The most legitimate way to make this trope work is by making the rogue a Justified Criminal who steals only to survive in an uncaring world that leaves him with no other option, especially if the laws are unfair and benefit a select few at the expense of others, including the rogue. For extra points, he may even give some of his takings to the poor. It helps that none of their victims are anyone we know or that they've made sure the audience knew they were jerks, which makes it "okay" to steal from them.
A person who breaks the law, for their own personal profit, but is nice enough and charming enough to allow the audience to root for them, especially if they don't kill or otherwise seriously harm anyone.
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