Strollen, I think there are different spectra along which we can look at the Supreme Court Judges. One is āpartisan hackeryā (and that IMO actually has two sub-spectra of āTrump-hackeryā and āGOP/wealthy donor-hackeryā) versus āconservative legal philosophyā (and there are sub-spectra of that as well).
Basically over the last couple of decades, despite an overall 5-4 GOP/Conservative majority, that majority has been often fragmented along these various sub-spectra lines and thus they donāt always get all 5 together to push the actual decision to the right. In a 5-4 court, a single dissent or a single sufficiently divergent concurrence, can prevent the Court from rendering a strongly GOP-oriented ruling. With a 6-3 majority, that calculus shifts and IMO that is going to cause substantially more reactionary opinions over the next few months/years.
As to why Trump has lost so much in court, there are 3 reasons. One is the lack of cohesion amongst the 5 conservatives on the Court as I have described. In addition, there has been a lot of incompetence by the Trump admin, especially in terms of the behavior of the administration setting up bad cases for their side. And also, the Trump admin has pushed some deeply one sided and extreme arguments that attempt to contradict or overturn decades (sometimes centuries) of precedent.
My big fears for the court going forward are not so much on the āTrump casesā b/c many of those cases are quite weak. And Iām not actually as worried about the ACA as some, b/c honestly the lower court opinions in that case are crap.
What Iām worried about with Barrett are the following:
Abortion. The Court may or may not rapidly and explicitly overrule Roe v. Wade but thatās irrelevant IMO. Thereās no question that with Barrett on the Court (and this is established by the precedent of Barrettās actual decisions such as the āfetal burialā case) the Court will allow restrictions on abortion such that states can, as a practical matter, take the right to choice away from their citizens.
Civil rights, minority rights, gay rights, trans rights, etc. There is fairly strong suggestive if not dispositive evidence in Barrettās record that she endorses a view of āreligious freedomā that includes at least some level of āfreedom to discriminateā and just as with abortion there are a LOT of ways that states can enable suppression/removal of rights while still overtly āallowingā the right to exist. An example of what I mean would be a decision that does not take away the right to gay marriage but does take away the ability of government to punish a county clerk who refuses to issue gay marriage licenses. Gay people would still have the ārightā to marry but would be unable to actually effectuate that right in many jurisdictions. Thatās just one example. I believe the Court with Barrett is going to do a LOT of harm in this area, more than most people expect or suspect. And, most of the harm will be subtle and indirect.
Also, in general Barrett is probably a vote for a more wealth/corporate focused economic jurisprudence although my sense of things is that her focus is more social than economic. You also get weird grey areas. For example one traditional conservative legal philosophy is to NOT extend too much deference to the government, but of course the GOP typically changes it tune when it is running the government. Trump in particular has exaggerated claims to deference to an absurd degree.
My biggest area of concern right now is voting rights / election law / throwing the election to Trump. And on that, Iāve been pretty bitterly disappointed, even in my cynicism, by the Roberts court. The Rucho gerrymandering case was just pure ass. I donāt really know for sure where Barrett is on these issues but it seems pretty likely sheās not in what I would consider a good place. The big question in my mind is will she be Roberts/Gorsuch level of bad on these issues (which is pretty bad IMO) or will she be Alito-bad on these issues (which is worse). And, thereās even worse out there IMO. If you want an example of a Judge I consider super dangerous on executive power/slavish obeisance to Trump type issues, look at Circuit Court Judge Neomi Rao. Iām hoping Barrett is not like Rao but I donāt know.