In Conversation with Dean Obeidallah

1 July, 2026

[Transcript edited for clarity, flow and length]

Mary Trump: I got to talk with my friend and fellow Nerd Avenger, Dean Obeidallah, and we covered all of the latest Supreme Court decisions, from the egregious to the dispiriting, plus, of course, the fact that once again E. Jean Carroll kicked Donald’s ass, proving once and for all that he’s a complete and total loser. We talked about that and a lot more, so please enjoy.

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Dean Obeidallah: Welcome back to The Dean Obeidallah Show. Joining us now is Mary Trump, bestselling author, activist, creator of The Good in Us on Substack, and the force behind Mary Trump Media. Mary, it’s great to see you, my friend. I hope you’re here to help us make sense of everything. You’re a trained psychologist, so I think we could all use a little therapy right now.

Mary Trump: It’s great to be here. I’m not entirely sure I can make anybody feel better because I think that’s one of the biggest misconceptions about therapy. It’s a long term process, and it doesn’t necessarily make things better in the short run.

Part of that process, though, whether it’s individual therapy or putting the entire country on the couch, is facing what we’re actually dealing with. We need to take some ownership of whatever responsibility we have for where we are, understand the impact other people have had on our lives and on our country, and then figure out how we move forward.

The good news is that, as bad as things are right now, history tells us that these darker moments often create the greatest opportunities for real, transformational change. I think we’re at one of those moments because people are finally beginning to notice what’s happening.

Dean Obeidallah: There are certainly things that give us hope. One of them is E. Jean Carroll’s latest victory.

The Supreme Court denied Donald Trump’s appeal in the $5 million defamation case, the one in which a jury found him liable for sexually abusing E. Jean Carroll and then defaming her. The Court refused to hear the appeal, so Donald now has to pay.

What can you share about E. Jean’s reaction?

Mary Trump: E. Jean is, of course, ecstatic, and so is her legal team. They deserve to be. This has been a very long time coming.

The Supreme Court held onto this case for months, and that was frustrating because the longer they delayed, the more it felt like they might actually decide to hear it, which they never should have done.

Thankfully, they didn’t.

For anyone worried that E. Jean won’t actually receive the money, that’s not an issue. Because of the delay, the judgment has continued accruing interest while sitting in escrow. The money is already there. Nobody has to chase Donald down or seize assets.

Hopefully, we’ll now see the same thing happen with the much larger $83.3 million judgment, which is also sitting in escrow and continuing to accrue interest.

The only remaining issue there is Donald’s argument that, because he was president when he defamed her, he somehow acted in his official capacity. I’ve spoken with people who understand these issues far better than I do, and they think that argument is very unlikely to succeed.

Regardless, this judgment is final.

Forever and for all time, Donald Trump is officially an adjudicated sexual abuser who defamed E. Jean Carroll. There is nothing he can do to change that.

Dean Obeidallah: That’s exactly right. The money is already sitting in escrow, so it simply has to be released to E. Jean Carroll.

Unfortunately, today’s Supreme Court news wasn’t nearly as positive.

The Court upheld Tennessee’s law restricting gender affirming care for transgender minors. In practical terms, it’s another decision allowing discrimination against one of the most vulnerable groups in America.

Justice Sotomayor pointed out in dissent that the Court refused to take a nuanced approach. The plaintiff in this case had received puberty blockers from the beginning, meaning none of the arguments about competitive advantages even applied. Yet the Court still upheld the law.

What’s your reaction?

Mary Trump: I think this corrupt, illegitimate supermajority has made its priorities perfectly clear.

They’re determined to rip the Constitution to shreds, ignore decades of precedent, and advance an ideological agenda rooted in cruelty.

Just as Donald has made cruelty a defining feature of his regime, this Court seems intent on making cruelty a constitutional principle.

They’re systematically stripping rights away from the most vulnerable Americans.

To put this into perspective, transgender people make up less than one percent of the American population.

Now ask yourself what percentage of that one percent consists of transgender children who simply want to play sports at school.

We’re talking about an extraordinarily small number of children.

I don’t pretend to know everything about transgender participation in professional athletics, and that’s not what this case is about.

This is about children who simply want to participate in school activities with their friends as the people they know themselves to be.

They’re not competing for Olympic medals. They’re not taking away professional contracts. They’re children who want to belong.

Apparently, even that has become unacceptable in America.

The enthusiasm with which this Court continues targeting one of the smallest, most vulnerable populations in the country is both alarming and revealing.

It tells us everything we need to know about the values driving this majority.

Dean Obeidallah: Justice Sotomayor’s dissent really captured that humanity. Before 2016, states like West Virginia evaluated these situations individually. They looked at each student’s circumstances and made decisions case by case.

Republicans replaced that with blanket bans because cruelty became politically useful.

I don’t understand why cruelty brings these people so much satisfaction.

Mary Trump: Neither do I, except that we now live in a political culture where cruelty is rewarded and bullying is celebrated.

