

The Trump administration is operating on a “it’s not legal/constitutionally protected until a judge says it is” and if they punish you before the judge says you don’t deserve punishment, oh well!
So in this case, because we don’t have any case law saying that deportation is an infringement of the 1st amendment, Trump gets to say it isn’t until a judge says otherwise. At which point maybe Trump will obey the court, or (probably) not.
It’s bullshit and backwards, but that’s what we’re up against.
Afaik they’d have to go through customs for the country they’re trying to enter. I can’t recall ever having to deal with US customs when leaving the US, it’s always been the country I’m traveling to.