▁director ▁of ▁the ▁DE O . ▁ ▁Jer emy ▁Jordan ▁as ▁W ins low ▁" W inn " ▁Sch ott ▁Jr . ▁/ ▁To yman ▁( se asons ▁ 1 – 3 ; ▁guest ▁season ▁ 5 ): A ▁te ch ▁expert ▁who ▁worked ▁alongside ▁K ara ▁at ▁Cat Co , ▁he ▁is ▁K ara ' s ▁best ▁friend ▁and ▁serves ▁as ▁one ▁of ▁her ▁al lies , ▁helping ▁her ▁develop ▁her ▁cost ume ▁and ▁a iding ▁her ▁in ▁her ▁advent ures . ▁W inn ▁has ▁un re qu ited ▁feelings ▁for ▁K ara ▁and ▁is ▁a ▁rival ▁with ▁James ▁for ▁her ▁affection . ▁However , ▁at ▁the ▁end ▁of ▁" For ▁the ▁Girl ▁Who ▁Has ▁Everything ", ▁W inn ▁has ▁accepted ▁that ▁it ▁is ▁best ▁that ▁they ▁remain ▁as ▁best ▁friends , ▁and ▁in ▁" Sol itude ", ▁he ▁begins ▁seeing ▁Cat ▁Grant ' s ▁new ▁assistant , ▁who ▁is ▁also ▁K ara ' s ▁rival ; ▁S io b han ▁S my the , ▁who ▁is ▁subsequently ▁fired ▁by ▁Cat ▁and ▁who , ▁in ▁" World s ▁Fin est ", ▁becomes ▁a ▁super natural ▁met ah uman ▁super villa in ▁called ▁Silver ▁B ans he e . ▁In ▁the ▁series , ▁he ▁is ▁the ▁son ▁of ▁To yman . ▁Cat ▁nick names ▁him ▁To yman ▁Junior ▁after ▁she ▁finds ▁out . ▁In ▁season ▁two , ▁W inn ▁left ▁Cat Co ▁to ▁work ▁at ▁the ▁DE O ▁as ▁a ▁des k ▁agent . ▁He ▁also ▁works ▁with ▁James ▁O ls en ▁as