I’m a firm believer in the fact that Star Platinum brought Jotaro all those things while he was in jail because he was trying to get Jotaro to like him. Like “hey I’m sorry I scared you by protecting you from those guys. Please take these magazines and radio and beer I’m not evil I promise.”
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If Jotaro could hide hardback books in his coat and hat to protect himself from Dio's knives, I'm pretty sure he can carry around a can of Raid as well.
Reference under the cut
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His cap got stolen (again)
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being jotaro kujo must have been insane. you are 17 years old. one day you wake up and a purple ghost is haunting you. all it does is punch people and get you beer. you lock yourself into jail. all the prisoners are scared of you. your xenophobic american grandpa shows up with his psychic egyptian friend and tells you you need to kill your bisexual vampire half-great-grunkle to save your mother. suddenly, you're on the worst road trip in the history of mankind with a frenchman, a dog, an autistic nerd, a psychic, and your xenophobic grandpa with a metal hand. you have to fight an orangutan, a cowboy, a baby, a falcon, and the sun, all in the span of 60 days. all of your friends die
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