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Supreme Court

After 20 Years as Chief Justice, John Roberts Is Now Friend and Foe to Executive Power

Which version of the chief justice will emerge in the Supreme Court’s newest term?

Damon Root | 10.2.2025 7:00 AM

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A black and white image of John Roberts in the foreground and the United States Supreme Court building in the background | Illustration: Eddie Marshall | BONNIE CASH | UPI | Newscom | Midjourney
(Illustration: Eddie Marshall | BONNIE CASH | UPI | Newscom | Midjourney)

It has now been just a little over 20 years since John Roberts was sworn in as chief justice of the United States back on September 29, 2005. So let's mark this two-decade milestone by taking a closer look at Roberts' jurisprudence and the mark it has left on American law, especially when it comes to the powers of the president.

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Characterizing Roberts' judicial philosophy is no simple task. Is it accurate to say that he practices judicial restraint by deferring to the policy choices made by elected officials? Yes, we can accurately say that, but only sometimes.

In one of his most famous majority opinions, Roberts led the Supreme Court in upholding the Patient Protection and Affordable Care Act, also known as Obamacare. "It is not our job," Roberts declared in National Federation of Independent Business v. Sebelius (2012), "to protect the people from the consequences of their political choices." In other words, the argument went, because Obamacare represented the will of the people as expressed via the agenda of a popularly elected president, the unelected judiciary had no business standing in the way.

Yet Roberts has also led the Supreme Court in thwarting the agendas of popularly elected presidents in other high-profile cases. In Department of Homeland Security v. Regents of the University of California (2020), Roberts wrote the majority opinion stopping President Donald Trump from rescinding the Deferred Action for Childhood Arrivals (DACA) program. In Biden v. Nebraska (2023), Roberts blocked President Joe Biden from imposing his student debt cancellation plan. No deference for either president in those important cases.

But Roberts has also led the Supreme Court in massively expanding executive power, most notably in Trump v. United States (2024), which granted the president broad immunity from criminal prosecution.

So, while both Biden and Trump saw some of their signature presidential policies struck down, the signature policy of President Barack Obama was upheld on deferential grounds, and the presidency itself has emerged stronger than ever in other crucial ways, all thanks to decisions written by Roberts.

Is there a through line connecting such cases? Is there a clear judicial philosophy that accounts for the results? I've been following Roberts's tenure for much of the last two decades, and I'm not sure that there is. Roberts has long extolled the virtues of judicial deference, yet he only does the deferring in select cases. Roberts has put a stop to presidential overreach (sometimes), yet he has also placed a vast protective shield over presidential misconduct. To be generous, I suppose we might say that Roberts's judicial philosophy contains multitudes.

Next week, the Supreme Court will kick off its 2025–2026 term, and the docket is already packed with momentous cases dealing with the powers of the president. That means that all eyes will be on the chief justice, who may well be in the position to tip the balance in one or more of these matters.

Will we get the version of Roberts that's more likely to defer to Trump or the one that's more likely to curtail Trump? Which one of Roberts's judicial multitudes will step to the fore?

For better or worse, we're about to find out.

Start your day with Reason. Get a daily brief of the most important stories and trends every weekday morning when you subscribe to Reason Roundup.

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NEXT: Brickbat: Head in the Sand

Damon Root is a senior editor at Reason and the author of A Glorious Liberty: Frederick Douglass and the Fight for an Antislavery Constitution (Potomac Books). His next book, Emancipation War: The Fall of Slavery and the Coming of the Thirteenth Amendment (Potomac Books), will be published in June 2026.

Supreme CourtExecutive PowerJohn RobertsDonald TrumpTrump AdministrationJudiciaryImmigration
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  1. Leo Kovalensky II   2 months ago

    Roberts should never be forgiven for his opinions in creating a "penaltax" out of thin air to support a massive government expansion and the expansion of executive powers in Trump V US.

    Is it accurate to say that he practices judicial restraint by deferring to the policy choices made by elected officials? Yes, we can accurately say that, but only sometimes.

    It seems more accurate to say only when those policies align with his own policy preferences; the Constitution be damned.

    1. Wizzle Bizzle   2 months ago

      Indeed. After destroying conservatism, Bush Jr left us with this peach to remind us what a terrible president he was.

