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Who is the biggest alleged grifter in the Trump administration? - The Briefing with Jen Psaki | Wave AI Podcast Notes

Who is the biggest alleged grifter in the Trump administration?

Fri Mar 20 2026

Jen Psaki looks at some of the happy talk the Trump administration is offering about Donald Trump's war on Iran while outward signs suggest things are not going as well as they would have hoped.

Summary

Podcast Summary: The Briefing with Jen Psaki Episode: Who is the biggest alleged grifter in the Trump administration? Date: March 20, 2026

Episode Overview

This episode, hosted by Rachel Maddow on behalf of Jen Psaki, delves into two major, intertwined themes: the fallout from Trump’s ongoing war with Iran and several explosive reports of alleged corruption and self-enrichment among Trump administration figures—including Jared Kushner, Corey Lewandowski, and Don Jr. The episode features in-depth discussion, notable exchanges, and interviews with Senator Jon Ossoff and Congressman Robert Garcia, both of whom are engaged in congressional oversight of the administration. The tone throughout is urgent, critical, and often incredulous as Maddow and guests dissect the administration’s conduct and the repercussions across economics, national security, and public trust.

Key Discussion Points & Insights

1. The Afghanistan Iran War: Chaos, Gaslighting, and Missing Objectives

Media Narrative vs. Reality
- Maddow opens by breaking down the Trump administration's denial and obfuscation regarding the war’s success, the lack of clear objectives, and economic fallout ([01:00]–[05:23]).
- Trump and staff repeatedly claim the war is nearly won and that the economic impact isn’t “that bad,” despite clear evidence to the contrary ([02:04], [08:03]).
Escalations and Consequences
- Israeli strikes, Iranian retaliation, and US coordination (or denial thereof) have triggered global oil shocks ([02:35]–[04:29]).
- Reporting surfaces about increasing troop deployments and ballooning war costs, with Pete Hegseth attacking the media for “mischaracterizing” the conflict ([05:01], [06:55]).
- Senator Tim Kaine recounts the administration’s stonewalling of public war oversight:
  
  “I have decided that we will not have public hearings because I do not believe the administration's decision makers should be subject to Public questioning by senators.” ([09:52])

2. Economic and Popular Backlash

Pain at the Pump and in Daily Life
- Maddow highlights skyrocketing gas prices, a pause in job growth, and global market instability ([02:35]–[12:58]).
- Fishermen and other Trump supporters in impacted industries express regret and anger:
  
  “Just please think about the people, man, what are we really doing there besides raising our prices?” – Florida fisherman ([12:23])
Polling
- Americans disapprove of the war by a 22-point margin (Reuters/Ipsos), and even Trump’s base is losing faith ([12:58]).

3. Legality and Accountability

Congressional Pushback
- Senator Jon Ossoff details Senate resistance to a $200 billion war funding request, bipartisan doubts, and concerns about the war’s open-ended objectives ([15:12]–[17:14]).
- Confusion and inconsistency regarding oil and gas sanctions, particularly any moves to ease sanctions on Iran or Russia, further muddy administration strategy ([16:39]–[18:22]).
- Ossoff exposes the “Dear Leader problem” within intelligence—where officials twist themselves to never contradict Trump:
  
  "Because in this administration it is unacceptable ever to contradict the President's words. And because the President is a pathological liar, our intelligence officials twist themselves into knots.... This corrupts the process of intelligence analysis and that can lead to huge policy errors that put the American people at risk." ([20:05])

4. Widespread Corruption: The New “Biggest Grifter” Contenders

Corey Lewandowski
- Allegedly sought bribes from major DHS contractors, especially private prison groups, in exchange for contracts while officially an unpaid special government employee ([27:00]–[34:38]).
- NBC report alleges pay-to-play, with internal DHS concern about Lewandowski’s and Kristi Noem’s roles and relationships.
Donald Trump Jr.
- Don Jr.'s VC firm invests in a rare-earth startup; three months later, the startup receives a massive government contract, and its valuation explodes. Parties deny connections, but timing raises alarms ([28:00]).
Jared Kushner
- Amid ongoing conflict, Kushner is reported to be soliciting billions in investments from Middle East countries for his private firm, while simultaneously negotiating Middle East policy as Trump envoy.
- Congressman Robert Garcia, leading a new investigation, says:
  
  “What Jared Kushner is doing clearly stands against ethics principles, laws of separation of powers, and the private sector... we have to vigorously investigate Kushner.” ([33:16])

5. Political Implications and Public Sentiment

Elections and Republican Worries
- GOP insiders fear loss of the Senate due to war backlash ([36:47]).
- Down-ballot races are feeling the squeeze, with gas prices, agriculture woes, and military family impacts shaping campaign trails ([24:19]).
Military Families and Morale
- Ossoff criticizes Trump for exploiting images of “flag-draped coffins” for fundraising, calling the administration’s attitude toward the military “callous and disgraceful” ([25:48]).

