Is Donald Trump the Slim Shady of Tax Returns?

October 03, 2016

Writer

How would you handle a $916 million financial loss? If you're anything like Donald Trump, you'd use the tax code to ease the burden.

The New York Times published three pages of the presidential candidate's 1995 tax returns, but was there a smoking gun?

"From what I know . . . it is not shady. It is standard practice in law, especially in business with tax law," Glenn said Monday on his radio program.

So is there anything that could be shady about avoiding taxes for more than 15 years --- or does that make Trump really smart?

Read below or watch the clip for answers to these tax-free questions:

• Should you take advantage of an available tax break?

• What's our moral obligation?

• Did Donald Trump do anything illegal?

• What's dangerous about Donald Trump's tax returns?

• If anything is shady about Trump's returns, is it still okay to celebrate?

Below is a rush transcript of this segment, it might contain errors:

GLENN: All right. So I want -- so I want to talk to you about Donald Trump's taxes. And in case -- in case you missed it, for what we know right now, there's -- nobody's claiming that he did anything illegal. It is a feature in the tax system. And if that's available to you, you should take it. It's not shady.

PAT: And what that is, is, he potentially didn't pay taxes for 18 or 20 years. But that's because he had a massive --

GLENN: I don't think you can do it that long. For fifteen years?

PAT: A massive write-down.

GLENN: Fifteen years?

STU: Fifteen into the future and three into the past.

PAT: So it's 18 years?

STU: But, again, they have no evidence to support that, other than the fact that he took a loss in one year. He may have taken losses in every other year too. We have no idea.

GLENN: Right. But you would take that. I mean, if you had a loss that big, you would take it.

PAT: You would. If you lost almost a billion dollars.

GLENN: Yeah, you would take that. Of course you would. And that's normal, rational. And everybody who would be in that situation would take it.

PAT: Yeah.

STU: Right. They're trying to say, well, it was immoral for him -- he just should have started paying taxes. No.

GLENN: No, it's not. If you sell your house and you have to sell your house at a massive and then you have a good year the next year, then you should take that massive loss and use it against it against the next year. Because you just lost all that money.

STU: Right. And there might be a moral -- and I think there is -- a moral reason to help people. That does not mean there's a moral reason to pay taxes into a system where they're going to waste it constantly. You have to follow the law.

PAT: There is a moral reason to help people. But it has nothing to do with taxation anyway. You don't give it to the government to give it to somebody. You give it to somebody. That's your moral obligation.

GLENN: Right. So here's the problem with this, because this is being interpreted by many as kind of shady, on both sides. Okay? Shady.

A, from what I know about it, it is not shady. It is standard practice in law, especially in business, with tax law.

STU: Real estate.

GLENN: Right. And real estate. It is standard practice. So it's not shady at all. But people are -- people -- some people -- supporters are celebrating this, thinking that even if it is shady, he's smart. That's dangerous.

The -- the celebration behind it, if you think it's shady, is dangerous. Because this is the beginning of burn the entire system down. This is the beginning of, if -- if I can get away with it, I'm going to.

That's not who we are. That's not who we are. We should not be the kind of people of, "If I can get away with it, I'll do it." Jeffy, say nothing.

We are -- we are -- as a nation, should not be celebrating that kind of attitude. But that's not -- that's not the case here. This is not shady.

PAT: Especially since those same people would be saying we're a nation of laws, and that's why we've got to uphold the border laws. Well, the same thing applies to taxes. We're a nation of laws.

GLENN: Yes. Right. If he did something shady, which is not even being thrown his way, he should pay the penalty. And he should not celebrate that as being smart. But this was not shady, as far as we know.

Featured Image: US Republican presidential nominee Donald Trump visits the Gerald Ford Presidential Museum in Grand Rapids, Michigan, on September 30, 2016. (Photo Credit: JEWEL SAMAD/AFP/Getty Images)

The Woodrow Wilson strategy to get out of Mother’s Day

Stock Montage / Contributor, Xinhua News Agency / Contributor | Getty Images

I’ve got a potentially helpful revelation that’s gonna blow the lid off your plans for this Sunday. It’s Mother’s Day.

Yeah, that sacred day where you’re guilt-tripped into buying flowers, braving crowded brunch buffets, and pretending you didn’t forget to mail the card. But what if I told you… you don’t have to do it? That’s right, there’s a loophole, a get-out-of-Mother’s-Day-free card, and it’s stamped with the name of none other than… Woodrow Wilson (I hate that guy).

Back in 1914, ol’ Woody Wilson signed a proclamation that officially made Mother’s Day a national holiday. Second Sunday in May, every year. He said it was a day to “publicly express our love and reverence for the mothers of our country.” Sounds sweet, right? Until you peel back the curtain.

See, Wilson wasn’t some sentimental guy sitting around knitting doilies for his mom. No, no, no. This was a calculated move.

