"That does not constitute a conflict warranting recusal under New York law any more than any of the other attenuated and/or long-ago information Trump's team has already used it as the basis for not one or two, but three recusal motions, all of which have been denied," Rubin writes.
"But putting all of this aside, there's still a conundrum here."
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In his filing, Trump argued that vocal support for Vice President Kamala Harris expressed by Michael Nellis, founder of Authentic Campaigns, proves Merchan has a political stake that makes it impossible to issue a sentence as early voting in the upcoming election is underway.
Merchan has three times refused to recuse himself, most recently on Wednesday, arguing his daughter's work does not influence his legal judgment as a judicial ethics board affirmed earlier in proceedings.
Nellis, Authentic Campaign founder, denies the firm had a contract to work with Harris' presidential campaign or ever communicated with Harris' or Biden's campaign about the Trump trial.
"The accusations against us are absurd and completely false," Nellis wrote on X. "However, this has not stopped MAGA world conspiracy theorists from harassing our employees and sending death threats to some of our families."
But Trump also argues the Supreme Court ruling that bars prosecution on official presidential acts throws into question evidence presented at trial, namely public statements the then-president made on Twitter.
"[The District Attorney's office] should not be permitted to file a public sentencing submission that will include what the Supreme Court described as the 'threat of punishment,'" Trump's lawyers argue.
In Rubins' analysis, she points to two key points in the two criminal cases against Trump.
The first is that Trump was allowed to appeal on immunity in special Jack Smith's case before it ever came to trial in Washington D.C. federal Judge Tanya Chutkan's courtroom, Rubin writes.
The second is that Manhattan District Attorney Alvin Bragg, the hush money prosecutor, presented as evidence tweets Trump wrote as president and now argues were inadmissible as official acts.
"Does that mean the denial of a motion to set aside the verdict (predicated on the admission of official act evidence) must also be immediately appealable?" Rubin asks. "Trump says yes."
Rubin isn't so sure.
"The Court's holdings that immunity decisions must be made 'at the outset' of the case and are appealable before trial don't necessarily apply to evidence," Rubin writes. "But it's also not crystal clear that they don't."
Rubin dismisses Trump's claims of election interference but admits Trump's lawyers have raised an important point.
"Strip away the baseless accusations of judicial conflict & prosecutorial malice, and the letter raises a serious, unanswered procedural question," Rubin concludes. "I'll predict Merchan will forge ahead--but to me, even Team Trump's strategic delay notwithstanding, it's not an easy call."
Rubin's concerns were not reflected in analyses from other law experts who agreed Merchan would likely proceed as planned.
Andrew Weissmann, a former federal prosecutor from New York City, argued that there was no reason to delay the sentencing hearing as the sentence itself could be adapted to fit his schedule depending on the outcome of the election.
"If Trump loses the election, there is no reason he can’t go to jail then," Weissmann said. "If he wins, a state jail sentence will likely get put off until after he leaves office (good luck on whether that will ever happen especially if the alternative to not leaving is going to jail)."
National security expert Bradley Moss noted Trump has repeatedly worked to delay proceedings in the four criminal court cases he faced after his presidency ended, saying, "It's a pattern with this guy."
Former federal prosecutor Joyce Vance said simply, "Judge Merchan should give this one a hard pass."
