Ku qor sii wadida sadarkan - Kaliya 16 maalmood ka dib markii Jackson ay sii daayeen Royals, Chicago White Sox waxay u soo bandhigeen heshiis seddex sano ah, oo dammaanad qaadaya $ 700,000 xilli ciyaareedkiiba oo leh kor u kac ku saleysan waxqabadka $ 8.15 milyan muddadaas. Mid ka mid ah milkiilayaasha White Sox Jerry Reinsdorf ayaa sheegay inaysan filaynin inuu ciyaari doono xilli ciyaareedka oo dhan inta uu ka hadlayo arrimaha miskaha iyo necrosis avascular. Jackson wuxuu ciyaaray laba xilli ciyaareed isagoo ka soo muuqday 23 kulan 1991 iyo 85 kulan 1993. Wuxuu ka soo muuqday liiska naafada ee White Sox xilli ciyaareedkii 1992 sababtoo ah wuxuu dhammeystirey qalliin beddelashada miskaha horaantii sanadkaas. Waxa uu ahaa White Sox in uu sameeyay muuqaalkiisa kaliya ee xilli ciyaareedka dambe, 1993 American League Championship Series
, kaas oo ay Chicago ka badiyeen Toronto Blue Jays lix kulan.