The idea for Mother’s Day had been floating around for decades, pushed by influential voices like Julia Ward Howe. By 1911, states were jumping on the bandwagon, but it took Wilson to make it federal. Why? Because he was a master of optics. This guy loved big, symbolic gestures to distract from the real stuff he was up to, like, oh, I don’t know, reshaping the entire federal government!

So here’s the deal: if you’re looking for an excuse to skip Mother’s Day, just lean into this. Say, “Sorry, Mom, I’m not celebrating a holiday cooked up by Woodrow Wilson!” I mean, think about it – this is the guy who gave us the Federal Reserve, the income tax, and don’t even get me started on his assault on basic liberties during World War I. You wanna trust THAT guy with your Sunday plans? I don’t think so! You tell your mom, “Look, I love you, but I’m not observing a Progressive holiday. I’m keeping my brunch money in protest.”

Now, I know what you might be thinking.

“Glenn, my mom’s gonna kill me if I try this.” Fair point. Moms can be scary. But hear me out: you can spin this. Tell her you’re honoring her EVERY DAY instead of some government-mandated holiday. You don’t need Wilson’s permission to love your mom! You can bake her a cake in June, call her in July, or, here’s a wild idea, visit her WITHOUT a Woodrow Wilson federal proclamation guilting you into it.

Shocking Christian massacres unveiled

Aldara Zarraoa / Contributor | Getty Images

Is a Christian Genocide unfolding overseas?

Recent reports suggest an alarming escalation in violence against Christians, raising questions about whether these acts constitute genocide under international law. Recently, Glenn hosted former U.S. Army Special Forces Sniper Tim Kennedy, who discussed a predictive model that forecasts a surge in global Christian persecution for the summer of 2025.

From Africa to Asia and the Middle East, extreme actions—some described as genocidal—have intensified over the past year. Over 380 million Christians worldwide face high levels of persecution, a number that continues to climb. With rising international concern, the United Nations and human rights groups are urging protective measures by the global community. Is a Christian genocide being waged in the far corners of the globe? Where are they taking place, and what is being done?

India: Hindu Extremist Violence Escalates

Yawar Nazir / Contributor | Getty Images

In India, attacks on Christians have surged as Hindu extremist groups gain influence within the country. In February 2025, Hindu nationalist leader Aadesh Soni organized a 50,000-person rally in Chhattisgarh, where he called for the rape and murder of all Christians in nearby villages and demanded the execution of Christian leaders to erase Christianity. Other incidents include forced conversions, such as a June 2024 attack in Chhattisgarh, where a Hindu mob gave Christian families a 10-day ultimatum to convert to Hinduism. In December 2024, a Christian man in Uttar Pradesh was attacked, forcibly converted, and paraded while the mob chanted "Death to Jesus."

The United States Commission on International Religious Freedom (USCIRF) recommends designating India a "Country of Particular Concern" and imposing targeted sanctions on those perpetrating these attacks. The international community is increasingly alarmed by the rising tide of religious violence in India.

Syria: Sectarian Violence Post-Regime Change

LOUAI BESHARA / Contributor | Getty Images

Following the collapse of the Assad regime in December 2024, Syria has seen a wave of sectarian violence targeting religious minorities, including Christians, with over 1,000 killed in early 2025. It remains unclear whether Christians are deliberately targeted or caught in broader conflicts, but many fear persecution by the new regime or extremist groups. Hayat Tahrir al-Sham (HTS), a dominant rebel group and known al-Qaeda splinter group now in power, is known for anti-Christian sentiments, heightening fears of increased persecution.

Christians, especially converts from Islam, face severe risks in the unstable post-regime environment. The international community is calling for humanitarian aid and protection for Syria’s vulnerable minority communities.

Democratic Republic of Congo: A "Silent Genocide"

Hugh Kinsella Cunningham / Stringer | Getty Images

In February 2025, the Allied Democratic Forces (ADF), an ISIS-affiliated group, beheaded 70 Christians—men, women, and children—in a Protestant church in North Kivu, Democratic Republic of Congo, after tying their hands. This horrific massacre, described as a "silent genocide" reminiscent of the 1994 Rwandan genocide, has shocked the global community.

Since 1996, the ADF and other militias have killed over six million people, with Christians frequently targeted. A Christmas 2024 attack killed 46, further decimating churches in the region. With violence escalating, humanitarian organizations are urging immediate international intervention to address the crisis.

POLL: Starbase exposed: Musk’s vision or corporate takeover?

MIGUEL J. RODRIGUEZ CARRILLO / Contributor | Getty Images

Is Starbase the future of innovation or a step too far?

Elon Musk’s ambitious Starbase project in South Texas is reshaping Boca Chica into a cutting-edge hub for SpaceX’s Starship program, promising thousands of jobs and a leap toward Mars colonization. Supporters see Musk as a visionary, driving economic growth and innovation in a historically underserved region. However, local critics, including Brownsville residents and activists, argue that SpaceX’s presence raises rents, restricts beach access, and threatens environmental harm, with Starbase’s potential incorporation as a city sparking fears of unchecked corporate control. As pro-Musk advocates clash with anti-Musk skeptics, will Starbase unite the community or deepen the divide?