      It is common knowledge in DC that Roberts made his ACA ruling in response to a media pressure campaign, which makes him unfit to be a judge. He has only come around to "hard" decisions because his vote generally doesn't matter anymore. He just votes the way the majority is going so he doesn't get left off of the winning team. He's a true politician.

      1. JesseAz (RIP CK)   2 months ago

        When he is outvoted he joins the majority and appoints himself the writer to give the least available ruling against an overturned precedent.

    2. Neutral not Neutered   2 months ago

      If you are President, we know not possible, would it be proper for you to be able to make decisions without being sued for them?

      Consider the alternative had Trump not won?

      What the democrat did was abhorrent enough but to have actually made it a legal precedent to sue the President for performing his duties simply because you disagree politically would have destroyed America with one ruling.

      Think a bit deeper if it is possible.

  2. Chumby   2 months ago

    A result of team sarcles’ kayaktifa intimidation?

  3. I, Woodchipper   2 months ago

    Never forget the penaltax. This man is a fraud.

  4. Sometimes a Great Notion   2 months ago

    7000+ days too long.

  5. Rossami   2 months ago

    One hypothesis is that Roberts is waffling on the issue of presidential power. An alternative hypothesis (and one I think is far more likely) is that Roberts is consistent but on a factor other than presidential power.

    Consider an analogy. I am observed driving - sometimes at 25 mph, sometimes at 65 mph. One view is that I waffle in my driving speed. An alternative view is that I am consistent in complying with the posted speed limits and it's that external factor that drives the variance in my decisions.

  6. TJJ2000   2 months ago

    Oh FFS ... "Will we get the version of Roberts that's more likely to defer to Trump or the one that's more likely to curtail Trump?"

    Only to the TDS-Leftarded does the whole F'En USA revolve around Anti-Trump or Pro-Trump (WHO). Because that's the very foundation of [WE] *Identify-as* RULES 'democracy' ONLY.

    How about an article summary about how Supreme Court Justices have honored the U.S. Constitution (WHAT) not (WHO)? And having the cognitive ability to think outside of 'gangster' mentality and more inline with some honor-ability to a *Constitutional* Republic NOT just a gangster-rules democracy.

    It's like the Democrat mind will never think long enough to understand anything beyond their 'gangster' RULES mentality. So their one-track mind has no other choice but to Self-Project that 'gangster' mentality onto everyone else.

  7. JohannesDinkle   2 months ago

    Another issue is that, if the executive branch is not entirely under the control of an elected President, then who is in charge - unelected bureaucrats? If the issue is clear, say a law passed by Congress stating clearly that appointments are for life, then the President is stuck. If it is merely assumed that, once appointed or hired by one President they may not be fired by another, then Trump has room to move.

  8. MWAocdoc   2 months ago

    In no way is Roberts any kind of mixture. Judicial deference only applies to Congressional actions and then only when the laws they pass are within Constitutional limits and not unconstitutionally broad and vague. Judicial deference NEVER applies to Executive branch actions. Saying that Roberts’ opinions sometimes thwart Presidential aspirations understates the malfeasance in office greatly! He only thwarts Presidential actions when he doesn’t like them because they don’t fit in his social “legislation from the bench” agenda. Full stop.

  9. Dillinger   2 months ago

    >>Characterizing Roberts' judicial philosophy is no simple task.

    What result does the Ruling Class seek?

    1. MWAocdoc   2 months ago

      And yet I had no problem characterizing it. Damon seemed to struggle with categorizing apples and oranges when he tried to lump them all into the same basket he labeled "fruit." All of Roberts' opinions fit neatly into the "living document" nanny state authoritarian basket, referring to the Constitution only as needed to pervert its original intent in order to arrive at a painfully contorted desired outcome.

  10. Uomo Del Ghiaccio   2 months ago

    Chief Justice John Roberts is more concerned about his legacy than he is about justice and clear and precise laws. Instead of clarity, he fosters fuzziness and contradictory troublesome rulings. He pays more attention to the opinions of the media talking heads, than logically interpreting the conflicts that arise within law.

    The Judicial Branch under Chief Justice John Roberts is at best a mixed bag. It's like he sticks his fingers into the air to see what direction the wind is blowing, but instead of listening to the actual people, he listens to the detached legacy media talking heads who purposely distort and propagandize against the will of the people.

    Chief Justice John Roberts is a stooge of the machine listening to the dying legacy media attempting to perpetuate the power of the ruling elitists and keep the populace in there subservient places.

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