Nyorai kuenderera mberi kwechikamu chino - Musi waChikunguru 1, 2015, Winnik, panguva ino aidiwa nevateveri muToronto, akadzokera kuMaple Leafs, achisaina semunhu akasununguka pachibvumirano chemakore maviri. Kugadzirwa kwaWinnik kwekurwisa kwakaderera kubva mwaka wake wapfuura neMaple Leafs, kunyangwe akaramba ari chikamu chakasimba chechirango chinouraya. Musi waFebruary 28, 2016, musi wekupedzisira wekutengeserana, Winnik akatengeswa kuWashington Capitals, pamwe chete nechisarudzo chechishanu chechishanu (Beck Malenstyn) mu 2016 draft
, mukutsinhana neanotungamira Brooks Laich, tarisiro yemudziviriri Connor Carrick uye 2nd kutenderera dhizaini muna 2016 (Carl Grundström).