All Videos Channels
  1. Bossmanjack is Back and WINS $45,000

    Bossmanjack is Back and WINS $45,000

    2
    0
    27
    1
  2. Bossmanjack's First Stream of 2025

    Bossmanjack's First Stream of 2025

    2
    0
    61
  3. How did Bossmanjack Get Out of Jail?

    How did Bossmanjack Get Out of Jail?

    67
  5. Bossmanjack is Back and LOSES 45k

    Bossmanjack is Back and LOSES 45k

    2
    0
    36
    1
  6. bossmanjack never wins versus females,my parents have my money,remember ur acoward behind a keyboard

    bossmanjack never wins versus females,my parents have my money,remember ur acoward behind a keyboard

    37
  7. bossmanjack will beable to withdraw that money,look at how happy he gets, hello dallas?oh mrs.yassuo

    bossmanjack will beable to withdraw that money,look at how happy he gets, hello dallas?oh mrs.yassuo

    56
  8. 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?

    72
  9. bossmanjack dont know why hes playing the dumbest games,you wont laugh when i take out fat big money

    bossmanjack dont know why hes playing the dumbest games,you wont laugh when i take out fat big money

    78
  10. this guy gets off watching bossmanjack lose, just take my money bro, im still up 7k this weekim good

    this guy gets off watching bossmanjack lose, just take my money bro, im still up 7k this weekim good

    53
  11. the riggers at chips made bossmanjack go to bed depressed again,its my money buddy,thats rigged dude

    the riggers at chips made bossmanjack go to bed depressed again,its my money buddy,thats rigged dude

    2
    0
    103
  12. bossmanjack know where to get more money,ratdad is concerned if austin relapse,damnthatpawnshop nice

    bossmanjack know where to get more money,ratdad is concerned if austin relapse,damnthatpawnshop nice

    2
    0
    86
  13. 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

    2
    0
    145
    1
  14. 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

    6
    0
    72
  15. 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

    89
    1
  16. bossmanjack plays with raw balance besides the fact that itgot10kin reloads,damn that 2k reload nice

    bossmanjack plays with raw balance besides the fact that itgot10kin reloads,damn that 2k reload nice

    87
  17. 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

    74
  18. bossmanjack is stacking money and he is 100% sober,pos peterson,w car coming in soon,keep on hating

    bossmanjack is stacking money and he is 100% sober,pos peterson,w car coming in soon,keep on hating

    116
  19. 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

    2
    0
    103
  20. 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

    2
    0
    89
  21. 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

    2
    0
    46
  22. 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

    2
    0
    62
  23. 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

    108
  24. 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

    71
  25. 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

    74