Ku buuxi weedha soo socota:
2016, laakiin looma dooran markii uu u ciyaarayay Green Bay Gamblers ee Horyaalka Hockey-ga Mareykanka. Kadib laba sano oo uu la joogay Gamblers, Leonard wuxuu ku biiray Jaamacadda Massachusetts Amherst ("UMass"), isagoo u ciyaaray kooxdooda hockey-ga barafka, UMass Minutemen isagoo baranaya Isgaarsiinta iyo Maareynta Ciyaaraha. Intii uu la joogay Minutemen, Leonard wuxuu soo jiitay dareenka San Jose Sharks, oo u qortay wareegga lixaad, 182aad guud ahaan 2018 NHL Entry Draft inkasta oo uusan wax xiriir ah la lahayn Leonard inta lagu gudajiray howsha hordhaca ah. Sanadkiisii saddexaad ee UMass, Leonard wuxuu final u ahaa Abaalmarinta Hobey Baker wuxuuna hogaamiyay dhamaan ciyaartoyda NCAA goolal, 27.