I te Hōngongoi 1, 2015, i hoki mai a Winnik, i tenei wa he mea tino pai ki Toronto, ki nga Maple Leafs, ka haina hei kaihoko koreutu mo te tau e rua. I heke te mahi whakaeke a Winnik mai i tana wa o mua me nga Maple Leafs, ahakoa he waahanga tuuturu ia mo te whiu whiu. I te Hui-tanguru 28, 2016, i te ahiahi o te wa mutunga o te hokohoko, i hokona a Winnik ki nga Washington Capitals, me te whiringa 5th (Beck Malenstyn) i te kaupapa 2016
, hei utu mo te kaikawe a Brooks Laich, te kaitautoko a Connor Carrick me te 2nd round draft i te tau 2016 (Carl Grundström).