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U.S. President Joe Biden’s son Hunter Biden arrives for a court appearance in Wilmington, Del., on July 26.Julio Cortez/The Associated Press

The plea deal in Hunter Biden’s criminal case unravelled during a court hearing Wednesday after a federal judge raised concerns about the terms of an agreement that has infuriated Republicans who believe the president’s son is getting preferential treatment.

Hunter Biden was charged last month with two misdemeanor crimes of failure to pay more than US$100,000 in taxes from over US$1.5-million in income in both 2017 and 2018 and had been expected to plead guilty Wednesday after he made an agreement with prosecutors, who were planning to recommend two years of probation.

But U.S. District Court Judge Maryellen Noreika, who was appointed by former U.S. president Donald Trump, raised multiple concerns about the specifics of the deal and her role in the proceedings. The plan also included an agreement on a separate gun charge – Mr. Biden has been accused of possessing a firearm in 2018 as a drug user. As long as he adhered to the terms of his agreement, the gun case was to be wiped from his record. Otherwise, the felony charges carries 10 years in prison.

The overlapping agreements created confusion for the judge, who said the lawyers needed to untangle technical issues – including over her role in enforcing the plea deal – before moving forward.

“It seems to me like you are saying ‘just rubber stamp the agreement, Your Honor.’ This seems to me to be form over substance,” she said. She gave defence lawyers and prosecutors 30 days to explain why she should accept the deal. In the meantime, Mr. Biden pleaded not guilty to the tax charges.

The collapsed proceedings were a surprising development in the yearslong investigation, and a resolution that had been carefully negotiated over several weeks and included a lengthy back-and-forth between Justice Department prosecutors and Mr. Biden’s attorneys.

The plea deal was meant to clear the air for Hunter Biden and avert a trial that would have generated weeks or months of distracting headlines. But the politics remain as messy as ever, with Republicans insisting he got a sweetheart deal and the Justice Department pressing ahead on investigations into Mr. Trump, the GOP’s 2024 presidential primary front-runner.

Mr. Trump is already facing a state criminal case in New York and a federal indictment in Florida. Last week, a target letter was sent to Mr. Trump from special counsel Jack Smith that suggests the former president may soon be indicted on new federal charges, this time involving his struggle to cling to power after his 2020 election loss to Joe Biden.

Republicans claim a double standard, in which the Democratic president’s son got off easy while the president’s rival has been unfairly castigated. Congressional Republicans are pursuing their own investigations into nearly every facet of Hunter Biden’s dealings, including foreign payments.

On Wednesday, the judge asked Hunter Biden to be more specific about his business relationships and to discuss his substance use issues as she combed through the plea agreement. She asked him to name the Ukrainian and Chinese entities referred to without name in the agreement.

She also asked him the last time he used alcohol or drugs and whether he was currently receiving treatment.

Hunter Biden answered June 1, 2019, and said he was not currently in treatment, though he did say he was in an anonymous support program for his substance issues.

President Joe Biden, meanwhile, has said very little publicly, except to note, “I’m very proud of my son.”

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