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  1. BossmanJack's Gambling Rage: The Ultimate Crackdown

    BossmanJack's Gambling Rage: The Ultimate Crackdown

    220
  2. BossmanJack Suicide Baits & Cries & Rages !

    BossmanJack Suicide Baits & Cries & Rages !

    2
    0
    170
  3. BossmanJack Rages & Loses 6K ?

    BossmanJack Rages & Loses 6K ?

    193
  4. bossmanjack just got a max win, history repeat itself, 15k withdraw total, you can sub to talk shit

    bossmanjack just got a max win, history repeat itself, 15k withdraw total, you can sub to talk shit

    3
    0
    266
  5. Bossmanjack's First Stream of 2025

    Bossmanjack's First Stream of 2025

    2
    0
    305
  6. BossmanJack After Losing $280K Lost It All

    BossmanJack After Losing $280K Lost It All

    2
    0
    271
  7. Bossmanjack is Back and WINS $45,000

    Bossmanjack is Back and WINS $45,000

    2
    0
    38
    1
  8. BOSSMANJACK GETS JUICED BY RAINBET PT2

    BOSSMANJACK GETS JUICED BY RAINBET PT2

    77
  9. BOSSMANJACK RAGES AFTER HIS LOSING $30,000

    BOSSMANJACK RAGES AFTER HIS LOSING $30,000

    97
  10. BOSSMANJACK LOSING HIS 14K PT3

    BOSSMANJACK LOSING HIS 14K PT3

    78
  11. BOSSMANJACK GETS JUICED BY RAINBET ?

    BOSSMANJACK GETS JUICED BY RAINBET ?

    75
  12. BOSSMANJACK BUGS RAT DAD ?

    BOSSMANJACK BUGS RAT DAD ?

    67
  13. The BossmanJack from Latvia - PapaonWing

    The BossmanJack from Latvia - PapaonWing

    14
  14. BOSSMANJACK GETS JUICED BY RAINBET PT3

    BOSSMANJACK GETS JUICED BY RAINBET PT3

    78
  15. BOSSMANJACK RAGES LOSES $30,000

    BOSSMANJACK RAGES LOSES $30,000

    71
  16. BOSSMANJACK LOSING HIS 14K PT1

    BOSSMANJACK LOSING HIS 14K PT1

    75
  17. BOSSMANJACK LOSING HIS 14K PT2

    BOSSMANJACK LOSING HIS 14K PT2

    69
  18. BOSSMANJACK MAKES IT RAIN ?

    BOSSMANJACK MAKES IT RAIN ?

    58
  19. BOSSMANJACK Wins $4000 ?

    BOSSMANJACK Wins $4000 ?

    61
  20. bossmanjack's pc has a virus so he unplugged it, voice call moment, do not click links,garage stream

    bossmanjack's pc has a virus so he unplugged it, voice call moment, do not click links,garage stream

    9
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    1.16K
    8
  23. bossmanjack wants to f a dude, it turns off and on out of nowhere, -40k on howl

    bossmanjack wants to f a dude, it turns off and on out of nowhere, -40k on howl

    187
  24. Bossmanjack is Back and LOSES 45k

    Bossmanjack is Back and LOSES 45k

    2
    0
    45
    1
  25. The Bossmanjack Jail Leak Situation is Crazy

    The Bossmanjack Jail Leak Situation is Crazy

    44
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