In Conversation with Dean Obeidallah
23 May, 2026
[Transcript edited for clarity, flow and length]
I got to hang out with my friend and fellow Nerd Avenger, Dean Obeidallah, and we covered a lot of ground, including Donald’s slush fund, his obsession with the ballroom, Stephen Colbert’s final show, and Donald’s predictably petty response to it. We also tackled one very important question: How long has Donald actually known his oldest son? Enjoy.
Dean Obeidallah: Welcome to The Dean Obeidallah Show. Joining us right now is our friend Mary Trump, activist and bestselling author of Too Much and Never Enough: How My Family Created the World’s Most Dangerous Man. Her Substack is The Good in Us by Mary Trump, and her YouTube channel, Mary Trump Media, is wildly popular. Mary, it’s great to see you.
Mary Trump: Dean, it’s great to see you too. I apologize for the circumstances, but what else can we say at this point?
Dean Obeidallah: There’s a lot to cover. From both a family perspective and your background as a psychologist, Donald Trump seems uniquely unable to tolerate being mocked. Before politics, he sued Bill Maher over a joke. He fought publicly with Jon Stewart. As president, he tried to pressure networks over late night hosts. Now he’s celebrating Stephen Colbert leaving CBS, saying Colbert is finally finished and calling him talentless. Why does mockery get under his skin so deeply?
Mary Trump: Because he knows what a pathetic loser he is. He knows it’s all pretense and smoke and mirrors. What terrifies him is the possibility that more people will finally see him for who he really is.
Most people with any sense already do, but he’s had a tremendous amount of help perpetuating the myth that he’s a brilliant businessman and self made success story. He’s also deeply threatened by people who actually have talent because he doesn’t.
Dean Obeidallah: He also wants fear, not laughter. Dictators hate being mocked because ridicule strips away power. Donald wants people intimidated by him.
Mary Trump: Exactly. But the irony is that every time he attacks somebody like Colbert or Kimmel, he only elevates them. If he were actually strong, he would ignore it. Instead, he reacts emotionally every single time because he’s profoundly insecure.
And let’s be clear, the reason people cater to him now is because he sits in the Oval Office. That office comes with enormous power, and people around him want things from him. It has nothing to do with Donald himself being powerful.
Dean Obeidallah: Do you think it bothers him that he’ll never be loved the way somebody like Stephen Colbert is loved?
Mary Trump: Honestly, the reason we’re in this mess is because Donald has never been loved. That’s the tragedy at the center of all of this.
Because of the way my grandfather raised him, Donald became somebody who desperately wants to be loved but who is fundamentally unlovable. He’s incapable of intimacy, empathy, or genuine connection.
And he knows it. That’s where the rage comes from.
Dean Obeidallah: We saw another example of that recently when Donald was asked whether he’d attend Donald Trump Jr.’s wedding. He said he’d “try” to make it because he has “Iran and other things” going on. This is a man who golfs constantly but apparently cannot commit to attending his own son’s wedding.
Mary Trump: It tells you everything. Donald is incapable of loving people in a healthy way. Why would anybody expect him to behave like a normal father?
And honestly, the way he referred to Don Jr.’s fiancée as simply “a person I’ve known for a long time” says a lot too. There’s no warmth there.
Dean Obeidallah: Let me ask you as a psychologist. Many people are noticing changes in Donald’s behavior. He falls asleep publicly. He lashes out impulsively. He seems increasingly erratic. What are you seeing?
Mary Trump: I’m not a neuropsychologist, but I am somebody whose grandfather suffered from Alzheimer’s disease. Some of the behaviors we’re seeing, like falling asleep during the day and the increasing lack of impulse control, can absolutely be associated with cognitive decline.
But I also think we’re watching the continued deterioration of somebody who has had serious psychiatric issues his entire life that were never treated. Untreated disorders worsen over time.
Part of why he’s becoming more volatile is because, on some level, he knows he’s losing control. He’s losing control of the narrative and increasingly losing control of himself.
Dean Obeidallah: Dr. John Gartner recently said Donald now seems to enjoy violence in a way that’s become more pronounced. During the first term he was chaotic, but now there’s something darker.
Mary Trump: I don’t think he’s fundamentally changed. I think the deterioration is simply revealing who he has always been.
Donald has always been violent psychologically. He has always reveled in cruelty. Remember when he encouraged police officers not to be “too nice” with suspects? Remember how he talked about immigrants committing crimes?
The difference now is that he no longer has whatever minimal restraint he once possessed.
Dean Obeidallah: And nobody around him tells him no anymore.
Mary Trump: Exactly. Nobody around him has the courage or integrity to push back. That’s part of why everything escalates.
Dean Obeidallah: We also learned about the massive settlement involving January 6 defendants and the IRS. Any functioning attorney general would recognize how corrupt this looks, but nobody in this administration seems willing to object.
Mary Trump: It’s grotesque. We still haven’t seriously addressed the lasting economic and social damage caused by slavery and systemic racism in this country, but suddenly there’s endless money available for insurrectionists who violently attacked police officers.
