‘Fundamentally Flawed’ New York Judge Blocks ICE Access To Rikers Island Over Alleged Adams Conflict

Authored by Jonathan Turley,

This week, New York Judge Mary Rosado issued an opinion in Council of City of N.Y. v. Adams. The court is blocking the city from allowing the federal government to maintain office space at Rikers Island. The reason is that Rosado agreed that Mayor Eric Adams had a conflict of interest and likely bargained away the access as part of a quid pro quo arrangement to get the Justice Department to drop criminal charges against him. 

The opinion is quite extraordinary and, in my view, fundamentally flawed. The opinion generated more heat than light on the proper handling of a conflict of interest.

The court recounts the testimony of Danielle R. Sassoon, Esq., Acting United States Attorney for the Southern District of New York, regarding a January 31, 2025, meeting with President Donald J. Trump’s Deputy Attorney General, Emil Bove, and the Mayor’s criminal defense counsel. She claimed that “Adams'[] attorneys repeatedly urged what amounted to a quid pro quo, indicating that Adams would be in a position to assist with [immigration] enforcement priorities only if the indictment were dismissed.”

After that meeting, on February 3, 2025, Mayor Adams’ criminal defense attorney, Alex Spiro, wrote to Bove that the prosecution of the Mayor will “become increasingly problematic as the Trump administration seeks to aggressively enforce immigration laws and remove undocumented immigrants …. [T]he federal government cannot possibly rely on Mayor Adams to be a fully effective partner in all situations in ongoing public-safety missions while he is under federal indictment ….”

Spiro further stressed that Mayor Adams’ “abilities to exercise his powers have also been complicated by his indictment” including his powers to “prevent[] the Office of the Corporation Counsel from litigating challenges to immigration enforcement, prevent[] appointed city employees from taking public stances against enforcement efforts, [and to] re-open[] the ICE office on Rikers Island ….”

One week later, on February 10, 2025, Bove directed federal prosecutors to dismiss with prejudice the pending criminal charges against Mayor Adams.

The plaintiffs allege that these negotiations traded away city policies or privileges in exchange for the dropping of the charges, a charge that Adams vehemently denies.

On February 13, 2025, after meeting with the Administration’s “Border Czar,” Thomas Homan, Mayor Adams announced that he would issue an executive order allowing federal immigration authorities to be present on Rikers Island. The next day, the Department of Justice filed a motion to dismiss all pending criminal charges against Mayor Adams.

After the announcement, a number of deputy mayors resigned in protest. Adams then appointed Randy Mastro as First Deputy and delegated to him the authority to “[p]erform any function, power or duty of the Mayor in negotiating, executing and delivering any and all agreements, instruments and any other documents necessary or desirable to effectuate any of the matters” related to public safety.

On April 8, 2025, Mastro issued Executive Order No. 50, authorizing the Department of Corrections to enter a Memorandum of Understanding with federal law enforcement agencies allowing them to maintain office space on Department of Corrections property, specifically Rikers Island.

The timing of these actions raised objections from many, both inside and outside City Hall. That included United States District Judge Dale Ho, who agreed to dismiss the criminal charges with prejudice, but not after lashing out at the administration. Ho wrote that “[e]verything here smacks of a bargain: dismissal of the [i]ndictment in exchange for immigration policy concessions.” He further warned that the suggestion “that public officials may receive special dispensation if they are compliant with the incumbent administration’s policy priorities … is fundamentally incompatible with the basic promise of equal justice under law.”

I disagreed with Judge Ho’s use of the order to opine on an alleged quid pro quo that was not established in the record or even material to his decision. Ho agreed that he could not “force the Department of Justice to prosecute a defendant” and agreed to dismiss the matter with prejudice. That was the correct and only decision that he could make. However, he further strongly suggested the need for an investigation but lamented that he “did not have the authority to appoint an independent prosecutor.”

I do not question Judge Ho’s sincere objections or the good-faith basis of many in raising this allegation. However, I do not believe that judges or justices should use their positions to opine on political or ethical issues that are not clearly before them. The issue before Judge Ho was solely the dismissal of a criminal case and he had no record, or in my view license, to hold forth on his unsupported suspicions in the case.