We also have to acknowledge that at least several members of this corrupt Supreme Court have accepted extraordinary gifts and benefits from billionaire benefactors. Whether it’s ideological extremism or outright corruption, the result is the same.

They’re deciding cases based on ideology and power, not justice.

Then you have the true ideologues whose understanding of fairness has been completely distorted by their belief systems.

Either way, we’re facing a Court that has abandoned its responsibility to the Constitution, and we have an enormous amount of work ahead of us.

Dean Obeidallah: Let me ask you this. How important is Supreme Court reform as an issue for Democratic candidates heading into 2028? Is it something they should mention occasionally, or should it be central to their campaigns?

Mary Trump: If you’re a Democratic candidate running for anything in this country and you’re not committed to meaningful Supreme Court reform, don’t bother running.

We need leaders who will promise, and then actually follow through, on expanding the Court by at least four to six seats. We need a real ethics system with actual enforcement. We need term limits and other structural reforms. At a minimum, Justices Clarence Thomas and Samuel Alito, and perhaps Brett Kavanaugh, should be investigated, and if warranted, impeached.

It cannot continue to be left up to these justices to decide for themselves when they should recuse. They cannot continue accepting lavish gifts, luxury vacations, and favors from billionaire benefactors while deciding cases affecting those same interests.

It’s disgraceful.

Just as we need to eliminate the filibuster, grant statehood to Washington, D.C., and Puerto Rico, and address other structural problems in our democracy, Supreme Court reform has to become a central part of every Democratic platform.

Anything less simply isn’t adequate for the moment we’re living through.

Dean Obeidallah: I love how blunt you are. If you’re not willing to commit to Supreme Court reform, don’t bother.

By refusing to address it, you’re effectively saying the Court is functioning properly, and it clearly isn’t.

Unless something changes dramatically, we’re looking at a six to three Republican majority for decades. The Court is becoming more aggressive every year. They’re striking down laws, giving more power to presidents, making it easier for billionaires to dominate elections, weakening voting rights, and now authorizing discrimination against transgender Americans.

This Court is out of control, and Congress has both the authority and the constitutional power to reform it.

Mary Trump: We need to be equally blunt about something else.

This Supreme Court has become an enemy of the Constitution.

It reflects the views of perhaps thirty percent of the country, not the American people as a whole.

People also forget that the Constitution never fixed the number of Supreme Court justices. Throughout our history, the size of the Court has changed.

Republicans effectively changed the size of the Court themselves when they refused even to give Merrick Garland a hearing, leaving the Court with only eight justices for nearly a year.

Expanding the Court isn’t radical. It’s constitutional, it’s been done before, and it may be the quickest way to interrupt the constitutional chaos this Court continues creating.

Dean Obeidallah: I couldn’t agree more.

Let’s shift gears.

We’re approaching the 250th anniversary of the United States. If the Founders came back today and saw what Donald Trump has become, do you think they’d encourage Americans to rise up against him the way they rose up against King George?

Mary Trump: I think the first thing they’d ask is, “When did everybody become so unbelievably foolish, and how did this man get elected twice?”

Once they recovered from that shock, I absolutely believe they’d tell Americans to rise up because Donald Trump is exactly the kind of would be monarch they fought a revolution to escape.

They created this country specifically to reject hereditary power, unchecked executive authority, and the idea that one man should place himself above the law.

Donald represents the very system they rebelled against.

Dean Obeidallah: I actually wrote about that recently.

If Donald Trump had been alive in 1776, I have no doubt he would have sided with King George.

The wealthy elites in New York overwhelmingly supported the British Crown because they were protecting their own wealth and privilege. Donald would’ve fit right in.

He certainly wouldn’t have risked everything alongside ordinary colonists fighting for democracy.

Mary Trump: No, he wouldn’t have.

Look at what he says today.

He calls affordable housing “a big yawn.” He says he wants housing prices to go higher, not lower.

He’s always made it perfectly clear where his loyalties lie. The tragedy is that people have taken so long to believe him.

Dean Obeidallah: When you knew him years ago, did he already have these ambitions of becoming a king or dictator?

Mary Trump: He always believed he deserved more than everyone else.

He always believed he was better than everyone else.

But he wasn’t especially interested in politics beyond whatever affected the Trump family business and New York real estate.

Still, it doesn’t surprise me that he’s developed these imperial ambitions because Donald has never believed there is such a thing as enough money or enough power.

He wants people to believe it’s because he’s uniquely gifted and uniquely deserving. That’s the myth my grandfather spent years creating about him, and it’s a myth Donald eventually embraced himself.

In reality, it’s all compensation for overwhelming insecurity.

On some level, Donald knows exactly who he is.

He knows he isn’t the brilliant businessman he’s pretended to be for decades.

He knows he’s profoundly incompetent.

Everything else, the money, the power, the monuments, the branding, serves only one purpose: protecting him from that truth.

Dean Obeidallah: One thing that still puzzles me is Donald’s complete indifference to the struggles ordinary Americans are facing. He recently dismissed concerns about affordable housing, calling it “a big yawn,” and when inflation came up, he essentially said he didn’t care.

