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Bossman Jack

16:51

BossmanJack arrested

Kiwi tapes

97K views

13:41

Bossman Jack is out of Jail

Biff the Wolfman

11K views

5:59

Bossmanjack First losing Stream after jail -20.000$ - Crying and sad

BossmanJack Rage

9.4K views

42:23

bossmanjack finds god in jail, 50k juicer is fake(doesnt realize it yet),jail story,6k shuffle bonus

IoIshtar

5.3K views

30:59

BossmanJack Wins Over $180,000 In a Single Day, New Record!

Colonel Rat

28K views

40:24

The Crackhead Criminal Gambling His Life Away

Turkey Tom

1.6M views

32:04

bossmanjack QUITS!, why l have no money, gonna go cry, lost 16k this week,not possible on 5 mines

IoIshtar

12K views

25:07

The End of BossmanJack | Rolling The Dice Part 2 - A LolCow Documentary

The Redman

18K views

22:03

Bossmanjack - Speedrunning Losing Millions

SmokeyMcC

99K views

12:26

Rolling The Dice: Inside the World of BossmanJack | Mini-Documentary

The Redman

22K views

11:21

BossmanJack Arrested - Looking at Possibly 5 Years

SmokeyMcC

121K views

35:11

bossmanjack is winning on blackjack, dealers interactions, viewers are mad about ads, 30k withdraw

IoIshtar

2.2K views

8:35

Bossmanjack is now in JAIL

PickleTime

15K views

1:04

Bossman Jack wins 19k then loses it in 2 minutes!

Jonny Hicks

40K views

8:15

NULL UPDATES BOSSMAN JACK, WHAT HAPPENED, AND HIS NEW FAVORITE GAME

TV's Wil Herren

234 views

22:31

BossManJack - Kicks Biggest Gambling Degenerate

BillsYT

112K views

18:21

The Most Degenerate Gambling Streamer | BossmanJack

Nick Nobody

511K views

10:15

BossmanJack Has a Mental Breakdown, Blows up Multiple Keyboards

Colonel Rat

14K views

3:06

BossmanJack is in JAIL! Gone for 5+ Years!

Colonel Rat

50K views

27:23

The Bossman Jack Cycle

Biff the Wolfman

6K views