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I'm not 100% sure but I believe that among active rappers it is a tie between Gucci Mane and Lil Boosie. If you count Diddy as an "active rapper" he's up there too. Then there's a new underground rapper T Pacheco that's been arrested 50 plus times. He's from Santa Rosa CA West Ninth District, which is located in Northern Bay Area.

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Q: What American rapper has been arrested the most?
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