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Bossmanjack Gambling
18:21
The Most Degenerate Gambling Streamer | BossmanJack
Nick Nobody
537K views
14:23
Bossmanjack wins the most money he ever has. Also, Bossmanjack loses the most money he ever has.
BossManCrack
59K views
1:02
BossmanJack Loses $10,000 in 12.2 Seconds On Limbo
Colonel Rat
98K views
11:51
BossmanJack Wins $23,000. Loses it in 2 Minutes...
Colonel Rat
66K views
11:21
Bossmanjack turns $500 into $21k. But will he lose it all?
BossManCrack
12K views
1:04
Bossman Jack wins 19k then loses it in 2 minutes!
Jonny Hicks
50K views
40:24
The Crackhead Criminal Gambling His Life Away
Turkey Tom
1.8M views
12:57
bossmanjack loses 61k hes offically quitting gambling
Crackmanlive
20K views
13:27
BossManJack Losing His Father's Money
BossManLacks
24K views
8:34
BossmanJack Unbanned From Kick, Loses $15,000 in 2 Minutes
Colonel Rat
58K views
30:59
BossmanJack Wins Over $180,000 In a Single Day, New Record!
Colonel Rat
33K views
15:50
Kick's worst gambling addict: BossmanJack
Kiwi tapes
814K views
13:24
BOSSMANJACK LOSES -30K MUST WATCH
OGClay
10K views
25:07
The End of BossmanJack - Rolling The Dice: Part 2 | A LolCow Documentary
The Redman
22K views
17:34
BossmanJack Lost It All Rages At a Viewer
OGClay
7.4K views
11:29
BossmanJack Cries The Morning After
OGClay
4.3K views
12:26
Inside the World of BossmanJack - Rolling The Dice: Part 1 | A LolCow Documentary
The Redman
24K views
31:15
This one has it all. Bossmanjack wins $14k, calls mom, loses $14k, and more. #gaming #twitch
BossManCrack
143K views
22:31
BossManJack - Kicks Biggest Gambling Degenerate
BillsYT
117K views
1:02
Gambling addict loses $10 000 in 10 seconds (any% speedrun)
debtmanjack
56K views
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