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  1. BossmanJack quits Shuffle, loses $10k and gets arrested

    BossmanJack quits Shuffle, loses $10k and gets arrested

    15
  2. 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

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    249
  3. BossmanJack Suicide Baits & Cries & Rages !

    BossmanJack Suicide Baits & Cries & Rages !

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    130
  4. BossmanJack's Gambling Rage: The Ultimate Crackdown

    BossmanJack's Gambling Rage: The Ultimate Crackdown

    169
  5. BossmanJack Rages & Loses 6K ?

    BossmanJack Rages & Loses 6K ?

    158
  6. How did Bossmanjack Get Out of Jail?

    How did Bossmanjack Get Out of Jail?

    67
  7. Bossmanjack's First Stream of 2025

    Bossmanjack's First Stream of 2025

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    107
  8. Bossmanjack is Back and WINS $45,000

    Bossmanjack is Back and WINS $45,000

    2
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    33
    1
  10. Austin_07/BossManJack Black Jack Sesh !

    Austin_07/BossManJack Black Jack Sesh !

    151
    1
  11. BossmanJack After Losing $280K Lost It All

    BossmanJack After Losing $280K Lost It All

    2
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    218
  12. The Bossmanjack Jail Situation is Crazy

    The Bossmanjack Jail Situation is Crazy

    2
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    21
  13. The Bossmanjack Jail Situation just got Worse

    The Bossmanjack Jail Situation just got Worse

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    25
  14. BossmanJack/Austin_07 Rages At Community/Stake !

    BossmanJack/Austin_07 Rages At Community/Stake !

    130
  15. BossmanJack/Austin_07 1300$ Lost Quick !

    BossmanJack/Austin_07 1300$ Lost Quick !

    96
  16. BOSSMANJACK LOSES 63K BANNED FROM TWITCH

    BOSSMANJACK LOSES 63K BANNED FROM TWITCH

    201
  17. BOSSMANJACK RAGES AFTER HIS LOSING $30,000

    BOSSMANJACK RAGES AFTER HIS LOSING $30,000

    90
  18. BossmanJack Tweaks & Rages Out PT 1

    BossmanJack Tweaks & Rages Out PT 1

    121
  19. BOSSMANJACK BUGS RAT DAD ?

    BOSSMANJACK BUGS RAT DAD ?

    66
  20. BossmanJack Tweaks & Rages Out PT 2

    BossmanJack Tweaks & Rages Out PT 2

    102
  21. BOSSMANJACK LOSES -30K MUST WATCH

    BOSSMANJACK LOSES -30K MUST WATCH

    106
  22. BOSSMANJACK RAGES LOSES $30,000

    BOSSMANJACK RAGES LOSES $30,000

    71
  23. BOSSMANJACK LOSING HIS 14K PT1

    BOSSMANJACK LOSING HIS 14K PT1

    75
  24. BOSSMANJACK LOSING HIS 14K PT3

    BOSSMANJACK LOSING HIS 14K PT3

    77
  25. BOSSMANJACK LOSING HIS 14K PT2

    BOSSMANJACK LOSING HIS 14K PT2

    69