Prosecutors Seek To Bar Advice-Of-Counsel Defense In Bubba Bozo Trio Trial

Motion asks judge to require waiver of attorney-client privilege or block argument at trial.

Former City Attorney Ron Ramsingh, left along with his brother, former CBO Raj Ramsingh and longtime Code Enforcement Director Jim Young are facing 26 felony counts in what remains an ongoing City Hall corruption investigation. / MCSO

Prosecutors in Monroe County moved Tuesday afternoon to block three former Key West officials from arguing they relied on legal advice when responding to subpoenas in a criminal investigation unless they first waive attorney-client privilege and allow questioning of the attorneys involved.

The motion, filed Feb. 10 in Monroe County Circuit Court, asks a Judge Mark Jones to prevent defendants Ronald Ramsingh, Rajindhar Ramsingh and former Code Enforcement Director James Young from raising an “advice of counsel” defense unless they provide a written waiver allowing prosecutors to question outside lawyers who reviewed subpoena responses tied to the case. All three defendants are being tried together on criminal charges stemming from the same investigation with several other offshoot cases involving the CBO.

The filing was submitted by Assistant State Attorney Colleen Dunne on behalf of State Attorney Dennis Ward of the 16th Judicial Circuit.

The defendants are charged with tampering with physical evidence in connection with the alleged non-submission or incomplete submission of text messages requested by State Attorney’s Office investigative subpoenas. The cases are part of an ongoing investigation into the actions of the Ramsinghs and Young while they served in senior roles within Key West city government.

A Monroe County grand jury in 2025 returned a combined 26 felony indictments against the three men in what has become known locally as the “Bubba Bozo Trio” corruption probe, a long-running investigation into alleged misconduct at City Hall.

Court records show Rajindhar “Raj” Ramsingh faces 21 felony counts, including two first-degree felonies and one second-degree felony, while Ronald Ramsingh faces four third-degree felony counts and Young faces one third-degree felony count.

All three have pleaded not guilty and are presumed innocent unless and until proven guilty beyond a reasonable doubt.

The investigation’s roots trace back to subpoenas issued for text messages and email records from city officials. Authorities later alleged that not all requested communications were produced, a development that helped trigger a broader probe and a scathing grand jury report tied to the Corradino Report, which outlined concerns about potential criminal conduct and oversight failures inside City Hall. The fallout included the public ouster of former City Manager Al Childress after he pushed back internally on the possibility of criminal behavior described in the findings.

The cases remain pending while investigations are ongoing and more indictments could be coming. The case of the Bubba Bozo Trip is widely viewed as the most significant City Hall scandals in years — trailing back to the indictment and unsolved disappearance of former Fire Chief Bum Farto while facing sentencing on drug smuggling charges.

According to the motion, outside attorneys Benedict Kuehne and Victoria Méndez were retained in September 2024 under a legal services agreement with the City of Key West to represent officials in connection with the State Attorney’s subpoenas, though they are not the attorneys of record in the pending criminal cases.

Prosecutors argued that depositions conducted in recent months suggest the defense may attempt to argue that responses to subpoenas were reviewed by or prepared with guidance from outside counsel. If the defendants claim they relied on legal advice, the State argues, prosecutors must be allowed to question those attorneys about what advice was given.

“If the defendants’ positions are that they rely upon the discussions, review and/or advice of outside counsel, the State should be allowed to inquire into that subject matter,” the motion states.

Without a waiver of privilege, prosecutors are asking the court to bar the defendants from raising or implying that they relied on legal advice when responding to the subpoenas.

The filing also states that if any defendant claims reliance on advice from Ronald Ramsingh in his role as city attorney at the time, prosecutors would seek to question him on that subject as well.

The City of Key West attorney’s office indicated that under the legal services agreement, written waivers from the defendants would be required before the outside attorneys could be questioned about their communications with the officials, according to the motion.

The filing seeks a pretrial ruling preventing the defense from referencing advice of counsel unless those waivers are provided. A hearing on the motion had not yet been scheduled as of Tuesday evening.

The trial for the Bubba Bozo Trio is set to begin on April 13, 2026, although delays are expected as both sides hash through mounds of legal issues.