay with a MAGA hat on.
9:29
breaking people down in the most racially grotesque ways imaginable because all he knows how to do is divide.

7 MINS LATER

16:50
So why no consequences there? I'm sure there are other people waiting in the wings who want those jobs.
9:38
Hm
9:38
... won't try to run roughshod over Congress even if the president has the ability to do so.
9:42
We trust that a president won't sow widespread and massive distrust in the electoral process, uh, in the service of sabotaging voters' confidence in democracy and i- and in sabotaging democracy itself.
9:56
But that's what Trump has, has, has demonstrated is that he's willing to go there, and that's some of the stuff that will outlast Trump because the damage he's trying to do now in the short term I think could have really long-term legs and people just not only distrusting the electoral process, but other functions of government that, that aren't partisan, that aren't about, um, uh, someone gaining an advantage.
10:20
They're just the wheels of our society that we rely on for things to function normally, and he doesn't want those things to function normally because he wants to control each and every single one of them because he's an autocrat.
10:32
And, and i- that's not surprising about him.
10:35
You know-

12 MINS LATER

22:08
This is generally when Tim O'Brien chimes in and tells me that this all predates 2016.
4:59
You've chronicled his sort of transactional nature for many years now, and I just wonder why he keeps returning to a ploy like this when, you know, the people around him should be letting him know that it's not working.
5:13
Well, I mean, he does it, Antonia, 'cause first and foremost this is exactly who he is.
5:17
He believes that anybody, whether it's a business competitor or a political competitor or his voter or members of his party, can be bought off when either reality or their allegiance doesn't align with where he wants it to be.
5:32
And this is his latest act of desperation because he's seeing the poll numbers.
5:36
If...
5:37
And, and we all should be, you know, uh, uh, uh, hesitant to embrace the poll numbers fully.
5:43
They've been wrong before.

6 MINS LATER

11:18
... is, uh, is, is outraising Lindsey Graham's sister.
2:59
It was interesting to hear Laura Trump say the quiet part out loud.
3:03
And, you know, there was a little bit of extra, I think, spin in what she said in which she sort of suggested that disarming Iran was so important and ending Iran's nuclear program was so important that it would be worth losing the midterms.
3:19
Neither of which they've accomplished.
3:20
Neither of which they've accomplished.
3:21
And it's in keeping with this line that's come out of The Trump administration, his supporters in Trump himself, the people just have to tough it out and deal with it.
3:31
And the other people we've seen on the global stage acting that way or speaking that way is Iran's leadership, which has been willing to put its own people through incredible hardship to prosecute this war, or Vladimir Putin, who's been willing to churn through Russian soldiers' lives in Ukraine to further his goals.
3:50
And at the end of the day, Trump and his children are saying they're going to pursue this come heck or high water because they don't care about the impact on other people.

6 MINS LATER

9:44
The average mortgage rate is now 7.28% after the biggest one-week jump since October 2022.
3:51
was like taking notes where he's like, great idea.
3:52
Yes, yes.
3:53
I just don't want you to do it.
3:55
And, you know, he's never put his own money to work ever in his political life.
4:00
You know, he kept saying during his first campaign for the presidency that he was going to spend his own money.
4:06
He would spend as much money as it took.
4:08
There's no evidence he ever spent heavily.

16 MINS LATER

20:24
She asked, do you not want tough questions, sir? How important is it to combat the argument that Blanche is making that all of this is just fake news?
4:15
That's the tell.
4:16
Yeah, you know, he's in this.
4:18
This goes back to his first term.
4:19
He has an irrational reputation.
4:22
and somewhat childlike fetish for strongmen, dictators, people who command their own armies, their own voters, and their own state.
4:30
And it's a perilous time right now for him to be continuing to do that.
4:34
We're in the middle of an AI race with China that has both corporate and national security dimensions to it.
7:37
And
10:03
I think, though, election officials showing up at your polling place and saying, I would like you to give me those ballots, please, reads as a shakedown, even if you are not someone who is wildly familiar with the intricacies of American democracy and voting.
10:19
It's raw intimidation.
10:21
It's meant to be intimidating.
10:23
It's meant to make poll workers at the ground level and secretaries of state at the highest part of the electoral food chain in each state feel intimidated and cautious.
10:35
We can hope that they do have their legal artillery in place.
10:40
in 2020, no one anticipated that the Trump crew would try to get fake slates of voters, electoral voters, into the mix.
10:50
They found different holes in the armor to penetrate.

