Winston Alexander Smith (A.K.A. Flags) started his musical career in Montego Bay, Jamaica. He was the lead singer of the band Stepping Stone that consisted of Zoots “Skully” Simms, one of Jamaica’s great precisionist and Eric “Rickenbacker” Frater. From there, Winston went on to play with the band Future Wind and later formed his own band, Ambassan.

He opened for such acts as Eddie Kendricks of the Temptations, Denise Williams and the Trams. He has performed on the same stage as the legendary Bob Marley when he performed at the Jamaica Reggae Sunsplash stage in 1979. Bob Marley is the artist whose sound and style Winston is most likened to. Winston performed a tribute to Bob Marley at Sunsplash in 1981 and performed there again for two more years in 1982 and 1984. In 1984 he left his home in Jamaica to pursue the music scene in the United States.