Rubuta ci gaba ga wannan sakin layi - Leonard ya kasance farkon wanda ya cancanci a tsara shi a shekarar 2016
, amma ba a zaɓa ba yayin wasa don Green Bay Gamblers na United Hockey League. Bayan shekaru biyu tare da Gamblers, Leonard ya shiga Jami'ar Massachusetts Amherst ("UMass"), yana wasa da ƙungiyar hockey na kankara, UMass Minutemen yayin karatun Sadarwa da Gudanar da Wasanni. Yayin da yake tare da Minutemen, Leonard ya ja hankalin San Jose Sharks, wanda ya zaɓe shi a zagaye na shida, na 182 a cikin 2018 NHL Entry Draft duk da cewa ba shi da wata hulɗa da Leonard a lokacin aikin da ya gabata. A shekara ta uku a UMass, Leonard ya kasance mai karshe ga Hobey Baker Award kuma ya jagoranci dukkan 'yan wasan NCAA a raga, tare da 27.