"We've given millions and millions of pages and he says give more, give more, always give more," Trump protested in May.
Trump ultimately relented and sat for a deposition, invoking his Fifth Amendment right nearly 450 times.
After James filed her lawsuit last month, Trump requested that the case be transferred from Engoron's court to the court's Commercial Division. An administrative judge on Wednesday denied his motion, meaning that the case will remain before Engoron, according to Bloomberg News.
The ruling leaves Engoron, "who is already VERY knowledgeable about the alleged years-long fraud, in place to hear the NYAG's motion to enjoin the Trump Org. from moving material assets," tweeted NBC News legal analyst Lisa Rubin.
James had asked the court to keep the case before Engoron as a "related matter" and last week filed a motion for a preliminary injunction to bar the Trump Organization from transferring assets.
James in the filing revealed that the Trump Organization registered a new company called "Trump Organization II LLC" in Delaware on the same day that she filed the lawsuit.
"Beyond just the continuation of its prior fraud, the Trump Organization now appears to be taking steps to restructure its business to avoid existing responsibilities under New York law," the filing said.
Trump attorney Alina Habba lashed out over the motion, calling it "nothing more than a thinly-veiled attempt to keep this case with Justice Engoron rather than have it transferred to the Commercial Division where it belongs."
Habba has repeatedly clashed with Engoron in court. Habba in February pushed Trump's claims that James was biased against him in court, interrupting the judge and drawing a rebuke from his clerk, Allison Greenfield.
"When the judge speaks, you need to stop speaking," Greenfield repeatedly told Habba, according to Insider.
Engoron ultimately ordered Trump and his adult children to comply with the subpoenas.
"The target of a hybrid civil/criminal investigation cannot use the Fifth Amendment as both sword and a shield; a shield against questions and a sword against the investigation itself," he wrote.
Trump refused to comply with the subpoena and James went back to court to hold Trump in contempt. Habba during a May hearing complained about the judge's rulings in the case.
"If you would like a bunch of more affidavits, you can order that," Habba snapped. "You can order anything you like."
Engoron held Trump in contempt and at one point fined him $10,000 per day for refusing to comply with the subpoena.
"I don't understand why we are still in contempt," Habba complained during a June hearing after Engoron refused to lift the order until Trump fully turned over documents in the case. "I think the opinion is based on who my client is," Habba claimed, "and that's concerning to me."
Trump and Habba have repeatedly claimed that he is the victim of political discrimination.
"There's no viewpoint discrimination," Engoron said during a hearing in February after Habba claimed James had "disdain" for Trump and argued that he was a member of a "protected class."
"What protected class is he a member of?" the judge pressed.
"His political speech," Habba replied. "If he was not sitting as a Republican and was not a former president who might run again, this would not be happening. So she is discriminating against him for that."
Engoron noted that protected classes include race, gender, and religion.
"Donald Trump doesn't fit that model. He's not being discriminated against based on race, is he? Or religion, is he? He's not a protected class," Engoron said. "If Ms. James has a thing against him, OK, that's not in my understanding [of] unlawful discrimination. He's just a bad guy she should go after as the chief law enforcement officer of the state."
Judge Arthur Engoron ruling / screengrab