The federal judge overseeing Hunter Biden‘s tax evasion case ordered him to follow several measures after he pleaded not guilty following an unexpected delay to his plea deal, including an order to maintain a job.

Biden appeared in federal court Wednesday in Wilmington, Delaware, for what was expected to be a formality after he accepted a plea deal last month with U.S. Attorney David Weiss‘s office, settling tax and gun charges. Instead, the 53-year-old son of the president pleaded not guilty to the charges, as lawyers seek to work out a revised deal over his failure to pay taxes and lying about his drug addiction on a form when he purchased a gun.

As part of Hunter Biden’s release conditions, U.S. District Judge Maryellen Noreika ordered the first son to abstain from drugs and alcohol, submit to testing and substance abuse therapy, and “actively seek employment,” among other stipulations.

During the hearing, Hunter Biden told Noreika that he’d maintained sobriety since the summer of 2019. He was first treated for alcohol abuse in 2003 and was last in an in-patient facility in 2018.

It is not clear whether the younger Biden is currently employed by anyone other than himself, though it’s apparent that his most recent high-dollar sources of income stem from lucrative art sales, compiled with additional revenue from his April 2021 memoir Beautiful Things.

One legal expert told the Washington Examiner that the stipulation to “actively seek employment” might require the younger Biden to actually be employed by someone other than himself, expressing doubt that prosecutors would constitute self-employment as a viable option for the first son.

Kevin C. McMunigal, a law professor at Case Western Reserve University who specializes in criminal law, said, “I don’t think there’s a clear answer” to how employment is defined but cast doubt that prosecutors would be comfortable with self-employment, noting, “It’s so hard to verify.”

“What does the word ’employment’ mean in the contract? I don’t think there is an easy answer to that. Although I would think the prosecutors would want him to be employed by someone else so that they could verify,” McMunigal said.

“If he’s employed by somebody else there’s more likely to be a schedule, you know, someone else demanding him to do certain things which would make him get his act together and would be easier to confirm,” he added.

Conversely, another Case Western criminal law professor, Michael Benza, described some of the stipulations on pretrial diversion agreements as “boilerplate language.”

“You know, you’ll have people coming into diversion programs where that is a normal criteria, and they already have a job. And it’s like, well, you don’t have to quit that job and then either reapply for your job you just quit, or you know, go try to find someplace else,” Benza said, noting that some stipulations may already be satisfied ahead of the agreement.

The first public glimpse of the younger Biden’s foray into the art world came in a 2019 ABC News interview where he revealed his Los Angeles-based art studio and paintings, saying at the time that such work “literally keeps me sane.” In 2021, New York gallery Georges Bergès debuted Biden’s paintings, some of which are priced at as much as $500,000.

The prices are intended to be set by the gallery without any influence from the White House and with strict conditions in place for the younger Biden to remain in the dark about who is purchasing his work. But despite President Joe Biden‘s vows that his official duties would remain separate from his family matters, some of his son’s art patrons appear to be politically and personally linked.

Two buyers of his pieces were discovered and reported by Business Insider, which named the patrons as Democratic donor Elizabeth Hirsh Naftali and Kevin Morris, a financial backer and friend of the president’s son who has lent more than $2 million to him to help support his family and pay back taxes that are subject to the ongoing investigation. Naftali is a Los Angeles real estate investor and philanthropist who has donated $13,414 to the Biden campaign and $29,700 to the Democratic National Campaign Committee this year alone. Vice President Kamala Harris also headlined a fundraiser she hosted in 2022.

The president appointed Naftali to the Commission for the Preservation of America’s Heritage Abroad in July 2022, and it is unclear whether Naftali purchased Hunter Biden’s paintings prior to her appointment or whether the first son may have supported her appointment.

Meanwhile, the younger Biden has continued to make large gains from patrons who remain anonymous, as one buyer purchased 11 of his paintings for $875,000. That same buyer has purchased a majority of the first son’s inventory already, amounting to $1.38 million total in sales.

In late August, Hunter Biden settled his child support case with the mother of their 4-year-old, which resulted in a reduction of his monthly child support payments. As part of that settlement, Biden agreed to “assign to the child” some of his paintings, which have an estimated value between $75,000 and $500,000 apiece.

The younger Biden has had a varied employment history since he graduated from Yale Law School in 1996. After working for a bank holding company called MBNA from 1996 to 1998, he began a stint at the Department of Commerce in 1998 through 2001, according to Open Secrets.

He later went into business with his uncle, James Biden, purchasing an international hedge fund known as Paradigm Global Advisers in 2006. Two years later, just before his father became vice president, the younger Biden started the consulting company Seneca Global Advisors in 2008, advising companies looking to expand overseas.

The younger Biden has been subject to years of scrutiny by Republicans who accuse him of profiting off of his father’s position. By 2014, the president’s son had already spent a year on the board of a Chinese private equity fund, CEFC, and the board of the Ukrainian energy company Burisma. It was also during that time that he was struggling with substance abuse addictions on top of accumulating massive debts and unpaid taxes.

But on top of existing criticism over his foreign business dealings, a dispute arose among the younger Biden’s legal team on Wednesday after prosecutors indicated that the plea deal wouldn’t preclude them from investigating whether Biden engaged in illegal foreign lobbying under the Foreign Agents Registration Act.

Because of that dispute not resulting in a “meeting of the minds,” as Noreika put it, there could be no deal.

As for whether the first son’s current creative endeavors will satisfy prosecutors, other legal experts pointed out that his recent sales to known Democratic donors may not “pass the smell test.”

“In terms of his art sales, when you have major Democratic donors, buying his ‘art,’ it also raises some red flags, including one who was appointed by President Biden recently to a position who had bought some of Hunter Biden’s ‘art,'” said Roger Severino, a fellow at the Heritage Foundation who was the director of the Office of Civil Rights for the Department of Health and Human Services under former President Donald Trump.

Severino said if Hunter Biden had “legitimate self-employment as an entrepreneur or business owner” it could meet the stipulation for the plea agreement.

“However, he has a history of getting these rather suspicious paid positions, such as what he was getting from Burisma in Ukraine when he had no background in natural gas or drilling. Yet, he was being paid loads of money. So if he tries that stunt again, I would imagine the court would look very suspiciously at that sort of ‘work,'” Severino said.