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.