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The winner will be revealed on Jan. 28. The winner will be eligible for Florida Teacher of the Year, which will be announced this spring.. UMATILLA When Josh Wintersdorf was summoned from his classroom on Wednesday morning, the algebra teacher at Umatilla Middle School was expecting to see sheriff s deputies. At least that s what Principal Brent Frazier told him. The truth became apparent when Wintersdorf walked outside and was greeted by a sea of unfamiliar faces, all waiting to congratulate him on being one of three finalists for Lake County Teacher of the Year. If you enjoy making people happy and helping people, the best chance you have is to become a teacher, said Wintersdorf, 32. ....