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Winter was born and grew up in Seminole, Florida. He was a graduate of Seminole High School. Winter was a Bachelor of Arts graduate in weather at the University of Kansas. He started his job as a television weather man at KGBT-TV in Harlingen, Texas. Winter worked there for two years before he moved near Tampa in 1994. It was in Tampa that he started working for WFLA-TV. He was most often the morning meteorologist for WFLA-TV but he sometimes would make the evening reports. Winter held the "Seal of Approval" from the American Meteorological Society.
As well as being a weather man, Winter also owned the company "Big U Media" with a friend who also worked at WFLA-TV. Big U Media was an advertising company. He was also a member of a local charitable organization and Mardi Gras krewe, The Rough Riders. They helped underprivileged and sick children by giving teddy bears at homeless shelters and in hospitals.
On April 5, 2007, the police got a telephone call from an unknown person about problems at Winter's home. While the deputies pounded on his front door of his home in the Tealside section of Lithia, Winter shot himself. He died very quickly. His death was a surprise to the people who worked with him and viewers. He had left the WFLA after a newscast the night before cheerful and upbeat in mood. It was learned that he suffered from severe depression.