Winston Alexander Smith (A.K.A. Flags) was born in St. James, Montego Bay, Jamaica. He grew up in the Canterbury Community and attended the Albion All Age School. He graduated in 1972.
Upon leaving school “Flags” went on to live in the community of Anchovy where he started his musical career. He was the lead singer of the band Stepping Stone, put together by Calvin Clark and consisted of Zoots “Skully” Simms, one of Jamaica’s great percussionist on drums and Eric “Rickabacka” Frater on guitar.
In 1974, the Stepping Stone Band merged into the Future Wind Band, led by Hugh “Bobo Lloyd” Hall playing around Jamaica in some small community night clubs. In 1976 “Flags” family left Anchovy for the community of Flankers where he continued to work with the Future Wind Band which became the resident band for various entities, including The Disco Inferno in Rose Hall, The Great River Tours and The Negril Huts Resort.
While grooming his musical talent, “Flags” opened for house name acts such as Eddie Kendricks of the Temptations, Denise Williams and the Trams to name a few. In the summer of 1979, “Flags” performed on the same stage as the legendary Bob Marley at the Jamaica Reggae Sunsplash. “Flags” sound and style is similar to that of the legendary Bob Marley who is one of his favorite artist. During Reggae Sunsplash of 1981, “Flags” performed a tribute to Bob Marley. In 1982 he formed his own band Ambassan, which was an offshoot of the Future Wind Band and performed at Reggae Sunsplash again for two more years in 1982 and 1984.
In 1984 “Flags” left his home in Jamaica to pursue the music scene in the United States of America. After migrating to Miami, Florida, he joined forces with the reggae band Immortals consisting of Paul “I-Paul” Gauntlette and junior “Yatta” Biggs. A year later, he started working with producer Courtney “Blemo” Crichton, releasing the singles Cool Rudie and Natty Gone Red on Crichton’s Intellitec label. “Flags” also worked with Neville “Prophet Kato” Thompson releasing the song Bossman on the Buffalo label. A remake of Errol Dunkley’s Please Stop Your Lying was also released on the I-Tek label, but it was retitled You’re Gonna Need Me.
“Flags” was diagnosed with glaucoma and for years he struggled to maintain his vision. This he was not able to conquer and for the past ten years he has been visually impaired. His blindness has not stopped his recording career. “Flags” is in the process of completing his first album. The first single Praise Jah in presently available on all digital media platforms.