Let us know what you think in the poll below:

Is Starbase’s development a big win for South Texas?

Should Starbase become its own city?

Is Elon Musk’s vision more of a benefit than a burden for the region?

Shocking truth behind Trump-Zelenskyy mineral deal unveiled

Chip Somodevilla / Staff | Getty Images

President Donald Trump and Ukrainian President Volodymyr Zelenskyy have finalized a landmark agreement that will shape the future of U.S.-Ukraine relations. The agreement focuses on mineral access and war recovery.

After a tense March meeting, Trump and Zelenskyy signed a deal on Wednesday, April 30, 2025, granting the U.S. preferential mineral rights in Ukraine in exchange for continued military support. Glenn analyzed an earlier version of the agreement in March, when Zelenskyy rejected it, highlighting its potential benefits for America, Ukraine, and Europe. Glenn praised the deal’s strategic alignment with U.S. interests, including reducing reliance on China for critical minerals and fostering regional peace.

However, the agreement signed this week differs from the March proposal Glenn praised. Negotiations led to significant revisions, reflecting compromises on both sides. What changes were made? What did each leader seek, and what did they achieve? How will this deal impact the future of U.S.-Ukraine relations and global geopolitics? Below, we break down the key aspects of the agreement.

What did Trump want?

Bloomberg / Contributor | Getty Images

Trump aimed to curb what many perceive as Ukraine’s overreliance on U.S. aid while securing strategic advantages for America. His primary goals included obtaining reimbursement for the billions in military aid provided to Ukraine, gaining exclusive access to Ukraine’s valuable minerals (such as titanium, uranium, and lithium), and reducing Western dependence on China for critical resources. These minerals are essential for aerospace, energy, and technology sectors, and Trump saw their acquisition as a way to bolster U.S. national security and economic competitiveness. Additionally, he sought to advance peace talks to end the Russia-Ukraine war, positioning the U.S. as a key mediator.

Ultimately, Trump secured preferential—but not exclusive—rights to extract Ukraine’s minerals through the United States-Ukraine Reconstruction Investment Fund, as outlined in the agreement. The U.S. will not receive reimbursement for past aid, but future military contributions will count toward the joint fund, designed to support Ukraine’s post-war recovery. Zelenskyy’s commitment to peace negotiations under U.S. leadership aligns with Trump’s goal of resolving the conflict, giving him leverage in discussions with Russia.

These outcomes partially meet Trump’s objectives. The preferential mineral rights strengthen U.S. access to critical resources, but the lack of exclusivity and reimbursement limits the deal’s financial benefits. The peace commitment, however, positions Trump as a central figure in shaping the war’s resolution, potentially enhancing his diplomatic influence.

What did Zelenskyy want?

Global Images Ukraine / Contributor | Getty Images

Zelenskyy sought to sustain U.S. military and economic support without the burden of repaying past aid, which has been critical for Ukraine’s defense against Russia. He also prioritized reconstruction funds to rebuild Ukraine’s war-torn economy and infrastructure. Security guarantees from the U.S. to deter future Russian aggression were a key demand, though controversial, as they risked entangling America in long-term commitments. Additionally, Zelenskyy aimed to retain control over Ukraine’s mineral wealth to safeguard national sovereignty and align with the country’s European Union membership aspirations.

The final deal delivered several of Zelenskyy’s priorities. The reconstruction fund, supported by future U.S. aid, provides a financial lifeline for Ukraine’s recovery without requiring repayment of past assistance. Ukraine retained ownership of its subsoil and decision-making authority over mineral extraction, granting only preferential access to the U.S. However, Zelenskyy conceded on security guarantees, a significant compromise, and agreed to pursue peace talks under Trump’s leadership, which may involve territorial or political concessions to Russia.

Zelenskyy’s outcomes reflect a delicate balance. The reconstruction fund and retained mineral control bolster Ukraine’s economic and sovereign interests, but the absence of security guarantees and pressure to negotiate peace could strain domestic support and challenge Ukraine’s long-term stability.

What does this mean for the future?

Handout / Handout | Getty Images

While Trump didn’t secure all his demands, the deal advances several of his broader strategic goals. By gaining access to Ukraine’s mineral riches, the U.S. undermines China’s dominance over critical elements like lithium and graphite, essential for technology and energy industries. This shift reduces American and European dependence on Chinese supply chains, strengthening Western industrial and tech sectors. Most significantly, the agreement marks a pivotal step toward peace in Europe. Ending the Russia-Ukraine war, which has claimed thousands of lives, is a top priority for Trump, and Zelenskyy’s commitment to U.S.-led peace talks enhances Trump’s leverage in negotiations with Russia. Notably, the deal avoids binding U.S. commitments to Ukraine’s long-term defense, preserving flexibility for future administrations.

The deal’s broader implications align with the vision Glenn outlined in March, when he praised its potential to benefit America, Ukraine, and Europe by securing resources and creating peace. While the final agreement differs from Glenn's hopes, it still achieves key goals he outlined.

Glenn's Show Prep