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I've just read this article on Slate. In it, they describe how Trump's administration has ignored deadlines imposed by the U.S. District Court after losing a case to SCOTUS (I bolded the most relevant specific example).

The Trump administration announced on Tuesday that it will continue to defy a federal court order compelling the full restoration of DACA, the Obama-era program that allows 700,000 immigrants to live and work in the United States legally. By doing so, the administration has chosen to flout a decision by the Supreme Court, effectively rejecting the judiciary’s authority to say what the law is.

Donald Trump first attempted to rescind the Deferred Action for Childhood Arrivals program in September 2017, a move that would’ve stripped its beneficiaries of work permits and subjected them to deportation. But his administration continually cut corners, failing to explain the basis for its decision and refusing to consider the impact of DACA repeal on immigrants, their communities, and their employers (including the U.S. Army). This June, the Supreme Court ruled that the administration’s actions were “arbitrary and capricious” under federal law and therefore “set aside” DACA repeal.

To implement that decision, U.S. District Judge Paul Grimm compelled the administration to restore DACA to its pre-repeal condition on July 17. Grimm’s order required the Department of Homeland Security to let DACA beneficiaries renew their status for two years, accept new applicants, and restore “advance parole,” which permits travel outside the country. But DHS did not do that. Instead, the agency maintained that it would reject new DACA applicants. It also declined to accept DACA renewals or reinstate advance parole.

Does SCOTUS and the judicial branch have any way to actually enforce laws on the executive branch? It's one thing to enforce laws on some random citizen, but it seems there is no way for SCOTUS to enforce laws against the branch of government that's responsible for enforcing laws.

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    "John Marshall has made his decision, now let him enforce it." ---attributed to Andrew Jackson. Jul 29 '20 at 1:49
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    "It's one thing to enforce laws on some random citizen" - Is it? They can't even do that by themselves. They need the executive branch (i.e. the police or US marshal or someone with a gun) to really enforce anything if it comes down to resisting.
    – Doug
    Jul 29 '20 at 2:15
  • @Doug All I meant by that is, the executive branch has no direct conflict of interest with enforcing laws on a random citizen, so there's little reason for them to disobey SCOTUS there.
    – spacetyper
    Jul 29 '20 at 2:16
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The US courts (including the US Supreme Court) do not have an army or even a police force under their direct control, except for a few court bailiffs. Ultimately, if the executive simply defies the courts, the only remedy is a political one.

A court can order a person held unlawfully to be released from detention, but the jail/prison authorizes might ignore such an order. A court might order DACA applications to be accepted, adn if they are not, might rule that deportations or other negative actions are unlawful. A court might hold persons who defy its orders in contempt, and send marshals to jail such persons. But if the executive branch in an organized way defies such orders, there is no judicial power to compel obedience to court orders.

This is why the judiciary has famously been called the "least dangerous branch" of the government: it cannot actually do anything without at elast the tacit cooperation of the executive.

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Does SCOTUS and the judicial branch have any way to actually enforce laws on the executive branch?

Yes.

The most common approach if an executive branch official defies a court order is to hold the official in contempt of court subject to incarceration and/or daily fines until the official complies or resigns. Typically, the lowest level official with the power to comply with the order is targeted for contempt of court charges.

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