The CJ's foremost political role is to ensure the judicial branch of government is seen as a politically legitimate institution which wields its power against the other branches in a constitutionally and poltiically legitimate way. If that slips, congress can start hiring/firing; and the executive, in the end, controls the guns -- they can be arrested.
To avoid being arrested or fired, the court has to keep all sides believing the rules they set are fair.
They have no power, in the end, but the power they are allowed to have. They govern by consent of the other branches, and that's trivial to take away
The other aspect I think in play here is that the current executive branch pretty much just ignores every court order it doesn't like, and the Court can't enforce any ruling it makes, because that's the executive branch's job. I think Roberts knows if the Court pulls against Trump very hard, it could lead to a showdown where Trump just... does what he wants anyways, which would destroy the perceived power of the Court. I think Roberts has tried to dodge a lot of law and a lot of rulings to avoid clear positions on the President which he would, in turn, ignore.