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The argument you put forth is thorough and cogent. I am a huge fan of the disrespected and thoroughly emasculated 9th and 10th amendments.
But.

You assume that if Trump can place this argument before a Federal judge they will be reasonable and he will prevail. This is akin to Charlie Brown thinking that Lucy will hold the football when he tries to kick it.

That has historically been the case. But Roberts is no longer the swing justice.
We know that Thomas has explicitly stated that Sullivan must be revisited, Alito is nearly as originalist as Thomas, Kavanaugh had his reputation smeared as much as anyone in history - and Scalia praised Gorsuch and mentored ACB.
And it was from listening to a Scalia speech online that I learned that "thorough and cogent” argument. The following article was written less than a year before Scalia’s death:
Scalia argued his view on “textualism” was the ultimate defense of the First Amendment. In March 2012, an Associated Press report said he told an audience at Wesleyan University that the Court’s early justices would be “astonished that the notion of the Constitution changes to mean whatever each successive generation would like it to mean. … In fact, it would be not much use to have a First Amendment, for example, if the freedom of speech included only what some future generation wanted it to include. That would guarantee nothing at all.” That opinion didn’t prevent Scalia from harsh criticism of what is widely viewed as one of the essential court rulings protecting free speech and a free press — the 1964 decision in New York Times Co. v. Sullivan. At the Newseum in the Aspen Institute 2011 Washington Ideas Forum, Scalia said the landmark ruling meant “you can libel public figures without liability so long as you are relying on some statement from a reliable source, whether it’s true or not. “Now the old libel law used to be (that) you’re responsible, you say something false that harms somebody’s reputation, we don’t care if it was told to you by nine bishops, you are liable,” Scalia said. “New York Times v. Sullivan just cast that aside because the Court thought in modern society, it’d be a good idea if the press could say a lot of stuff about public figures without having to worry. And that may be correct, that may be right, but if it was right it should have been adopted by the people. It should have been debated in the New York Legislature and the New York Legislature could have said, ‘Yes, we’re going to change our libel law.’” But in Times v. Sullivan, Scalia said the Supreme Court, under Justice Earl Warren, “… simply decided, ‘Yes, it used to be that … George Washington could sue somebody that libeled him, but we don’t think that’s a good idea anymore.’”
JUSTICE SCALIA: THE 45 WORDS — AND ORIGINAL MEANING — OF THE FIRST AMENDMENT
Having voted in 1960, I am old enough to remember when SCOTUS promulgated Sullivan (tho I don’t remember being wise enough to have been outraged by Sullivan). So I know that the prospects for overturning evil Warren Court precedents has never been as good as it appears now. Since Roberts would not lead such a movement, it is pretty much down to both Gorsuch and ACB, tho Roberts would have to go along with those two if he is, as claimed, mostly concerned about the reputation of the court and motivated to not let the choice of the author of the decision go to SCOTUS’ most conservative member, Thomas.
Apart from the sheer merits of the originalist case and the insults which have been felt personally by Thomas and Kavanaugh in particular (but have been seen and heard by all the rest), there is the issue of the Hunter Biden laptop, and the treatment of its revelations by the monopoly press. The national public didn’t know what the writers of the New York Post assayed to tell them; it’s hard to believe that Democrat vote fraud could have been sufficient to put him over the top in the swing states if their voters had known that, and its implications for a Biden presidency. SCOTUS will IMHO get the picture, and will want to protect the Republic by throwing out the Biden “victories” in the swing states and putting the choice of Electors back in the hands of those (Republican) state legislatures.
But that’s an exceedingly hot potato, and SCOTUS is likely to emphasize that those legislature can select Electors who will be pledged to any adults for POTUS and VP (tho not both from the Electors’ home states). Indeed, they don’t have to be pledged to anyone at all. And even with that fig leaf, SCOTUS needs to overturn Sullivan in order to protect itself from "education, media and government.” The wire services, their members/subscribers, and the FCC need to be on notice that their very existence depends on their good behavior - keep it up, and you’ll be sued into oblivion.
It is the function of free presses to express opinion as opinion and facts subject to libel damages if systematically false but systematically purported to be true. Facts are what courts determine, not what reporters claim.
Talk radio is known to be opinion, but in reality it is reaction to the sophistry of “the media.” And as the ancient Greeks learned, sophistry is opposed effectively only by “philosophy.” It is opposed, that is, not by engaging in a fruitless argument over who is more wise than who but by limiting one’s claims only to loving truth and being open to logic and facts.