11 MINS LATER

22:23
So where does that leave us?
3:41
We haven't even mentioned grocery prices.
3:43
Yeah, and it, you know, this entire year has been a series of cell phones, and this is like a, you know, icing on the cake, certainly for Democrats, but for anybody just watching how Donald Trump, who came in in 2024 with what seemed to be a mandate, had control over his own party, had a unified Congress, and proceeded to blow up the economy, proceeded to embarrass himself on the public stage around policy issues he easily could have avoided, and has so little self-regard – no, not self-regard, self-awareness – um, that he can't help himself from staying out of this midterm race because he's gonna be a drag on GOP candidates.
4:23
He's underwater.
4:24
He's wrong on the issues.
4:26
Americans are struggling with affordability.
4:28
Part of the affordability problem is booming out of issues he's created: tariffs, the war in Iran.
4:36
And apart from affordability, he's mired us in an oversea war, overseas war that is ruining our reputation, endangering our soldiers, wasting our money, destabilizing the Middle East, and there's no end in sight.

25 MINS LATER

30:13
While the Wall Street Journal calls Jared Kushner one of the world's most powerful diplomats.
10:27
But do you think there's a strategy here? What is going on?
10:32
I always think, Eugene, it's a mistake to put strategy and Donald Trump in the same sentence.
10:38
He doesn't plan.
10:40
He's not intellectually curious.
10:41
He doesn't take the advice of advisors who have greater experience or insight than he does.
10:47
His whole life has been a triumph of style over substance and smoke and mirrors.
10:53
over reality.

20 MINS LATER

31:13
doesn't actually mean anything substantively, but it does tell you a lot about where the president's head is and what he's trying to signal to our allies here.
43:33
Canada has been the country that every single American president had the easiest time with of any country on the planet
43:42
Because they're easy to get along with, Lawrence.
43:45
[laughs]
43:45
You- Canada and Mexico, uh, together represent our most significant global trading partnership.
43:51
Canada's a democracy.
43:53
We have a shared history with Canada.
43:56
Uh, they have a rich culture.
43:57
They have been good neighbors in the deepest sense of that term.
5:09
Tim, the White House has gotta see this as a win.
5:13
Uh, I don't know if they see it as a complete win, Steph, 'cause they're not com- You know, they, they're, they are able, as Harry pointed out, to inject uncertainty in, into an election that shouldn't have uncertainty entering the dialogue right now.
5:25
But certainly at work here is the Supreme Court's exposed again for multiple hypocrisies and legal inconsistencies.
5:33
Harry put his finger on this issue of who's damaged and who isn't.
5:36
They somehow said that the, the White House and the president is damaged because he can't be forbidden from running the post office as he sees fit.
5:46
But the attorney generals who are suing to prevent this from happening can't say they're damaged because damage hasn't been demonstrated yet.
5:54
But of course, the damage to be demonstrated in this would be that voters would, would be denied access to the polls, and that, uh, essentially constitutional democracy would get uprooted.
11:04
Yeah
38:35
I think in the second term, Trump has made a fool of all those people in the first term who bet coincidence.
38:42
Yeah, I, I guess I would, I would, I would tweak that a little bit to say that it was just low-level corruption in the first term.
38:48
Like the Trump Hotel near the White House where the Saudis would take out entire floors, uh, prior to meeting with officials in the White House.
38:56
Uh, all of that stuff is such small change compared, as you note, to what we're seeing now in, in, in Trump 2.0. He's made billions of dollars on crypto alone.
39:06
No other president in any era in the United States has been this craven and this hungry to turn the White House into a casino and, and just harvest money regardless of the impact it has on the reputation of the presidency, um, the creation of, uh, non-partisan, socially responsible policy, et cetera, et cetera.
39:28
And it- and as you noted in, in the top of this block, uh, the timing of, of this Truth Social business opportunity is, is pretty extraordinary because when all of this stuff emerged that, you know, I think it was around $760 million [laughs] in oil contracts were moving ahead of big policy announcements from the White House, um, when it- dozens of accounts got set up on either Kalshi or Polymarket prior to the Iran invasion.
39:56
Uh, there was a suspect- suspicious trading around Venezuela prior to Maduro being snatched, and the White House warned, uh, staff not to do that kinds of stuff 'cause it was, those things, it, it was bad.
41:56
Who knew? I mean, w- what do you make of the willingness to, of the sons to enrich themselves based on their father's position?
27:58
Okay
27:59
... and they're, but they're, but they're bad for different reasons.
28:02
And, and, uh, on, on the one hand, you know, you've got Congress, which constitutionally is meant to retain the power of the purse, and so many times in this administration a Republican-controlled Congress has simply allowed the President to run circles around them.
28:19
And it's not just a, a matter of prerogative or power, it's about making sure money isn't, uh, improperly appropriated or improperly allocated, and that American taxpayers know what is being done with their hard-earned, uh, wages that have been turned into tax payments to the federal government.
28:40
It's particularly peculiar, troubling, and bad that a Republican administration is doing this when historically Republicans have inveighed against, uh, the misuse of tax dollars and big government.
28:53
So that's problematic.
28:54
Um, secondly, it, it is problematic that taxpayers have to foot what is essentially a gargantuan vanity project that's being routed in a very nebulous and opaque way, by design, I believe.

