Kammala wannan jumla: A ranar 1 ga Yuli, 2015, Winnik, a wannan lokacin wanda aka fi so a Toronto, ya koma Maple Leafs, ya sanya hannu a matsayin dan wasa mai 'yanci a kan yarjejeniyar shekara biyu. Ayyukan Winnik na cin zarafi ya ragu daga kakar da ta gabata tare da Maple Leafs, kodayake ya kasance wani ɓangare na ɓangaren kisa. A ranar 28 ga Fabrairu, 2016, a ranar da aka yi ciniki, an yi ciniki da Winnik zuwa Washington Capitals, tare da zaɓaɓɓen zagaye na 5 (Beck Malenstyn) a cikin
2016 daftarin, a musayar ga gaba Brooks Laich, mai tsaron gida mai yiwuwa Connor Carrick da zagaye na 2 na zagaye a 2016 (Carl Grundström).