Lawyers representing roughly 200 Democrats last month asked a federal judge to allow them to move forward on a lawsuit that would block President Donald Trump from accepting payments and other benefits from foreign governments doing business with his vast corporate empire while he serves out his remaining time in the presidency.

Nearly a year after it was initially filed, the lawsuits first hearing was held last month in a U.S. District Court in the District of Columbia where, for two hours, lawyers for both sides battled it out over whether or not individual lawmakers had the right to sue the president over alleged emoluments violations without Congresses approval first.

The case was overseen by Judge Emmet Sullivan who, although cautioning observers not to read to deeply into his questioning, though he seemed sympathetic to Democrats arguments.

Early on during the hearing, Sullivan said that the Constitution appears to suggest that those who hold federal office must first get the permission of Congress before accepting any kind of foreign gift or gratuity, that’s “crucial,” Sullivan said addressing lawyers on both sides.

Sullivan also referred to a statement by attorney Brianne Gorod, representing the lawmakers, as “troubling” when she told him that it is the president’s obligation to come to Congress first and request permission to receive any gifts or payments and, that without the president’s request Congress is essentially powerless in letting him accept any gifts or payments he may receive.

Brett Schumate representing the Trump Administration and an attorney for the Justice Department, however, refused to concede any ground over the matter arguing that lawmakers that wish to bypass Congress and press their claims in court need official authorization to do so, stating that “those institutional injuries can’t be asserted by individual members of Congress.”

50 Celebrities Who Have Died In 2018 – Tribute Slideshow

Sullivan acknowledged that arguments presented by the defense appeared to be an overreach.

Lawyers for the Trump Administration, however, appear to be caught between a rock and a hard place as two similar lawsuits are already being bitterly waged against them, and concession in any one of them could mean the loss of all three.

In December, a federal judge in New York threw out a similar suit on the grounds that it raised “a non-justifiable political question.” It is currently in the process of being appealed by the group Citizens for Responsibility and Ethics in Washington (CREW). Another lawsuit brought forward by the state of Maryland alleges businesses may suffer competitive harm from the president’s D.C. hotel.