Bossman Jack

Bossmanjack is BACK! 25:26
Bossmanjack is BACK! PickleTime 18,570 4 дня назад
The Most Degenerate Gambling Streamer | BossmanJack 18:21
The Most Degenerate Gambling Streamer | BossmanJack Nick Nobody 1,922,620 1 год назад
Inside the World of BossmanJack - Rolling The Dice: Part 1 | A LolCow Documentary 12:26
Inside the World of BossmanJack - Rolling The Dice: Part 1 | A LolCow Documentary The Redman 46,320 1 год назад
The End of BossmanJack - Rolling The Dice: Part 2 | A LolCow Documentary 25:07
The End of BossmanJack - Rolling The Dice: Part 2 | A LolCow Documentary The Redman 96,480 11 месяцев назад
Kicks worst gambling addict gets worse - Bossman jack 16:51
Kicks worst gambling addict gets worse - Bossman jack Kiwi tapes 411,179 11 месяцев назад
Bossmanjack - Speedrunning Losing Millions 22:03
Bossmanjack - Speedrunning Losing Millions SmokeyMcC 274,895 11 месяцев назад
The Horrifying Life of a Professional Gambling Addict 05:28:56
The Horrifying Life of a Professional Gambling Addict Turkey Tom 1,594,430 1 месяц назад
BossmanJack actually WINS 185k 28:16
BossmanJack actually WINS 185k PickleTime 503,261 11 месяцев назад
BOSSMANJACK IS OK NOW 17:43
BOSSMANJACK IS OK NOW OGClay 208 1 день назад
The Crackhead Criminal Gambling His Life Away 40:24
The Crackhead Criminal Gambling His Life Away Turkey Tom 3,088,913 1 год назад
How to LOSE $30,000 by bossmanjack 00:46
How to LOSE $30,000 by bossmanjack PickleTime 306,724 11 месяцев назад
The Face of Gambling Addiction - BossmanJack 00:29
The Face of Gambling Addiction - BossmanJack PickleTime 135,935 9 месяцев назад
Bossman jack HITS BIG? 00:14
Bossman jack HITS BIG? GambaClips 11,995 7 месяцев назад
bossmanjack loses $10,000 in 12 seconds... #bossman #gambling #onlinegambling #rage #blackjack 00:21
bossmanjack loses $10,000 in 12 seconds... #bossman #gambling #onlinegambling #rage #blackjack BossManRats 4,163 4 месяца назад
Kino Casino: Bossman Jack Arrested (July 5, 2024) 24:41
Kino Casino: Bossman Jack Arrested (July 5, 2024) elissa clips 1,875 11 месяцев назад
Bossmanjack is losing his grip on reality 27:00
Bossmanjack is losing his grip on reality PickleTime 93,246 9 месяцев назад
The Wise Words of Bossmanjack #1 00:10
The Wise Words of Bossmanjack #1 PickleTime 60,457 9 месяцев назад
How bossmanjack lost 200k - Part 4 Finale 41:57
How bossmanjack lost 200k - Part 4 Finale PickleTime 143,057 10 месяцев назад
Bossman Jack's gambling transition 00:38
Bossman Jack's gambling transition GUTS 1,805 1 год назад
Bossman Jack's destructive rage 00:18
Bossman Jack's destructive rage GUTS 1,474 1 год назад

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