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  1. Bossmanjack is Back and WINS $45,000

    Bossmanjack is Back and WINS $45,000

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  2. Bossmanjack's First Stream of 2025

    Bossmanjack's First Stream of 2025

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  3. Bossmanjack is Back and LOSES 45k

    Bossmanjack is Back and LOSES 45k

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  5. How did Bossmanjack Get Out of Jail?

    How did Bossmanjack Get Out of Jail?

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  6. bossmanjack QUITS gambling,its real sponsored money, weird dealer, its all gone,l have no money dude

    bossmanjack QUITS gambling,its real sponsored money, weird dealer, its all gone,l have no money dude

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  7. bossmanjack loses everything on the originals, its all raw,a lot of people came from the hate videos

    bossmanjack loses everything on the originals, its all raw,a lot of people came from the hate videos

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  8. the riggers at chips watch bossmanjack lose and get off on it, i need another deal, lets go play rs

    the riggers at chips watch bossmanjack lose and get off on it, i need another deal, lets go play rs

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  9. bossmanjack is changing the way hes gambling, lets go all in here, respect me and i dont ban you

    bossmanjack is changing the way hes gambling, lets go all in here, respect me and i dont ban you

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  10. the riggers at chips and shuffle dont want bossmanjack to win,car funds gone, have a good night guys

    the riggers at chips and shuffle dont want bossmanjack to win,car funds gone, have a good night guys

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  11. bossmanjack wants dallas to get on the mic,dont be scared,why arent you answering? chips maintenance

    bossmanjack wants dallas to get on the mic,dont be scared,why arent you answering? chips maintenance

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  12. bossmanjack is not losing ever again and there nothing you can do about it,im totally clean,cocacola

    bossmanjack is not losing ever again and there nothing you can do about it,im totally clean,cocacola

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  13. bossmanjack lost it all but it doesnt mean he is not getting better, cant pay taxes, i deserve money

    bossmanjack lost it all but it doesnt mean he is not getting better, cant pay taxes, i deserve money

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  14. bossmanjack just donated the rest of his wallet to the riggers at rainbet,cheating,give my xrp buddy

    bossmanjack just donated the rest of his wallet to the riggers at rainbet,cheating,give my xrp buddy

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  15. bossmanjack is praying that you seek help,im not cracked out im sober,i dont bully,seek peace within

    bossmanjack is praying that you seek help,im not cracked out im sober,i dont bully,seek peace within

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  16. bossmanjack is gonna show you self-restrain on friday originals, one more last one, keep on watching

    bossmanjack is gonna show you self-restrain on friday originals, one more last one, keep on watching

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  17. bossmanjack is DONE donating to the riggers at chips,WHY?!, great thing i got going here, real money

    bossmanjack is DONE donating to the riggers at chips,WHY?!, great thing i got going here, real money

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  18. bossmanjack is in love with a friend on discord,itsok im getting a new refill tomorrow,im ok were ok

    bossmanjack is in love with a friend on discord,itsok im getting a new refill tomorrow,im ok were ok

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  19. bossmanjack wants you to figure it out,taxes, ill put in my last money,oh mrs. dallas oh mrs. dallas

    bossmanjack wants you to figure it out,taxes, ill put in my last money,oh mrs. dallas oh mrs. dallas

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  20. bossmanjack got disrespected by dallas,I got baited again,l thought this discord was for friendsonly

    bossmanjack got disrespected by dallas,I got baited again,l thought this discord was for friendsonly

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  21. bossmanjack needs to get out and get a girl, looking for a juicer, were ok were ok, is dallas here?

    bossmanjack needs to get out and get a girl, looking for a juicer, were ok were ok, is dallas here?

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  22. bossmanjack want to get back to his old ways,we need to get that car,everything magic you happy now?

    bossmanjack want to get back to his old ways,we need to get that car,everything magic you happy now?

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  23. bossmanjack is back with chips, d**n that wager race nice,w for dallas in the chat,chips is the goat

    bossmanjack is back with chips, d**n that wager race nice,w for dallas in the chat,chips is the goat

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  24. bossmanjack is not respected by dallas,getting hacked,no sponsor talk, dallas its chips time brother

    bossmanjack is not respected by dallas,getting hacked,no sponsor talk, dallas its chips time brother

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  25. bossmanjack is going to dice in your wildest dreams,im cashing out,keepon watching everyday buddyboy

    bossmanjack is going to dice in your wildest dreams,im cashing out,keepon watching everyday buddyboy

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