Taking Down Trump 2.0 - Rule 6
Fighting Trump requires playing the long game. Don't shy away from lengthy court battles, even ones you may lose. And how will the new court challenges work? Here's the roadmap for those cases.
In the original rules of Taking Down Trump, Rule 6 was focused on “playing the long game” in the context of fights over statutes of limitation — but the principle underlying that Rule applies in a much broader set of situations when it comes to fighting Donald Trump, especially now.
The principle is simple to state but onerous to follow — unswerving relentless persistence, no matter how long it takes, no matter how many court proceedings, how many briefs, how many arguments, how many years. Run through the tape. Play all the way through the whistle.
That’s what “playing the long game” requires.
This was true in the Trump University case — where we endured a two-year detour on the case to win a massive victory on appeal of a statute of limitation question that drastically increased the amount of money we could win back for victims (probably from around $1-2 million to around $41-42 million). Playing the long game paid off: the appellate win paved the way for our landmark settlement win.
And it is equally and even more critically true in the new court challenges that have been or are about to be filed against the new Trump administration.
Let’s examine the roadmap for how these cases are going to proceed — indeed, what’s already happening to the ones that have just been filed (and there’s more on those court challenges over on the latest episode of the podcast).

1 - Filing the complaint and moving for a stay or TRO
The case begins with the plaintiffs and their counsel filing a complaint, in a federal district court (the lower-level trial courts in the federal system), laying out the alleged legal violations committed by the administration and requesting relief. Most of the time, they will go one step further — in addition to the complaint, they will file for a temporary restraining order (TRO), which aims to stop the alleged wrong from occurring or continuing until further court proceedings can take place.
Typically, a court will leap into action and decide a TRO within a few days. But because a lot of damage can occur even in a few days, courts will often issue an administrative stay even before the TRO is decided, to freeze the original status quo before any harm can be done.
In other words, there are a series of escalating pauses that a court can order, and they usually proceed as follows (with some over-simplification):
Administrative stay — a few days
Temporary restraining order — a few months
Preliminary injunction — a few years
For a TRO or a preliminary injunction (which we’ll discuss below), the court may only issue the order if the plaintiff demonstrates, among other things: (a) immediate and irreparable harm that is already occurring or is imminent, (b) likelihood of success on the merits when the case is completely decided.
As for the former, if a wrong can be righted just by paying someone money, then that is, by definition, a reparable harm — a harm that can be repaired. To issue a TRO or injunction, a court is looking for harms that cannot be undone so easily, where some or all of the damage may be permanent.
Like, say, tearing a family apart and sending some or all of the family members back to a country where they’ll be killed or imprisoned. Or halting cancer research and clinical trials, dooming late-stage cancer patients who could have been saved. Or firing an entire federal workforce or dismantling an office or agency, causing permanent damage to employees’ job records, reputations, and health, not to mention the difficulty or impossibility of re-creating the office or workforce.
And on the latter, “likelihood of success on the merits” (LOS) effectively means a sneak peek at whether the plaintiffs’ case is a winner or not — an early quick take from the court. These are not binding: there are plenty of cases where a judge initially ruled for the plaintiffs on LOS but ultimately ruled for the defendants once all the evidence and arguments were presented. But it often provides a spoiler as to which way the court is leaning, and the point of this legal procedure is to say: Ok, plaintiff, you have a solid chance of winning this case, so we will issue this order to freeze everything until you can have your full day in court.
In a number of the court challenges to the administration that have already been filed, TROs and administrative stays have already been granted — and we will see many, many more of these in the weeks and months ahead.
2 - Moving for a preliminary injunction
Consider the preliminary injunction to be a more durable version of the TRO. Courts will decide a TRO in a matter of days. Then they will turn to the lawyers and give them a much longer briefing schedule, followed by an oral argument in court, to determine whether the court’s freeze should be extended for the entire duration of the case — which will often take years to decide.
Preliminary injunction proceedings normally take a few months, sometimes longer in more complex cases with a lot of complicated issues or a lot of different parties. A court will allow the parties to submit evidence and arguments for why or why not the injunctive relief should be ordered, followed by a longer decision. When a judge does order a preliminary injunction, it is often a much stronger tell that the court is leaning toward the plaintiffs, given the additional evidence and arguments considered. It carries a lot more heft.
Next we’ll continue the rest of this look at playing the long game and the roadmap for the court challenges ahead, in the next few days.
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Great roadmap.