Nyorai kupfuurira kweiyi ndima - Leonard pakutanga akanga ari wokutanga akakodzera kunyorwa muna 2016
, asi haana kusarudzwa achitamba neGreen Bay Gamblers yeUnited States Hockey League. Mushure memakore maviri neGamblers, Leonard akabatana neYunivhesiti yeMassachusetts Amherst ("UMass"), achitamba timu yavo yehockey yechando, iyo UMass Minutemen achidzidza Kutaurirana uye Sport Management. Paaive neMinutemen, Leonard akabata kutariswa kweSan Jose Sharks, avo vakamunyora mumutambo wechitanhatu, 182nd yakazara mu2018 NHL Entry Draft kunyangwe asina kuonana naLeonard panguva yekugadziriswa. Mugore rake rechitatu kuUMass, Leonard aive mumhedzisiro yeHobby Baker Award uye akatungamira vese vatambi veNCAA muzvinangwa, aine makumi maviri neshanu.