6. Energy Crisis Assessment with Amos Hochstein

Unprecedented Global Energy Crisis
- The current war is depicted as the worst energy crisis the world has ever seen, with oil, natural gas, fertilizer, and supply chains all under threat ([39:58]–[40:55]).
Confusion and Policy Failures
- Hochstein:
  
  “They're coming up with a new plan every day. The bottom line is you’ve got to get out of this conflict because the Strait of Hormuz has to open.” ([41:25])
- Even immediate war cessation won’t end the economic pain:
  
  “Even if tomorrow they announce that we're ending this war... diesel is over $5 so it will take some time even if they end it today. But it doesn't look like they're going to end it tomorrow.” ([43:25])

Notable Quotes and Memorable Moments

On Trump’s Narrative:

"It's not a quagmire because I'm telling you it's not a quagmire... There's not defensive at all." – Rachel Maddow ([05:23])
On Grift:

“This is corruption. This is the most corrupt administration.” – Rep. Robert Garcia on Jared Kushner ([33:16])
On Impacted Americans:

“Just please think about the people, man, what are we really doing there besides raising our prices?” – Florida fisherman ([12:23])
On Lack of Oversight:

"I have decided that we will not have public hearings because I do not believe the administration's decision makers should be subject to Public questioning by senators." – Senator Tim Kaine quoting Senate Foreign Relations Chair ([09:52])
On Military Disrespect:

“It’s the most callous and disgraceful disregard for the sacrifice that these service members have made. It gives the impression that the president and his team really do just view those who wear the uniform as pawns.” – Sen. Jon Ossoff ([25:48])
On Energy Security:

"We've had a lot of energy crises since OPEC in the 1970s... yet this is the worst energy crisis the world has ever seen." – Amos Hochstein ([39:58])

Important Timestamps

01:00 – Start of substantive discussion; recap of Iran war and Trump administration’s messaging
04:29 – Trump’s shifting account of Israeli attack and US culpability
05:01 – Pete Hegseth attacks media coverage
08:03 – Trump claims total military victory; reality check follows
12:05–12:58 – Interviews with disaffected Trump-supporting fishermen
13:29 – Tulsi Gabbard’s testimony on the war’s legality and her role as DNI
15:12 – Sen. Jon Ossoff interview: war objectives, cost, and authority critiques
20:05 – Ossoff on “Dear Leader problem” in intelligence community
24:19 – Economic pain as political wedge in Georgia race
25:48 – Ossoff slams Trump’s disrespect toward military sacrifices
27:00 – Maddow introduces major new “grift” stories: Lewandowski, Don Jr., Kushner
33:16 – Rep. Garcia details the Congressional investigation into Kushner
39:58 – Maddow and Hochstein: depth of global energy crisis and possible paths forward
43:25 – Hochstein explains why even peace won’t bring immediate relief

Conclusion

This episode delivers a dense, urgent, and critical exploration of two crises—war and corruption—in the Trump administration. Voices from the political, economic, and national security arenas highlight a government under siege by its own lack of transparency and rampant self-dealing. Maddow and her guests alternately dissect, mock, and lament both the administration’s inability to manage the war’s fallout and the sheer scale of alleged personal grift by those in power. Frequent, grounded references to polling, economic indicators, insider accounts, and ongoing congressional investigations make for a detailed, accessible, and damning account for listeners wanting an unvarnished overview of current events.

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Transcript

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Rachel Maddow (1:00)

We've got a ton to get to tonight. As I mentioned. Senator Jon Ossoff, who had quite a moment just yesterday, grilling Tulsi Gabbard for answers on Trump's war in Iran. He's gonna join me here at the table in a moment. And there is a lot to talk about because it's now been almost three weeks since Trump launched his war of choice in Iran. Almost three weeks. There's still no clear objective, still no end in sight, still no clear explanation of why Trump started this war in the very first place. But Trump and his cabinet do seem to have finally coalesced, at least for the moment, around a strategy for this war and how they communicate publicly. And that strategy seems to be this. Just wake up every single day and gaslight the American people, tell them everything is going great. Fake it till you make it of sorts. Bully and threaten if necessary. But no matter what, no matter what tactics you use to get there, just keep gaslighting away. I mean, just listen to the way Donald Trump described the economic impact of his disastrous war earlier today.

Donald Trump (2:04)

Everything was going great. The economy was great, oil prices were very low. And I saw what was happening in Iran and I said, I hate to make this excursion, but we're going to have to do it. And I actually thought the numbers would be worse. I thought that it would go up more than it did. So I wanted to put out that fire. And I said, you know, if I do that, oil prices will go up. The economy will go down a little bit. I thought it would be worse. Much worse, actually. I thought there was a chance it could be much worse. It's not bad.