And let’s not pretend this was accidental. The administration knows exactly what it’s doing. Donald surrounds himself with people who invent increasingly corrupt schemes because corruption is now the organizing principle of this administration.
Dean Obeidallah: Tulsi Gabbard also resigned abruptly this week. What do you make of that?
Mary Trump: Honestly, I think she was likely on her way out anyway. She had clearly been sidelined.
But this administration is filled with deeply unqualified people, so her departure doesn’t exactly solve anything. We still have Pete Hegseth, Kash Patel, and others who should never have been entrusted with public office.
Dean Obeidallah: Do you think Donald eventually pardons everybody around him?
Mary Trump: Absolutely. I think he’ll hand out pardons broadly because he understands how vulnerable everyone in his orbit is legally.
And frankly, one lesson we should take from all of this is that presidential pardon powers need serious reform. Every president has abused power in some way, but what we’re seeing now is corruption on an entirely different scale.
Dean Obeidallah: You’ve said before that this isn’t just about Donald Trump. Can you explain that?
Mary Trump: Donald is obviously dangerous, but he is also a symptom of much larger failures. The Republican Party enabled him. Media institutions normalized him. Wealthy interests benefited from him.
Even after January 6, Republicans had opportunities to stop him and chose not to. That tells you this problem runs much deeper than one man.
Dean Obeidallah: So where does that leave us?
Mary Trump: It means we need to stop pretending any of this is normal. We need to stop assuming institutions will automatically save us.
The good news is that more people are paying attention now because Donald’s failures are affecting them directly. The bad news is that democracy requires active participation. It requires vigilance.
Dean Obeidallah: Before we go, where can people follow your work?
Mary Trump: People can find me at The Good in Us on Substack and at Mary Trump Media on YouTube. I’m also on social media and Patreon.
Dean Obeidallah: Mary, always great to see you. Thanks so much for joining us.
Mary Trump: Thanks, Dean. Always good to see you too. Check out Dean’s Substack below.
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TRUMP OUTDOES HIMSELF IN DETONATING ANOTHER DISTRACTION FROM HIS CORRUPTION AND PERVERSIONS
Yesterday, Trump ordered the deportations of hundreds of thousands of people with jobs, homes and families in the U.S., who are awaiting the processing of their applications for Green Cards, to return to their countries of origin to apply for permanent visas. It is expected that ICE agents will be taking the lead in physically enforcing this order.
As cruel and bizarre as this action may be, it may not necessarily be attributed to Trump’s madness, viciousness and mental instability. On the contrary, it may fit his crafty pattern of creating a crisis as a strategy to deflect the public’s mind off of far more serious misconduct by Trump himself.
Trump’s action today to order his goons to eject hundreds of thousands of residents awaiting green cards appears to fit a pattern that we have been increasingly seeing ever since he first discovered how his initial surprise bombing of Iran almost totally distracted the American people from the utterly humiliating birthday military parade he threw for himself.
Trump thereafter deployed this strategy of distractions on occasions when he was faced with political setbacks, potentially humiliating disclosures, or other occasions when his poll ratings took a deep dive. His most blatant distractions have been during the Epstein hearings and disclosures and included his indiscriminate murders on the high seas of drug smugglers, whom he renamed “narco-terrorists” to make them more target justifiable, his invasion of Venezuela and the arrest of their President, his threats to seize Greenland, his second wave of bombing of Iran and this threats to destroy their civilization unless they submitted to his will.
It is not coincidental that Trump’s order today to eject these hundreds of thousands of residents from the U.S., comes within hours after Trump was thoroughly humiliated by the revelation that his own party has refused to fund his gold encrusted ball room and, more importantly, refused to support the plot he worked out with his Acting Attorney General to divert $1.7 billion dollars in taxpayer money to a slush fund for him to personally control and disburse, including payments to his co-conspirators who who were convicted after trial of storming the Capitol and leaving dead bodies in their wake.
There is, of course, the issue of whether Donald Trump, alone and unilaterally without the consent of Congress, has the sole right to arbitrarily order that these hundreds of thousands of residents awaiting green card be ejected from the United States. It’s inconceivable that Trump has this unilateral right.
For one thing, while not legally applicable, Trump’s order smacks of an ex post facto order or law. An ex post facto law, which is prohibited by the U.S. Constitution, is a law that retroactively makes conduct criminal, increases punishment, or worsens the legal consequences of an act after it was committed. Simply put, the government can’t say, “That thing you did last year was legal then, but we now declare it criminal and punish you for it.” While, this doctrine may not literally apply to Trump’s order today, the principle does. These people have been here legally and awaiting the processing of their green card applications. They have jobs, homes and families here. It is simply unfair, un-American and so alien to our inherent sense of fairness to allow Trump’s unilateral order to be enforced.
But perhaps that is not Trump’s end game. Given Trump’s utter humiliation in being denounced for expecting the American taxpayers to pay $500 million for his gold-encrusted ballroom and another $1.7 billion taxpayer dollars for his personal slush fund to disburse as he pleases, Mr. 3-Card Monte needed an immediate shock-wave to get the American people to look the other way, and that’s what this is really all about.