Trevor L.F. Headley Jr.
Businessman & Investor
United States Air Force — Aerospace Propulsion Specialist
Trevor Loxley Francis Headley Jr. is an American businessman, investor, and active duty member of the United States Air Force. Born on April 20, 2002, at Long Island College Hospital in Brooklyn, New York, he is the second child of Trevor Loxley Francis Headley Sr. and Rayer Anncaitis Headley. He has one sibling, Aliyah Headley, and three half-siblings — Jennifer, Chantelle, and Brigitte — from his father's prior marriage.
In 2007, Headley relocated with his family to Negril, Jamaica, where he attended Heinz Simonitsch School, a private institution in Montego Bay. In 2009, the family settled in Oviedo, Florida, where he subsequently graduated from Paul J. Hagerty High School in 2019. During his high school years, he developed a passion for music recording and production, and upon graduating established his own recording studio, Quintet Recording.
In 2022, Headley enlisted in the United States Air Force, where he became an aerospace propulsion system specialist. He was initially assigned to the 71st Rescue Generation Squadron isochronal inspection section at Moody Air Force Base in Valdosta, Georgia, responsible for the propulsion systems on HC-130J aircraft in support of combat search and rescue operations.
Concurrently with his active duty service, Headley enrolled at Western Governors University in 2024 and graduated in 2025 with a Bachelor of Science in Network Engineering and Security. Alongside his military career, he has pursued entrepreneurial ventures in business and real estate investment, reflecting the professional legacy established by his family.
Headley's trajectory reflects a deliberate convergence of military discipline, academic achievement, and entrepreneurial ambition — a lineage shaped by a family of attorneys, builders, and immigrants who each carved their own path in America.
A LEGACY FORGED ACROSS GENERATIONSTrevor Loxley Francis Headley Sr.
Trevor's father, Trevor Loxley Francis Headley Sr., was born on October 12, 1946, in Kingston, Jamaica, to Henry Headley and Ivy Wentt. He first visited the United States during the 1950s and became a naturalized U.S. citizen in 1972. Headley Sr. attended Long Island University in Brooklyn, New York, graduating in 1968 with a Bachelor of Arts. He subsequently enrolled at St. John's University School of Law in Queens, New York, where he earned his Juris Doctorate in 1972, graduating with distinction and earning placement on the Dean's List. He also served as Vice President of the St. John's University Alumni Association Brooklyn Chapter.
Following his graduation, Trevor Sr. began his legal career as a prosecutor and Assistant District Attorney in Queens County, serving from 1972 until 1974. In 1974, he founded his own firm, Trevor L.F. Headley & Associates, practicing as a trial attorney in negligence and criminal defense. Over the course of his career, he held several distinguished professional memberships, including service on the Federal Jury Task Force Committee, the Supreme Court State of New York Judicial Committee, and as a referee for the Committee on Judicial Conduct. In 1998, Headley Sr. expanded his legal credentials by graduating from Norman Manley Law School with a Certificate of Admission to the Jamaican Bar.
Trevor Headley Sr. was a Brooklyn-based defense attorney known for representing Lemrick Nelson Jr. in the 1990s federal civil rights trial concerning the 1991 Crown Heights riots. Working on high-profile cases, Headley often employed tough defense tactics, appearing in court alongside attorney Arthur T. Schmeiser in the 1997 federal case. Most notably, he served as primary counsel for Lemrick Nelson Jr. during his 1997 federal trial, which charged him with violating Yankel Rosenbaum's civil rights, following a 1992 state acquittal for murder. In court, Headley argued that the federal charges constituted a form of double jeopardy, distinguishing the proceedings from the Rodney King trial and focusing on the actions of police at the time. He was recognized for a direct, challenging approach to prosecution cases during this volatile legal period, and his work was covered extensively by The New York Times. Headley's involvement was deeply tied to the complex legal aftermath of the Crown Heights riots in Brooklyn — one of the most closely watched cases of that era.
As Covered By The Press
Crown Hts. Civil Rights Trial Is Set to Go to Jury Today
February 5, 1997Read Article →Youth Charged in Crown Heights Incident Is Arrested Again
June 24, 1995Read Article →In Twist, Defendant Admits to Stabbing in Crown Hts. in '91
April 29, 2003Read Article →Jury Clears Two Men in Attack on School Buses in Ozone Park
October 12, 1973Read Article →
In 2014, Trevor Sr. was diagnosed with Alzheimer's disease. He passed away in 2018 as a result of colorectal cancer. His legacy as a pioneering Jamaican-American attorney, civic professional, and family patriarch continues to inform the values and ambitions of his son, Trevor Loxley Francis Headley Jr.
A MATRIARCH OF RESILIENCE AND ENTERPRISERayer Anncaitis Headley
Trevor's mother, Rayer Anncaitis Headley, was born on July 20, 1970, in La Brea, Trinidad and Tobago. She was raised alongside seven siblings by her parents, Sheila Barban Davis and Gurrine John. In 1992, Rayer immigrated to the United States with her mother, settling in Brooklyn, New York, where she initially worked as a home health aide. She obtained U.S. citizenship in 1996.
By the year 2000, Rayer had established herself as an entrepreneur, founding RB's Realty and Construction. She further expanded her business portfolio by opening Simply Caribbean, a restaurant in Brooklyn, New York, which she later sold in 2004. Her entrepreneurial drive and resilience as an immigrant businesswoman have been a defining influence on her son's own approach to business and investment.