Whoever did the filing had the internal memo in hand and didn’t bother to proofread what got filed. That’s the kind of sloppiness that gets lawyers fired.
About the only thing worse for a lawyer than going into court empty-handed is going into court having accidentally told the judge that you’re empty-handed. That’s exactly what appears to have happened to Justice Department lawyers representing the Transportation Department in Metropolitan Transportation Authority v. Duffy, a lawsuit in federal court in New York over DoT’s effort to revoke federal approval of New York Governor Kathy Hochul’s much-despised congestion pricing plan imposing tolls on drivers through Manhattan below 60th Street.
This is a federal case because Congress since 1916 has demanded that roads built with federal highway funds be free of tolls, but a 1991 statute exempted “congestion pricing pilot projects” approved by the Secretary of Transportation. The big-picture legal question is whether the term “pilot project” implies that approval is temporary and conditional, or whether it is permanent and irrevocable: Once the Secretary of Transportation approves an experiment, are all future Secretaries of Transportation barred from revoking that approval until the end of time? As part of the Biden administration’s last-minute push to entrench its policies (which also included Homeland Security Secretary Alejandro Mayorkas purporting to make Temporary Protected Status for Venezuelan immigrants irrevocable by his successor), Pete Buttigieg granted approval to congestion pricing. Sean Duffy revoked that approval, and the MTA sued, arguing that what Joe Biden could do, Donald Trump could not undo.
But, as often happens with these things, there are also a bunch of in-the-weeds legal arguments that could trip up one side’s position. What appears to have happened is that three assistant U.S. attorneys prepared an eleven-page, single-spaced memo dated April 11 for their client — the senior DoT trial attorney overseeing the defense of the case — assessing the MTA’s arguments, and they concluded:
There is considerable litigation risk in defending [Duffy’s] February 19, 2025 decision against plaintiffs’ claims under the Administrative Procedure Act, that the decision was contrary to law, pretextual, procedurally arbitrary and capricious, and violated due process. For the reasons outlined below, it is unlikely that Judge [Lewis] Liman [of the Southern District of New York] or further courts of review will accept the argument that the CBDTP [the congestion pricing plan] was not a statutorily authorized “value pricing” pilot under the Value Pricing Pilot Program (“VPPP”)…The Secretary provides two reasons why the CBDTP is not an eligible pilot project under the VPPP statutory language: (1) the program constitutes impermissible “cordon pricing,” which is not authorized because it does not offer a toll-free option, and (2) the level of CBDTP tolls has been set primarily by the need to raise revenues rather than prevent congestion. Neither of these reasons is likely to convince the Court. . . .
It is very unlikely that Judge Liman or further courts of review will uphold the Secretary’s decision on the legal grounds articulated in the letter. Defending the case on this basis, with the most likely outcome being vacatur of the Secretary’s decision or remand to the agency for further administrative process, will only serve to delay FHWA’s elimination of the CBDTP. The agency will have to answer the MTA’s and intervenors’ complaints, compile and produce the administrative record, and then the parties will engage in briefing, likely oral argument, and await a decision from Judge Liman—which is exceedingly likely to be averse to the agency….We welcome further dialogue as we continue to litigate this matter. Please let us know if you would like to schedule a call or meeting to discuss.
The memo went on to offer an alternative method of terminating the congestion pricing plan that might be on more solid legal ground. So far, so good: Lawyers defend things all the time when they think the other side has a stronger argument. Responsible lawyers, whether for the government or a private client, can and should warn their own client of weaknesses in the case while publicly making the best arguments they have.
Unfortunately for the AUSAs and DoT, somebody — presumably in the U.S. Attorney’s office — accidentally filed this memo yesterday evening as a letter to Judge Liman. Now, as a matter of ethical best practices, if you are opposing counsel or a judge and somebody accidentally sends you a privileged internal communication (it happens; I’ve never done it, but I’ve been on the receiving end), you’re supposed to give it back without reading it. As a legal matter, there are two privileges (the attorney-client privilege for advice to clients, and the attorney work product privilege for things written in anticipation of litigation), and while you can waive the work product privilege just by being careless about the confidentiality of your work product, it’s not so easy to waive the attorney-client privilege by accident, because the privilege belongs to the client, not the lawyers.
But in this case, they filed the letter on the public docket where everybody could see it, and once it’s noticed and published, you can’t unring that bell, no matter what the legal ethics are among the people involved in the case. Judge Liman may still do the right thing and disregard the memo, but this will be a giant egg on the faces of the people defending this lawsuit. And it really is inexcusable. The docket records that the letter was filed at 9:06 p.m., and it may well be that a proper letter to the judge was prepared and some paralegal was tasked with uploading into the electronic filing system and inserted the wrong document. (I’m assuming here a mistake, not deliberate sabotage, which is possible but seems less likely in this case). One way or another, however — maybe by means of a lawyer picking the wrong file to attach to an email — whoever did the filing had the internal memo in hand and didn’t bother to proofread what got filed. That’s the kind of sloppiness that gets lawyers fired.