Politically, that makes no sense because even Republican voters are struggling with higher prices.

Do you think he genuinely doesn’t care, or does he simply believe none of it matters because he’ll never be held accountable?

Mary Trump: Donald has never cared about anybody but himself, so none of this surprises me.

I also don’t think he cares about the Republican Party except to the extent that it protects him and allows him to remain in power. They’ve demonstrated over and over again that they’re willing to do exactly that.

As for inflation, housing prices, and the economy generally, what you’re seeing is another example of Donald trying to normalize his own failures.

He spent years promising he’d lower inflation and make life more affordable. Instead, because of his reckless and deeply misguided policies, inflation has increased and housing has become even more expensive.

Rather than admit failure, he simply changes the narrative.

If inflation is high, then suddenly high inflation is a good thing.

If housing becomes unaffordable, then expensive housing becomes desirable.

It’s classic gaslighting.

Unfortunately, that strategy works on a great many people because they’re no longer evaluating reality independently. They’re accepting whatever narrative Donald tells them to believe.

Dean Obeidallah: People have also noticed the bruising on Donald’s hands, the makeup covering them, the swelling in his ankles, and some of the marks on his neck.

Given your family’s history, do you have any thoughts about what’s happening physically?

Mary Trump: I’m not a physician, so I can only speculate.

The bruising on the backs of his hands makes me wonder whether he’s receiving intravenous medications because repeated IV access can certainly produce bruising like that.

Beyond that, though, we can all observe what’s in front of us.

There’s the swelling in his hands and ankles, the fact that he appears to fall asleep repeatedly during the day, his difficulty walking normally, and the increasing frequency with which he seems confused or loses his train of thought.

None of that paints a reassuring clinical picture.

We also know that Donald himself has talked repeatedly about taking cognitive assessments. He’s reportedly undergone multiple physical examinations in a relatively short period of time, seen numerous specialists, and received repeated imaging studies.

Whatever is happening, it doesn’t suggest someone in robust health.

Dean Obeidallah: Did you observe anything similar in your grandfather during his final years?

Mary Trump: My grandfather lived with Alzheimer’s disease for quite some time.

Looking back, I believe the earliest signs probably began around Donald’s current age, although they weren’t immediately obvious.

Initially it was small things. His short term memory wasn’t what it had been. His impulse control changed. Then, once the disease reached a certain point, the decline accelerated dramatically.

Eventually he struggled to recognize people, repeated the same stories countless times every day, and often appeared confused about where he was.

Sometimes, when I watch Donald now, I see flashes of that same expression my grandfather had, almost a deer in the headlights look, when he suddenly seemed uncertain about his surroundings or the people around him.

That doesn’t mean I know what Donald’s diagnosis is. None of us do, and given this White House’s willingness to conceal information, we may never know.

But taken together with the physical symptoms, the apparent cognitive changes, and the repeated medical evaluations, it certainly raises serious concerns.

Unfortunately, if cognitive decline is what’s happening, it doesn’t improve over time. It only progresses.

Dean Obeidallah: That’s one of the most troubling aspects of this situation. If the American people aren’t being told the truth about the president’s health, then we have no idea who’s actually making decisions behind the scenes or how often Donald is truly capable of performing the job.

Before I let you go, though, I want to talk about something much more hopeful.

You and your wife, Ronda, recently launched Mary Trump’s Transcend PAC. Tell us about it.

Transcend

Mary Trump: Ronda and I are incredibly excited about this project because, as difficult as this moment is, history also teaches us that periods like this create opportunities for lasting change.

We need leaders who understand exactly what’s at stake and who are prepared to meet this moment with courage instead of treating it as politics as usual.

Far too many elected officials continue behaving as though our institutions aren’t under attack, and that’s simply not reality.

We need transformational leadership.

We need people who understand that public service actually means serving the public.

Our political system has become deeply corrupted, due in no small part to decisions like Citizens United and the enormous amount of money now flowing through our elections.

Too many people enter politics because they expect to enrich themselves, either while they’re in office or after they leave it.

We want to help change that.

Our goal is to identify and support candidates who are genuinely committed to serving the American people, protecting democracy, and helping build the multicultural, representative democracy this country has always aspired to become.

That’s the future we’re working toward.

Dean Obeidallah: I think that’s exactly the kind of leadership people are looking for.

Where can people find more information?

Mary Trump: The website is marytrumptranscendpac.org. Mary Trump's Transcend PAC

Of course, donations help, but more than anything, we’d love people simply to sign up and stay connected.

In July we’ll begin announcing our first slate of endorsed candidates, and we’re excited to introduce people to leaders we believe are ready to meet this moment.

Even if someone can’t contribute financially, staying informed, sharing our work, and helping spread the word makes an enormous difference.

Dean Obeidallah: Mary, thank you so much for joining me. It’s always great talking with you.

I hope you and Ronda have a wonderful Fourth of July, and I look forward to seeing everything Transcend PAC accomplishes.

Mary Trump: Thank you. It’s always wonderful talking with you. Thanks to everyone for joining us today.

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