As attorneys for former President Donald Trump work behind the scenes on an appeal following his conviction in the New York v. Trump trial, legal observers speculated to Fox News Digital about whether the presumptive Republican nominee is confident in his legal team ahead of his sentencing hearing – scheduled just four days before the Republican National Convention. 

While under normal circumstances, defense attorneys usually wait until after sentencing to file an appeal, legal analyst Phil Holloway questioned the lack of urgency from Trump’s lawyers in seeking federal intervention. 

“I’m curious to know why we have not seen any effort by Trump’s legal team to stay the looming sentencing,” Holloway told Fox News Digital. “I think there’s a reasonable argument to be made to a NY Appeals court, or even a federal court, that under the extraordinary circumstances present in this case, a stay of the NY proceedings is necessary to prevent a serious disruption of the federal electoral process.” 

“Every American citizen, at any rate, has an interest in being able to vote for the candidate of their choice in a presidential election. So we’re not talking about a normal and customary kind of an appeal,” Holloway said. “It’s unheard of in American jurisprudence. And so I think you can take the traditional rule book and throw it out. I think they need to pursue every conceivable avenue to get relief from another court.” 

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Holloway and David Gelman, another legal analyst who spoke with Fox News Digital, both separately referenced the Bush v. Gore case, when the U.S. Supreme Court ultimately ruled that Florida did not need to complete a recount in the 2000 presidential election, because it could not be accomplished in a constitutionally valid way within the time limit set by federal law. 

Gelman said that usually the Supreme Court or lower federal courts will not intervene in state decisions unless it’s a matter of “national importance,” as it was in 2000 and is again with the Trump case. 

“Look, it’s a Hail Mary. I’m not going to say it isn’t. However, you have nothing to lose. And, I think that this may, you know, get their attention a little more than a normal Hail Mary, if you will,” Gelman told Fox News Digital. “And also the Supreme Court is also hearing President Trump’s immunity claims right now. . . . So they’re very familiar with the arguments that are set forth with President Trump, even though this is not an immunity issue. So I think that it would be very prudent on the defense attorneys to throw that too, put up a motion before the Supreme Court to ask them to intervene and to file an emergency application to do so.” 

“We don’t know what they’re doing behind the scenes to prepare for the sentencing and obviously to prepare for the appeal. But I do wish we would see them acting with more of a sense of urgency regarding the appeal,” Holloway said. “If it were me, I might consider going to federal court now ahead of sentencing, seeking some kind of injunction to pause or to stop the sentencing from going forward, considering that you have the federal interest regarding the upcoming election at stake, and I think there’s enough federal issue involved to get a federal court involved in this.” 

The appeal must not go to the intermediate Appellate Division, which is Manhattan-based, and at a minimum go before the state Appellate Division of New York, if not the Supreme Court, Gelman said. 

Holloway said that if Trump’s legal team could “could somehow put a stop to the sentencing or pause it, they could perhaps begin the process of giving something up to the U.S. Supreme Court before the election.”

“If they have a client who gets sentenced to jail or even who is put on probation, that’s a significant restriction on the former president’s personal liberty,” Holloway said. “Either way, and it has an impact on the election. And I think there’s a significant federal issue there that would give the federal courts the jurisdiction they need to weigh in on, even before an appeal runs its traditional course.” 

Former President Donald Trump, sitting with attorneys Todd Blanche and Emil Bove, awaits the start of proceedings in his criminal trial at Manhattan Criminal Court in New York City, on May 29, 2024.  (JABIN BOTSFORD/POOL/AFP via Getty Images)

He also noted how the timing of the Republican convention could play into Trump’s attorneys’ strategy. “I think that it makes a big difference to a federal court potentially if you’re talking about someone who is the actual nominee of the party versus someone who is a presumptive nominee,” Holloway said. “I think that if you have the actual nominee facing the significant restrictions on his personal liberty, whether he’s in jail or whether he’s on probation or house arrest or some combination of all of that. I think that it’s a very real issue that the federal courts ought to get involved in, because there’s a strong argument to be made that they ought to sort of hit the pause button to stay any further proceedings until the election plays out.”

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Another case to consider is in Georgia, where the state’s court of appeals halted any proceedings in the 2020 election interference case until it hears Trump’s appeal to disqualify Fulton County District Attorney Fanis Willis. The hearing date is tentatively scheduled for Oct. 4. While Holloway and Gelman agreed that both Manhattan and Fulton County, Georgia, are heavily blue jurisdictions, Holloway noted that a small portion of northern Fulton County is traditionally more red, so because the jury pool comes from the county as a whole, Trump has a slightly better chance of getting a more friendly jury, compared to Manhattan.

“I think there’s a very good possibility that the DA, Fani Willis, will have to be recused and no longer be able to be on that case. And then once that happens, if another fresh set of eyes looks at it, meaning like the attorney general’s office or an independent authority of Georgia, I think that it’ll be thrown away,” Gelman said, comparing the cases. “I think they’re kind of apples and oranges.” 

As for Trump’s attorneys’ performance throughout the Manhattan trial, both Holloway and Gelman both said they were at a disadvantage from the start, due to the trial venue in New York City and Judge Juan Merchan, who refused to recuse himself from the case despite Trump’s team citing how the judge had donated to President Biden’s campaign.

Stormy Daniels is questioned by defense attorney Susan Necheles during former President Donald Trump’s criminal trial on charges that he falsified business records to conceal money paid to silence porn star Stormy Daniels in 2016, in Manhattan state court in New York City, May 9, 2024, in this courtroom sketch. (Reuters/Jane Rosenberg)

“If he wasn’t confident in his attorneys, you would probably hear by now that he has other attorneys on it,” Gelman told Fox News Digital. “We all know President Trump. He’s not really shy about letting his feelings known, and he’s not shy about firing people and hiring people. . . . He only wants the best people to work for him, and that includes attorneys. So by him not doing anything drastic, meaning by not firing Todd Blanche and the other people on the legal team and replacing them, you know, it shows me that he was happy with them. I know he’s not happy with the result and nobody is. But at the same time, you know, he’s a realist.” 

Gelman said that Trump’s attorneys in the Manhattan trial, Blanche, Emil Bove and Susan Necheles, “did an outstanding job with the facts that were given.” 

“I’ll be honest, I thought that there was no crime that was alleged, number one,” Gelman told Fox News Digital. 

“You cannot tell me with a straight face that there was not reasonable doubt,” Gelman said. I mean, you have two witnesses, specifically Michael Cohen and Stormy Daniels, who literally said on the stand they would like to see President Trump in jail. They had a bone to pick with him. They were out for blood. And then with Cohen, you had him, who pretty much is the walking, talking epitome of reasonable doubt.” 

Gelman said he thought Trump’s attorneys “kept their cool” while cross-examining Daniels and Cohen. 

“Trump’s legal team, they objected as much as they could. A lot of the objections that they put out were overruled,” Gelman told Fox News Digital. “Again, I think that the judge did a terrible job with that, because a lot of the objections should not have been overruled. And then you look on the other side where the prosecution, they objected to the same things – very, very similar – and their objections were sustained. So, the double standard was very noticeable.” 

While neither legal expert faulted Trump’s attorneys for calling former Michael Cohen legal adviser Robert Costello, Holloway admitted that the move “did backfire, because the judge handcuffed them.” 

“It’s very easy to Monday-morning-quarterback these things,” Holloway said. “They had a very tough jurisdiction. They had a very tough judge. They had a tough jury, and they were obviously in enemy territory. They did a very good job, considering where they were and what they had to work with.”