About US

Decades of Professional Experience

About Us – Cloak & Dagger Investigations

Cloak & Dagger Investigations and Consulting, LLC is a Florida Private Investigative Agency, License #A3100158.

In addition to licensing as a private investigative agency, we are also a State of Florida Notary Public and a Certified Civil Process Server (18th Judicial Circuit).

Managing Partner – James “JJ” Woolsey

Cloak & Dagger is led by Managing Partner James “JJ” Woolsey. Mr. Woolsey previously served with the Brevard County (Fla.) Sheriff’s Office, retiring at the rank of Commander.

He served on the command staffs of former Brevard County Sheriff Jack Parker, and current Sheriff Wayne Ivey.

Mr. Woolsey has over thirty years of professional law enforcement experience in management, investigations, intelligence, documentation, and special operations. He has worked, managed, supervised, or commanded in all areas of law enforcement including assignments in narcotics/vice, general crimes, surveillance, high-profile (major) crimes, organized crime, auto-theft, fraud, crimes against persons, and property crimes.

Mr. Woolsey served on the BCSO SWAT team during the duration of his career and served as the SWAT Team Commander for over ten years. He was instrumental in the creation of the Brevard County G.A.M.E.O.V.E.R. Task Force, a unit specializing in locating and arresting high-profile and dangerous fugitives wanted by any of Brevard County’s police agencies or the State Attorney.

In his capacity as Brevard County’s SWAT Commander, Mr. Woolsey provided oversight and management of all SWAT personnel, assets, and budgets. He planned, managed, or supervised over 500 high-risk operations, including search and arrest warrants, and barricaded subjects. He has personally worked and/or coordinated with the United States Secret Service on dignitary protection details for both the President and Vice-President of the United States, members of the United States Congress and foreign dignitaries.

Mr. Woolsey is recognized as a subject matter expert in Threat and Vulnerability Assessments as well as Risk Analysis for community businesses and government stakeholders. He has conducted numerous trainings in the areas of tactics, response to active-shooters, critical incident management, TCCC, vehicle assaults, room clearing and other trainings related to tactical operations.

Call us Today for a Consultation

(321) 403-2199

JJ Woolsey, Owner of Clok & Dagger Investigations
Brevard County Sheriff’s Office
Commander (Ret.) James “JJ” Woolsey

Managing Partner

Contact Us In Confidence

Explore Our Services