(WILMINGTON, Del.) -- With attorneys buzzing around him, Hunter Biden sat quietly at a desk Wednesday in the Wilmington, Delaware, federal courtroom -- hands folded, jaw locked -- where hours earlier he had entered in hope of putting his legal tribulations in the rearview mirror.
It was the most consequential moment in a day filled with them: both sides frantically seeking to resurrect a painstakingly negotiated plea agreement after a prosecutor declared "there is no deal" and Biden's lawyer could be heard saying to prosecutors, "Rip it up."
Under questioning from the judge, fissures had emerged as a result of the two sides' interpretation of a key passage in the agreement: Paragraph 15, which outlined in broad language the scope of Hunter Biden's immunity from additional criminal charges.
It states that the government would "agree not to criminally prosecute Biden outside of the terms of this agreement for any federal crimes encompassed by the attached statement of facts, Attachment A to the Diversion Agreement, and the statement of facts attached as Exhibit 1 to the Memorandum of Plea Agreement filed this same day," the judge read in court.
A copy of the memorandum obtained by Politico and authenticated by a source to ABC News included the same language. Details in that document and in paraphrased commentary from Wednesday's hearing shed fresh light on the deal brokered by the parties after the Justice Department's five-year probe of President Joe Biden's son -- an agreement that Judge Maryellen Noreika declined to approve at the end of Wednesday's hearing.
Attachments to the deal described how, in the period from 2017-2018, Hunter Biden "continued to earn handsomely and spend wildly" the large sums of money he made from business endeavors in Ukraine, China, and Romania -- some $2.6 million in 2018 alone.
"However ... in the throes of addiction, Biden essentially ignored his tax obligations," Leo Wise, the lead prosecutor, told the judge.
By 2019, Hunter Biden had "spent almost the entire sum" of his 2018 income "on personal expenses, including large cash withdrawals, payments to or on behalf of his children, credit card balances, and car payments for his Porsche," Wise said.
Those outstanding tax obligations -- ultimately totaling hundreds of thousands of dollars -- went unpaid until 2020, when a third party paid the IRS more than $2 million to relieve Biden of his tax burdens, interest and penalties. ABC News has reported that Kevin Morris, an attorney and confidant to Biden, made those payments.
In the courtroom, Judge Noreika repeatedly criticized the deal's "form over substance" and puzzled over whether the two documents -- the plea agreement on tax charges and the diversion agreement on the felony gun charge -- were linked or separate.
Noreika's line of questioning on that matter precipitated her decision to defer approval of the agreement and request additional briefing, giving the parties 30 days to resolve any outstanding issues.
"These agreements are not straightforward and they contain some atypical provisions," she said. "I am not criticizing you for coming up with those, I think that you have worked hard to come up with creative ways to deal with this. But I am not in a position where I can decide to accept or reject the Plea Agreement, so I need to defer it."
Experts said the deal does indeed bear some uncommon features, particularly in the way prosecutors structured Biden's immunity from future charges.
Prosecutors included details about Hunter Biden's foreign business endeavors into the plea deal on the misdemeanor tax charges, but wrote the immunity standards into the diversion agreement -- the much-cited Paragraph 15 -- which would include "any federal crimes encompassed" in the statement of facts for the plea agreement.
Lucian Dervan, a law professor at Belmont University, said the judge seemed concerned that the decision to handle immunity in the diversion program rather than in the plea agreement "might have removed that issue from her purview."
In most venues, judges don't typically weigh in on diversion agreements, Dervan explained -- those arrangements are typically treated as a private contract between prosecutors and defendants, depriving judges from scrutinizing them in detail.
"The judge didn't seem to like that," Dervan told ABC News.
Will Scharf, a former federal prosecutor, framed it as an attempt to "hide the ball" from the judge.
"[Prosecutors] put the facts in the plea agreement, but put their non-prosecution agreement in the pretrial diversion agreement, effectively hiding the full scope of what DOJ was offering and Hunter was obtaining through these proceedings," Scharf, currently a Republican candidate for attorney general in Missouri, tweeted late Wednesday.
Judge Noreika not only scuttled the structure of the deal, but her meticulous line of questioning also exposed gaps between the two parties' understanding of the nature and substance of Hunter Biden's future legal exposure.
Because the statement of facts included details about Biden's work in Ukraine and China, attorneys for Biden interpreted the immunity element to cover those overseas business endeavors. Prosecutors balked, framing the immunity deal in far narrower terms.
"So there are references to foreign companies, for example, in the facts section," Noreika said. "Could the government bring a charge under the Foreign Agents Registration Act?"
"Yes," Wise replied.
That exchange prompted Chris Clark, an attorney for Biden, to state: "As far as I'm concerned, the plea agreement is null and void."
The court went into recess and attorneys for both sides entered a frenzied cycle of negotiations -- huddling privately and then meeting in the middle of the courtroom to negotiate. Between private consultations with his attorneys, Hunter Biden sat stoically as others around him worked to hammer out his fate.
When Noreika gaveled court back into session, Clark said he was "prepared to agree with the government that the scope of paragraph 15 ... broadly relate to gun possession, tax issues, and drug use."
In the aftermath of the judge's decision to defer her approval, experts seem to agree that a pathway exists to an acceptable agreement.
"It seemed like everyone was on the same page at the end, and I assume when the document is re-created it will be modified to make that sentiment more clear," Dervan said. "I don't see that as a huge impediment to moving forward."
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