The matter, however, was raised and litigated directly before Judge Rosado by the city council, which sought to nullify the Executive Order as being violative of city ethical rules. Specifically, the city council cited New York City Charter § 2604(b)(3), which provides in pertinent part that “[n]o public servant shall use or attempt to use his or her position as a public servant to obtain any … privilege or other private or personal advantage, direct or indirect, for the public servant or any person or firm associated with the public servant.”

Judge Rosado found a likelihood of prevailing on the merits, citing Baker v. Marley, 8 NY2d 365, 367 (1960), that an action must be declared null and void when the action “directly or immediately affects him individually.” She specifically found:

Plaintiff-Petitioner has shown a likelihood of success in demonstrating, at a minimum, the appearance of a quid pro quo whereby Mayor Adams publicly agreed to bring Immigration and Customs Enforcement (“ICE”) back to Rikers Island in exchange for dismissal of his criminal charges. This showing is grounded in (1) Mayor Adams’ public statements; (2) Mayor Adams’ criminal defense attorney’s written overtures to the Department of Justice; (3) the temporal proximity between these overtures and Mr. Bove’s directive to dismiss the criminal charges against Mayor Adams; (4) statements from former Acting United States Attorney Danielle R. Sassoon and Assistant United States Attorney Hagan Scotten; (5) Mr. Homan’s statement that he will “be in [Mayor Adams’] office, up his b ___, saying, ‘Where the hell is the agreement we came to?’” and (6) the written findings by United States District Judge Dale Ho.

Although Defendants-Respondents deny any quid pro quo in conclusory fashion, this is insufficient, and almost expected. As wisely stated by Justice Anthony Kennedy, the quid pro quo need not be stated in express terms “for otherwise the law’s effect could be frustrated by knowing winks and nods. The inducement from the official is [violative] if it is express or if it is implied from his words and actions ….” Based on the record, Plaintiff-Petitioner has made a sufficient showing of an implied, if not an express quid pro quo based on Mayor Adams, Mr. Spiro, Mr. Bove, and Mr. Homan’s words and actions.

In my view, the decision is wrong on a number of key elements.

Who decides?

First, Judge Rosado heard this case despite the fact that there is a process for such allegations to be raised and adjudicated before the Conflict of Interest Board. Rosado recognizes the obvious problem and admits that

“[t]o be clear, the Conflicts of Interest Board is the preferred and proper forum for many garden variety conflict of interest disputes, such as those involving improper gifts, failures to disclose financial interests, and other financial conflicts.

However, the Conflicts of Interest Board is not equipped with the powers and tools to grapple with the case, which involves the promulgation of an Executive Order at lightning speed, upending a decree of New York policy barring federal law enforcement authorities from maintaining a presence on Department of Corrections property.”

I found the court’s logic on this portion of the opinion to be conclusory and counterintuitive. There is nothing in the law or regulations that defines the Board as focused on “garden-variety” conflicts. It is the system created by the city council to address conflict allegations and, while Judge Rosado believes that she can do better than the board, that is hardly a convincing basis to circumvent the process for the adjudication of such claims. Rosado ignores that this is a specialized body expressly tasked with such conflicts. It is unclear how the court is “better equipped” with its own limited staff to address such matters, other than having the ability to issue judicial injunctions.

Deception or Delegation?

Putting aside this act of judicial overreach, there is also the problem that the order was ultimately issued not by Adams but by Mastro. There are very compelling public policy reasons for taking this action. The city is struggling with the massive demands of its undocumented immigrant population. Before he was ever charged, Adams was viewed as a moderate on such questions who was open to greater federal enforcement. Many states and cities cooperate with federal authorities in this way as a matter of public policy.

Judge Rosado admits that there is a valid question of whether the delegation constituted a type of recusal or cleansing of the decision. However, she maintained that Mastro is not independent because he was appointed by Adams and reports to him. Moreover, she cited New York City Charter § 2604(b)(3), which states that delegating oversight or management does not necessarily erase a conflict of interest. She notes that Adams said publicly that he did not recuse himself and found:

“The Defendants-Respondents’ hyperbolic argument that if Mayor Adams cannot delegate to First Deputy Mayor Mastro, then there is nobody he can delegate to, is without merit. First Deputy Mayor Mastro, although an accomplished and highly educated attorney, is not independent of Mayor Adams and therefore cannot be considered impartial and free from Mayor Adams’ conflicts. First Deputy Mayor Mastro reports directly to Mayor Adams, is appointed by Mayor Adams, and can be fired by Mayor Adams. He is Mayor Adams’ agent.”

