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The First of Four Children, born in Sangre Grande, Trinidad , Sherwin Rogers better known as the Postman started his entertainment career at the early age of eight when he placed first in a dance competition at his elementary school. While he spent most of his teenage years in the church, he always involved himself in activities that would allow him to entertain others, and this led to his reputation as one of North Eastern College 's most talented students, as well as a definite stage favorite. He was without a doubt North Eastern's most respected calypsonian, and won the school's calypso competition for three consecutive years. Sherwin was so loved by his classmates and teachers that he was allowed to attend classes for an additional year even though academically he was not qualified to do so.

On a major competition level, Postman's resume is quite an impressive one. He entered the National Junior Calypso Monarch Competition, placed third in the NJAC Calypso Competition, and eight in the C.D.C. competition.

In December 1987 Sherwin migrated to the US to live with his father, who was instantly aware of his sons talent and sought to further develop it with the help of a family friend who was a calypso composer. Postman recorded two of his songs but was totally unsatisfied, not to mention discouraged by the poor quality of the production and decided in 1988 to change his course and enrolled in the US Army.

While in the Army, Sherwin entered a star search, and to his delight won the contest. In 1992 he then left the military and continued to sing for friends and family for the next ten years.

In 2002 a co-worker at the US Post Office where he has worked for the past nine years (hence his stage name “Postman”), encouraged Sherwin to do a recording since he felt he had a great voice. But there was one problem. Sherwin was not a Writer and had none of his own material.

However, filled with ambition and the love for calypso, in October 2002, Sherwin put himself to the test and wrote ten songs in two weeks. By the third week he had recorded a song called “Riot”, and have since recorded five other songs.

Since then, Postman has become one of Brooklyn 's elite performers. He has done numerous shows at arenas like The Elite Ark, Soca Arena, Club Carib, as well as house parties and backyard parties in the Brooklyn area. In 2003 Postman Participated in New York 's Soca Monarch Placing 4th.This artist is certainly one to watch as he continues to mature in his field. Postman claims, “ I enjoy entertaining and love to be on stage”.