Gleason akaita mutambo wake wokutanga, semumhanyi mumwe chete weU.S. Virgin Islands, paMitambo yeOlympic yeZhizha ya2000 muSydney. Akakundikana kuenda kumasemifinals mumitambo yake yega yega, achiisa makumi matatu nemapfumbamwe mumakumi maviri emamita akasununguka (1:54.64) uye makumi mana nemaviri mune imwe neimwe yemamita zana akasununguka
(52.00) uye 200 m m mumwe nomumwe (2:08.25).