June 21, 2026

MM#485--The Umpire Who Joined The Game

FAN MAIL--We would love YOUR feedback--Send us a Text Message He told America judges are umpires, not lawmakers. Two decades later, Chief Justice John Roberts is still calling balls and strikes, but sometimes it sounds like he’s redrawing the strike zone. We dig into the irony and the real-world consequences of Roberts’ “institutionalist” approach, starting with one of the most debated Supreme Court decisions of our time: the Obamacare individual mandate in *NFIB v. Sebelius*. We walk throug...

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FAN MAIL--We would love YOUR feedback--Send us a Text Message

He told America judges are umpires, not lawmakers. Two decades later, Chief Justice John Roberts is still calling balls and strikes, but sometimes it sounds like he’s redrawing the strike zone.

We dig into the irony and the real-world consequences of Roberts’ “institutionalist” approach, starting with one of the most debated Supreme Court decisions of our time: the Obamacare individual mandate in *NFIB v. Sebelius*. We walk through why conservatives thought the Commerce Clause argument was clean, why Roberts initially seemed to agree, and how the case turned on a single reframe: treating the penalty as a tax under Congress’ taxing power. That move didn’t just keep a law alive, it reshaped how many people trust the Court.

Then we hold that up against Molly Hemingway’s portrait of Justice Samuel Alito, a justice known less for smoothing edges and more for saying what he thinks, even when it’s uncomfortable. From the Citizens United State of the Union moment to Alito’s willingness to let dissents stand on the record, we explore what “courage” looks like on a bench that is always being read through a partisan lens.

Finally, we connect the same tension to a live controversy over birthright citizenship in Trump versus Barbara, the Fourteenth Amendment, and *Wong Kim Ark*. When Roberts fires back, “it might be a new world, but it’s certainly the same Constitution,” we ask what consistency really demands.


Key Points from the Episode:


• Roberts’ confirmation-hearing metaphor and the legitimacy problem
• How the Roberts Court moves law right while Roberts surprises conservatives
• The Obamacare individual mandate and the “penalty as a tax” reasoning
• Molly Hemingway’s portrait of Alito as the road not taken
• Alito’s “not true” reaction to Obama after Citizens United
• Trump versus Barbara and the Fourteenth Amendment debate over birthright citizenship
• What “same Constitution” means when the stakes are political


Links

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Substack https://mojoacademy.substack.com/

🎙️ Theory 2 Action podcast 👇

Website and other great resources https://www.teammojoacademy.com/

🎥 Youtube Channel 👇

MOJO Academy on Youtube : click here




00:07 - Welcome And Today’s Mojo Minute

01:02 - Roberts And The Umpire Promise

03:22 - The Obamacare Mandate Flip

05:35 - Hemingway’s Alito And Holding The Line

06:27 - Alito’s Citizens United Moment

08:33 - Institutionalism Versus Plain Text

08:59 - Birthright Citizenship And The 14th

10:43 - Same Constitution And The Irony

11:39 - Book Recommendation And Closing

Welcome And Today’s Mojo Minute

SPEAKER_00

Welcome to the Theory to Action Podcast, where we examine the timeless treasures of wisdom from the great books in less time to help you take action immediately and ultimately to create and lead a flourishing life. Now, here's your host, David Kaiser.

SPEAKER_01

Hello, I am David, and welcome back to another Mojo Minute. Recently, I just finished reading Molly Hemingway's incredible book, Alito, the Justice Who Reshaped the Supreme Court and restored the Constitution. And I just have to say the irony between Chief Justice John Roberts and Justice Samuel Leto's jurisprudence, you know how they roll from the in terms of their legalese and what they write. Boy, it is quite telling.

Roberts And The Umpire Promise

SPEAKER_01

You see, John Roberts, by his account, did not want to be part of the story. You know, back in 2005, at his confirmation hearing, he gave all of us a simple promise. Judges are like umpires, he said. They don't make rules. You can envision just call balls and strikes, no agenda, no politics, just the game. Call it fairly. It's a great line. It's modest, humble, careful. Exactly what you'd want a chief justice to sound like. But 20 years later, you almost have to smile reading that back because John Roberts hasn't just called balls and strikes. He has become, at different moments, both the most important conservative on the court, if you can call him that, and the man conservatives trust least. It's not a contradiction, by the way, it's the whole story. And that's what I want to share today. When George W. Bush appointed him to replace Chief Justice Rehnquist, William Rehnquist, you got exactly what conservatives at the time wanted. Sharp, careful, deeply credentialed, allergic to drama. Certainly someone who could get past the Senate confirmation hearing. Now, over two decades, the court bearing his name has moved the country's law meaningfully to the right. Campaign finance reform, voting rights, reigning in the federal agencies. The Roberts court earned that name for a reason. But there's also a second instinct running underneath the first one. Roberts has never wanted the court to look like nine politicians in robes. He has said as much, and he has said it more than once. And that instinct of his to protect the institution, to protect its legitimacy, don't let it look like partisan even when the outcomes are split exactly the way you would expect them to be, split, especially along partisan lines, has occasionally pulled him somewhere. Certainly conservatives didn't see coming.