5 MINS LATER

34:22
Some of what Trump, uh, tweets, bleats, whatever verb you're supposed to use, moves markets, and if you are a Wall Street firm, do you basically have to buy a subscription to remain competitive?
18:22
T- Tim, why wouldn't the Trump donate the jet to the library, and what is the biggest conflict of interest problem in your mind for the public?
18:30
public?... a lot of money.
18:35
And the Trumps, when they see anything in front of them that's worth a lot of money, they take it, whether it's crypto or resort deals in the Middle East, um, or, uh, giant jets that they're getting from a foreign government that presents possible national security concerns, uh, for the American voters and for the national security apparatus in Washington.
18:57
You know, Vaughn, um, uh, Liz, Liz Smith, the late, great New York Daily News gossip columnist once said to me, um, in, in her Texas drawl, "You know, honey, the only thing you need to know about Donald Trump is that he's a seven-year-old grown old." And like a seven-year-old, Donald Trump loves his toys, and he loves to surround himself with bling.
19:20
He, he lives in a triplex in Trump Tower that looks like the high roller's, uh, suite at, at Caesar's Palace.
19:28
He's...
19:28
Obviously, he loves gold.
22:19
But where do you see the ability to try to reign in some of these conflicts of interest? Is it Democrats potentially seeking super majority to overcome his veto with Republicans in 2027? Or is this even a move as late as 2029, actions taken now that could have impact more of almost two and a half years from now?
20:32
That has an impact on the Hill.
20:34
It has an impact on the Hill and it has an impact on the American public.
20:37
Science and vaccines are good things in a healthy society.
20:44
And when you start to tell public servants who could go into the private sector, like Anthony Fauci could have done, during any time in his career and stayed there and reaped the rewards financially from doing that, but chose instead to be a public servant, that any mistake you made during your service to the country could get weaponized against you and your reputation gets shredded, your sense of your own safety in our society gets shredded.
21:11
We're in a perilous place and it's also happening to Jack Smith.
21:14
He's being chased around the block for prosecuting two very viable cases that involve the president.
21:21
The most recalcitrant operator and figure during the whole COVID episode was Donald Trump.

6 MINS LATER

27:14
And I'm wondering if this administration starts looking for someone to eventually throw under the bus, does it end up being Hegseth?
12:46
Tim, you got to wonder, was the immunity deal the real prize all along?
12:51
Oh, I absolutely think it was.
12:53
I think, you know, both parts of that deal accomplished different things.
12:57
The slush fund was a way for Trump to engage in more performance out around January 6th and reward people who shouldn't be rewarded in many cases for bad behavior at a minimum.
13:11
The audit deal is an extraordinary thing.
13:14
Trump originally sued the IRS for $10 billion.
13:20
That was, I'm assuming, far more than everyone would have gotten, but it put a price tag on what I think the audit part of this, how valuable it was to him.