It is not clear, however, who would be sufficiently free of Adams’ authority to allow for them to make the myriad of decisions vis-a-vis federal authority. In this matter, Mastro and the Mayor’s office are arguing that he made an independent judgment on the merits of the policy. More importantly, Judge Rosado ignores the implications of her order. She never explains how the city is to function if any order dealing with the federal government could be viewed as part of a quid pro quo. There are a host of joint operations and programs with the federal government. Where does one draw the line and who then makes these decisions ranging from housing to prisons to voting? Rosado seems to shrug and say that anyone reporting to the Mayor or subject to his authority is not sufficiently independent.

The Order

Judge Rosado ultimately finds against Adams, but includes rhetoric exulting the prior pro-immigration policies that further undermines the opinion:

The Court finds that Plaintiff-Petitioner has demonstrated imminent and irreparable harm for purposes of obtaining a preliminary injunction. The harm to intangible assets such as damage to reputation, loss of goodwill, and brand tarnishment are routinely found sufficient to grant injunctive relief. New York City, which thrives as a global hub due in large part to its reputation as being a welcoming home for immigrant communities from around the world, risks having this goodwill and invaluable reputation irreparably damaged as a result of an Executive Order borne out of Mayor Adams’ alleged conflict of interest. New York City, through legislation and decades of policy, has established a reputation as a “Sanctuary City.” This reputation, and the goodwill built from decades of policy decisions, and which have provided New Yorkers with numerous intangible cultural and economic benefits, risks being irrevocably tarnished. The harm to New York City’s reputation as a Sanctuary City, and the goodwill with numerous communities that flows from that reputation, is best preserved through a preliminary injunction prohibiting Defendants-Respondents from acting on Executive Order No. 50.

…

The Court is also cognizant of threat of irreparable harm in a more concrete sense—that is the threat to detained New York State and City residents and their dignity. There is ample evidence that there is already a serious, imminent and ongoing risk that immigrant New Yorkers, and even foreign tourists to New York City, are being wrongfully detained. There are documented reports of individuals being deported to stranger third-countries, and New York City residents are taken into custody for expressing political views contrary to the federal government’s agenda. Residents who are here seeking asylum are being deported to countries they claim to have previously faced persecution for their sexuality, politics, or religion. And this concrete harm flows to the Plaintiff-Petitioner…

I was frankly astonished by the direct discussion of the Mayor’s criminal charges in the conjunction with negotiations over enhanced federal enforcement. While I understand the defense counsel’s job to seek any lawful avenue for relief, I would have immediately cut off such discussions as inappropriate from the perspective of the Justice Department. If such discussions occurred, there is a legitimate concern over a quid pro quo. However, this is not how courts should address such allegations. I believe both Judge Ho (who ruled correctly) and Judge Rosado (who did not) exceeded the parameters for their opinions with extraneous commentary. That is particularly the case with Judge Rosado. More importantly, I believe that Judge Rosado is simply wrong in circumventing the designated board for addressing conflicts of interest and issuing this sweeping opinion.

This is not an easy matter for any board or court. These meetings and the timing of these decisions raise obvious concerns. However, courts are not allowed to engage in conjecture. It is not just plausible but likely that Adams would have extended the access to Rikers Island even without any change in his criminal case.

I do not see the limiting principle in this decision. Adams is still the mayor and may have independent and good-faith reasons for orders that are favorable for the federal government. Indeed, his order was the correct one on the merits. While Judge Rosado never explores the countervailing benefits while writing at length on the costs to a city of immigrants, they are obvious and cannot be ignored. In other words, Adams had every reason to support federal enforcement as a Mayor who ran on making New York a safer city.

This matter should have been left to the Conflicts of Interest Board, and the decision itself is ill-considered and incomplete.