The Obamacare Mandate Flip

SPEAKER_01

That year the court took up the individual mandate at the heart of Obamacare, the requirement that you have to buy health insurance or pay a penalty. Conservatives had an extremely clean argument. It was argued well, the law was tight, good legalese, well written, clear, concise. Congress can't use the Commerce Clause to force you into a market you never chose to enter. And Chief Justice Roberts initially agreed. He said so in writing. And then he went on to save the law anyway. He did it by re-characterizing the penalty. He said it was not a mandate enforced through the commerce power, but it was a tax. And taxes, Roberts wrote, are squarely within the Congress's constitutional authority. The mandate, quote, may reasonably be characterized as a tax, he wrote. And because the Constitution permits that kind of tax, it wasn't the court's job to question its wisdom. And here's what made all of that sting. The Obama administration had spent the entire legislative fight telling you and me repeatedly that this was not a tax. Politically toxic to admit otherwise. So Roberts did what the law's own authors refused to do. And he used it to keep the law standing. You can certainly imagine how conservatives took that. Not as craftsmanship, not as a good justice keeping together a slight majority, but it was certainly a flip. Reporting afterwards suggested Roberts may have initially sided with striking down the mandate and then switched late in the process. Whatever actually happened behind the closed doors, you got the same result either way. The law conservatives wanted gone, stayed exactly where it was. Kept alive by the one vote nobody saw coming.

Hemingway’s Alito And Holding The Line

SPEAKER_01

So again, I just finished reading Molly Hemingway's incredible new book, Alito, the Justice Who Reshaped, helped reshape the Supreme Court and restore the Constitution. And when you read that book, you can't help but see the Obamacare decision a little bit differently. Once you sat with her account of that era. Her portrait of Alito is in part a portrait of the road Roberts did not take. The justice sitting right next to him, who did not bend. Where Roberts moved to protect the court's standing, you know the institutionalist. Alito's courage and instinct ran the other way. Hold the line on the text. Let the chips fall where they may. And you already know Alito isn't great at hiding what he thinks.

Alito’s Citizens United Moment

SPEAKER_01

You got to go back to January 2010 in Obama's State of the Union. The president stood up and told the country the court had just reversed a century of law with the Citizens United decision. Alito sitting right there in the front row with the rest of the justices shook his head. His body language clearly evident, and he mouthed the two words, not true. No microphone, no statement, just a sitting Supreme Court justice live on national television, openly disagreeing with the President of the United States to his face. Thank you, Judge Alito. And he didn't go back the next year. He later said it was hard to keep a poker face in that room, which, if he had seen the tape, you already knew. But that's the temperament you're dealing with in Judge Alito. So picture him just two years later watching Roberts in 2012. The man who promised America to be an umpire had just invented an entire category for the call, not balls and strikes, a whole new part of the strike zone. Conjured on the spot from the bench because the alternative felt too, well, disruptive, I guess is what Roberts would say. If Alito couldn't keep his face still over campaign finance reform in the line from Obama, he disagreed with. Imagine what it took for him to sit silently through that one. He didn't say it out loud at the time. He wrote the dissent instead and let the record carry it for itself. The contrast is where the label comes in. The one that followed Roberts ever since. Roberts the institutionalist. Robert's the man who will bend the doctrine if the alternative looks too much like the court's picking a side. Alito, the man who will have the courage to tell you exactly what he thinks. Mouth shut or not. Which brings us, you and me, to right now.

Institutionalism Versus Plain Text

SPEAKER_01

A case that might be testing the very same instinct again. Just pointed all of us somewhere else entirely. Trump versus Barbara is asking whether a president can use an executive order to redefine birthright citizenship, requiring proof of a parent citizenship or legal residency before a child born on U.S. soil counts

Birthright Citizenship And The 14th

SPEAKER_01

as an American citizen. It's a direct challenge to the language that sat in the 14th Amendment since 1868. And the case Juan Kim Ark, the 1898 case, that has anchored birthright citizenship for well over a century. Now, at oral argument, not to get in the weeds, but at oral argument this spring, you had the administration's lawyer leaning on a handful of narrow, long-recognized exceptions. Children of foreign diplomats, children of invading soldiers trying to sketch them to cover a much broader group. And actually, I think he was probably right. Don't think the first 14th Amendment ever allowed for, certainly wasn't written for birthright citizenship. It was written to protect and to give African Americans, former slaves, the right to citizenship. But the administration made the case, and Roberts wasn't buying any of it. He called the reasoning quirky when the lawyer pivoted to modern problems after that, birthright tourism, and the world the framers never could have imagined, and certainly the world that the Fourteenth Amendment was written in, Roberts gave him a line back that said this. Well, it might be a new world, but it's certainly the same Constitution. And that's that's a great line. It was reported all the time. It was reported everywhere. That kind of line you want the umpire

Same Constitution And The Irony

SPEAKER_01

to say, who actually believes in his own metaphor. But boy, if you were sitting there with Judge Alito right next to him, you'd be forgiven for hearing something sharper underneath it. Something closer to just Justice Roberts? Same constitution? You say it's a new world, but it's the same constitution. You were the one who reached past the text and called a penalty attacks to save a law you didn't even agree with. And now you want credit for holding the line? Holy smokes the irony. Alito's restraint here isn't the absence of a reaction, it's the discipline. It's the same discipline that every so often still loses to a man who once looked at a sitting president in the eye and just could not help himself.

Book Recommendation And Closing

SPEAKER_01

May God bless Samuel Alito. May you check out Molly Hemingway's new book, It's Fantastic. And perhaps John Roberts can go back to being the umpire he promised to be and not become part of the story. Just perhaps. As always, keep fighting the good fight.

SPEAKER_00

Thank you for joining us. We hope you enjoyed this theory to action podcast. Be sure to check out our show page at teammojocademy.com, where we have everything we discussed in this podcast as well as other great resources. Until next time, keep getting your emojoy.