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May 20, 2024

Music industry mourns loss of Hayward J. Gregory Jr., founder of Gregota Music LLC, at 74

Music industry mourns loss of Hayward J. Gregory Jr., founder of Gregota Music LLC, at 74

Virginia Beach, VA – February 22, 2024 ( – Hayward J. Gregory Jr. passed away peacefully on February 14, 2024, at Sentara Princess Anne Hospital in Virginia Beach, VA, surrounded by his loving family. Born on May 23, 1949, to Hayward and Mattie (Holmes) Gregory, natives of Savannah, Hayward’s passion for music ignited at a young age when he began singing in churches and public schools at the tender age of seven.

Throughout his illustrious career, he gained recognition and admiration as an American singer, guitarist, composer, and producer. Under the stage name Haywood Gregory, he shared his remarkable talents with audiences around the world, earning numerous accolades including resolutions from the New Jersey State General Assembly and the New Jersey State Senate, honoring him as a world-class musician and devoted family man.

Hayward’s musical legacy transcended genres, as he collaborated with iconic artists such as Bruce Springsteen, Tony Bennett, BB King, Buddy Guy, The Blind Boys of Alabama, and many others, leaving an indelible mark on all who had the pleasure of hearing his music.

In 1983, Hayward founded Gregota Music LLC, a testament to his entrepreneurial spirit and dedication to nurturing emerging talent in the music industry. Beyond his musical achievements, Hayward’s greatest joy was his family. He shared a lifelong love story with his beloved wife, Emma J. Cuyler-Gregory, whom he met at the age of 12 in Savannah. They were married for 56 years, building a life filled with love, support, and cherished memories. Hayward’s profound faith in God guided his life’s journey, prioritizing his spiritual well-being and the importance of family above all else.

He was preceded in death by his parents, Hayward and Mattie Gregory; his siblings, Hazel Gregory-Smith (William Smith), Dorothy Gregory and Joseph L. Gregory.

Hayward J. Gregory leaves behind a legacy of love and music that will be cherished by his devoted wife, Emma J, Cuyler-Gregory, and their four children: Hayward J. Gregory III (Kathryn Gregory), Lawana M. Gregory Moss (Timothy Moss – Deceased), Latricia Gregory-Thompson (Reginald Thompson), and Jacquelin Gregory Longmire (Kenneth Longmire). Surviving siblings Willie D. Gregory Sr. (Gretta Gregory), Aurelia Gregory-Mitchell, Hilton B. Gregory (Janice Gregory), Michael A. Gregory and a favorite niece Charlene Townes-Dukes.

He also leaves behind 13 grandchildren and 16 great-grandchildren, which were the light of his life, also other relatives and friends.

Hayward J. Gregory Jr. leaves behind a legacy of innovation, passion, and dedication to the music industry. His impact will continue to resonate through his music and the lives he touched. He will be dearly missed by his family, friends, and fans around the world.