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Bossmanjack

11:21

BossmanJack Arrested - Looking at Possibly 5 Years

SmokeyMcC

45K views

9:51

Lawyer on BossmanJack Gambling Addiction Lands Him in Jail | 2 Charges

LUS

722 views

7:51

I TRIED BOSSMANJACK GAMBLING STRATEGY ON STAKE!

Sketchy

4K views

10:15

BossmanJack Has a Mental Breakdown, Blows up Multiple Keyboards

Colonel Rat

9.6K views

9:07

BossmanJack is losing it

PickleTime

7K views

8:35

Bossmanjack got sent to JAIL

PickleTime

7.9K views

1:02

BossmanJack Loses $10,000 in 12.2 Seconds On Limbo

Colonel Rat

79K views

18:21

The Most Degenerate Gambling Streamer | BossmanJack

Nick Nobody

506K views

1:01

Bossmanjack quitting shuffle new sponsor inbound

Crackmanlive

914 views

14:23

Bossmanjack wins the most money he ever has. Also, Bossmanjack loses the most money he ever has.

BossManCrack

53K views

12:27

BossmanJack Celebrates Sobriety by Losing Tens of Thousands!

Colonel Rat

16K views

30:59

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

Colonel Rat

22K views

24:39

bossmanjack spotted bigfoot, austin's brother shows up, tongueragex3, RIGGED,why you ban the juicer?

IoIshtar

3K views

3:06

BossmanJack is in JAIL! Gone for 5+ Years!

Colonel Rat

36K views

15:50

Kick's worst gambling addict: BossmanJack

Kiwi tapes

768K views

10:49

bossmanjack let inner demons win again

Crackmanlive

2.2K views

17:58

bossmanjack is done again with this bs website and is doing it, 3200-15k-0, l never win anymore

IoIshtar

4.9K views

25:13

bossmanjack is a weirdo,topmod nicofiend is a rat,confused about stockmarket,that just the way it is

IoIshtar

3.7K views

9:21

bossmanjack falls of the rails!

Crackmanlive

3.5K views

42:55

bossmanjack have a crying sesh,second keyboard slammed,SCAM AND RIGGED,more twitch ads for non subs

IoIshtar

5.6K views