Rachel Maddow (26:54)

Coming up, our friend May Rachel Maddow wondered this week why a story involving Jared Kushner is not more of a show stopping scandal in our country right now. I think we should all wonder this. Well, it appears Congressman Robert Garcia agrees because today he launched an investigation into what Jared Kushner is up to. And he joins me to talk about it next. So today we got some brand new entries into the competition for biggest alleged grift of the Trump administration. And I guess I should say biggest grift so far. There's time to go, people. Time to go. But truly, today we learned about multiple alleged grifts that could be some of the biggest grifts in American history. Let's just start with Corey Lewandowski, and you may know him as Trump's former campaign manager or as Kristi Noem's alleged secret boyfriend, an allegation they both deny. But officially, Corey Lewandowski's title in the federal government is special government employee. Basically, he had been a de facto chief of staff to Kristi Noem at dhs, and the role was supposedly unpaid. But today, NBC News reported that Lewandowski was, at the very least, trying to use that position to enrich himself. Here's the headline. Some DHS contractors told White House officials they were asked to pay Corey Lewandowski. Now, the big allegation in this piece is about the private prison company Geo Group. It is one of the biggest private prison companies in the country and is a key part of ICE's system of detention centers all across the country. A senior DHS official and three people familiar with the discussion told NBC News that after Trump was elected, during the transition, Lewandowski told the founder of Geo Group that he wanted to, quote, be paid in exchange for protecting and growing Geo Group's DHS contracts. Protecting and growing is doing a lot of work there. Now, those sources said that the founder of GeoGroup declined that offer. Then, months later, Trump was sworn in. Kristi Noem was made Secretary of Homeland Security, and Lewandowski got his, quote, unquote, unpaid special government employee gig. So Lewandowski and the founder of Geo Group had another conversation. Now, two industry sources familiar with the matter told NBC News that in that conversation, the founder of Geo Group offered to put Lewandowski on retainer, basically a recurring consulting fee. But those sources say that wasn't enough for Lewandowski because he wanted to be compensated based on the company's new or renewed contracts with dhs. So basically, as a government employee, employee, he allegedly wanted to make money for giving government business to this company. Now, the founder of GeoGroup declined that deal. And then in the months that followed, the length of two of Geo Group's federal contracts shrank and their detention centers sat idle, even while DHS is spending billions building massive new detention centers all around the country, sometimes giving contracts to very inexperienced companies. Now, I should mention that Lewandowski's spokesperson called it absolutely false that Lewandowski even demand that he ever demanded payment from Geo Group. And DHS's General Counsel's office told NBC News that Lewandowski is in compliance with all required ethics, financial disclosure, reporting and training requirements. Okay, but. Oh, boy. I mean, that is a hell of a story. And that is just one of the stories. Just one about major alleged grift we got today. The other is about President Trump's adult son, John Jr. Last year, Don Jr. S venture capital firm invested in a startup focused on Rare earth magnet production. Three months after that investment, the startups landed a $620 million government contract. How lucky for them, isn't it? Now, while the Rare Earth magnet startup was only valued at about $200 million when Don Jr's firm invested in it today, people familiar with the matter told Bloomberg that the startup is now valued at nearly $2 billion. I should note that all the parties involved told Bloomberg that there was no connection between the Trump administration's decision to back the company and the investment by John Jr's firm. The startup CEO says he has never communicated with Don Jr. In any way. Don Jr. S venture capital firm says it had zero involvement in the government contract. And a spokesperson for Don Jr. Says that he doesn't interface with the federal government on behalf of any company that he invests in or advises. Guess it's just some really, really coincidental good luck, I guess. Now, we got these two new stories today, but amazingly, they don't even come close to the scale of the biggest alleged corruption story we got this week. A scandal that is all the more concerning now that the United States is at war with Iran, because on Friday, the New York Times reported that Jared Kushner is still soliciting funds from countries in the Middle east while actively negotiating on America's behalf as Trump's Middle east envoy. No conflict of interest there, is there? I mean, there's an obvious one. Five people with knowledge of the talks told the New York Times that Kushner had spoken to potential investors about raising another $5 billion for his investment firm. Two people briefed on the discussions told the Times that Kushner's firm has already met with the Saudi Arabian Public Investment Fund and that other sovereign wealth funds from countries like the UAE and Qatar are also expected to be asked for more. Now, the chief legal officer for Kushner's investment fund told the Times that the firm does not intend to take any additional capital while Jared is volunteering for the government. And a spokesperson for the White House said the Kushner only acts in the best interest of the American people, however they define that. I don't know about you, but I would like someone to double check all of that. And thankfully, Democrats in Congress are on the case. One of the Democrats leading that charge, the ranking member of the House Oversight Committee, Robert Garcia, joins me now. Okay. One of our amazing producers, Sam, put that all together. We may have missed some things. There were so many details, but UN Sen. Wyden sent two letters today. One demanding answers from Kushner's investment firm about what they have been doing. The other demanding answers from the White House about what exactly Jared has been doing on behalf of. Of the US Government. Give us the specifics of what information you are looking for, what you want from them.