7 MINS LATER

20:56
One is, what is sort of like the macro danger of the IRS piece of this, given that this is a president where you give him an inch, he takes a mile? But two, if Democrats are to take back either, both chambers in November, how do they then make sure there's some accountability?
19:05
They went to a convicted mob boss and killer in order to do it.
19:09
Well, you know, for context's sake, Donald Trump has always fancied himself as a mob boss.
19:15
You know, when I was working my book and interviewing during that period, he constantly told me how much he admired John Gotti because John Gotti sat in the courtroom and said F you to the judges and didn't take grief from anyone.
19:28
Donald Trump's also a classic bully.
19:29
As much as he fetishizes machismo and the mob, he is averse to direct confrontation.
19:36
He often buckles under that kind of pressure.
19:41
He should take a lesson that when even Sammy the Bull, is telling you you have your mob argot wrong.

16 MINS LATER

35:23
But if that's the feedback they're getting and Nebraska won, what's it going to be like everywhere else?
3:35
I didn't realize they were so extensive.
3:38
Yeah, so, you know, there's a, I'm not surprised that you mentioned that.
3:42
There was, of course, a long story history of ferries in New York that, you know, dating back to, you know, the early days of development of City.
3:53
And, of course, there were, you know, some of the listeners will know that, you know, the bridges, the development of many of the bridges, the Brooklyn Bridge in particular, kind of undercut, you know, the rationale for there being quite so many ferries in New York Harbor.
4:08
Over the years since then, there have been some ferry operations.
4:12
Obviously, the Staten Island Ferry is a major link within New York Harbor.
4:17
And for many years, there have been New York City to New Jersey passenger vessel operations.
7:03
Talk to us about your business model and how Hornblower operates both domestically and then offshore.
40:38
How far might this go, Tim?
40:41
Well, it's going to go as far as I think the Trump family's own greed and appetites take them because there's no one really standing in the way of this, Alex.
40:52
The GOP, you know, the Law and Order Party is doing absolutely nothing to restrain it.
40:58
There have been no congressional hearings looking into this.
41:02
President Trump controls the regulatory agencies and the law enforcement agencies that would normally look into this kind of public corruption, which is what it is.
41:13
This isn't legitimate business activity by the Trumps.
41:16
Donald Trump Jr. isn't earning 200% returns and adding hundreds of millions of dollars to his wallet because he's uniquely talented or an excellent money manager with a long track record on Wall Street of investment prowess.
42:09
And then last year, while Trump was president.
32:31
Were either of the Trump sons successful investors before Donald Trump was president a second time?
32:38
You know, Nicole, there's this old, um, Steve Martin joke, I think from, like, the '70s, that went, uh, uh, "I'm gonna teach you how to become a millionaire.
32:46
Step one, find a million dollars." And, and the Trumps have updated that, uh, basically to, "I'm gonna tell you how to become a billionaire.
32:56
Become president of the United States, and then your children can also share in the riches." Because the only reason that Donald Trump, his son-in-law, Jared Kushner, and his two eldest sons are raking in the money like this is because Donald Trump sits in the Oval Office.
33:12
There's absolutely no other reason for it.
33:15
Donald Trump Jr.'s first job when he finished college was as a bartender, and then he went to work for his father.
33:22
None of it involved investing or managing money at this scale with eye-popping returns that most professional managers who have a lifetime of experience and expertise and insight into financial markets, and on and on and on, could never match.

6 MINS LATER

39:11
[laughs]
35:25
Mm-hmm.
35:25
Um, it's the federal government ...
35:27
Actually, their subpoena goes back to January.
35:29
So they're actually asking for sourcing information that predates any of the reporting about the Qatari jet.
35:36
Uh, they've subpoenaed, uh, uh, one of the reporters' wives and one of the reporters' mothers.
35:42
Now, with the national security blanket on this, they may be able to pierce the spousal privileges around testifying against your spouse, but that's also nonetheless unusual.
35:52
Um, when Trump sued me, um, during the deposition, uh, I did two eight-hour depositions with Trump's legal team.
40:02
Does this add up?

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