BREAKING: Key West Police Sergeant Indicted by Grand Jury After Alleged On-Duty Drug Solicitation via Text from Patrol Vehicle
Filing stands in stark contrast to internal probe that found no unlawful conduct; not taken into custody but given a Notice to Appear before Judge Mark Wilson.
KEY WEST, Fla. — A Monroe County grand jury has indicted Key West Police Sgt. David Kouri on a misdemeanor charge stemming from an alleged on-duty text message exchange, a move that sharply contrasts with a prior internal investigation that concluded his actions did not rise to the level of a criminal offense.
The April 8 indictment charges Kouri with one count of solicitation to deliver or sell marijuana under Florida law. In Florida, the charge is a first-degree misdemeanor punishable by up to one year in jail.
According to records obtained via FOIA requests and reviewed by Above the Fold, the allegation centers on a text message exchange obtained by the Monroe County State Attorney’s Office from Kouri’s phone. In the messages, Kouri allegedly asked a witness identified as Hailey Freeman for “pre rolls” and inquired about obtaining marijuana or a vape pen while on duty in his patrol car.
The exchange also includes messages in which Kouri appears to offer the recipient a ride, stating he was working until 5 p.m. “if u need a ride,” while indicating he was driving in the downtown area. The conversation suggests the other individual may have been intoxicated at the time.
Prosecutors allege the messages were sent during Kouri’s shift, raising questions about conduct and use of a patrol vehicle.
A charge of solicitation does not require a completed transaction. Instead, it alleges that a person requested or attempted to induce another individual to commit a drug offense — which the text exhancge appears to clearl show..
But internal Key West Police Department records obtained through public records requests show the same incident — which occurred on Sept. 9, 2025 — was previously investigated and resolved administratively, with findings that did not support criminal wrongdoing .
The case, logged as Professional Standards investigation PS 25-04, was initiated by Police Chief Sean T. Brandenburg and investigated by Lt. Jeffrey Dean. A personnel action form dated Oct. 29, 2025, identified Kouri, a patrol sergeant, as the subject of the inquiry .
The internal investigation examined potential violations of departmental policy, including unlawful conduct and conduct unbecoming an officer. Despite evidence that Kouri attempted to facilitate a marijuana exchange between civilians, the department did not sustain the allegation of unlawful conduct.
Instead, KWPD investigators concluded Kouri’s actions constituted “conduct unbecoming” and issued a written reprimand, with no suspension imposed — which broaches the question would a civilian that committed the same act not be pursued by KWPD and treated the same?
In a Jan. 26, 2026 disciplinary letter, Dean wrote that Kouri “attempted to facilitate the exchange of marijuana through two civilians,” noting that one individual had a medical marijuana card while the other was unconfirmed. The letter emphasized that marijuana remains a regulated substance under state law and that Kouri’s actions reflected poor judgment inconsistent with department standards. Under Florida Law, it is illegal to facilitate the transfer of marijuana products from one person to the other — regardless of whether either person has a medical card or not.
The final outcome of the Internal Affairs investigation and disciplanary action appears to rest squarely on the shoulders of a fact-finding memo submitted Jan. 21, 2026, by KWPD Capt. Jason Castillo, who relying on the investigation conducted by IA’s Lt. Dean, concluded there was no basis for unlawful conduct and recommended a written reprimand with no mention of suspension.
Supervisory records further show that Brandenburg, who initiated the complaint, indicated the matter was not resolved to his satisfaction, although his response was not fully completed with several boxes not checked.
The grand jury indictment — filed months after the internal investigation was completed — represents a stark departure from those findings.
Additional records show prosecutors subpoenaed a witness, Hailey Freeman, to testify before the State Attorney’s Office on April 2, 2026, as part of the investigation. According to information reviewed by Above the Fold, Freeman told investigators the suspected marijuana transaction was never completed.
Kouri was also given the voluntary opportunity to appear before the grand jury and answer questions, including who the narcotics were intended for. It remains unclear whether he appeared or responded.
The indictment comes amid a broader backdrop of legal challenges at Key West City Hall, including the 27 felony indictment counts filed against the so-called “Bubba Bozo Trio” — former City Attorney Ron Ramsingh, his brother and former Chief Building Official Raj Ramsingh, and former Code Enforcement Director Jim Young.
Despite the criminal charge, Kouri remains on active duty as of publication.
In response to questions, spokesperson Alyson Crean said, “The KWPD does not comment on ongoing investigations or litigation,” despite the fact that the internal investigation, findings and discipline were completed in 2025.
Emails to City Manager Brian Barroso, City Attorney Mayanne Downs and Assistant City Attorney Kendal Harden also went unanswered by deadline.
Kouri was not taken into custody following the indictment but was issued a notice to appear instead. His attorney , Joshua Bickman has filed a plea of not guilty, and his arraignment is scheduled for Friday, April 24, before Monroe County Judge Mark Wilson.
Kouri’s case was presented in open court before the 16th Judicial Circuit in Monroe County. Grand jury foreperson Jill Miranda-Baker signed the indictment, and Assistant State Attorney Colleen Dunne certified the proceedings.
Above the Fold has requested additional records from the State Attorney’s Office and KWPD and will update this story as more information becomes available.
All defendents are considered innocent until proven guilty in a court of law by a jry of their peers.
This is an evolving story. Watch this space.