Bossmanjack's First Stream of 2025

(16:12)

Inside the World of BossmanJack - Rolling The Dice: Part 1 | A LolCow Documentary

(12:26)

bossmanjack is now austingambles, watch this, im the definition of a degen, naggered, its over

(14:30)

BOSSMANJACK IS BACK FROM JAIL LOSES 50K PT 1

(41:43)

The Face of Gambling Addiction - BossmanJack

(29)

Bossmanjack is yet again in JAIL

(9:54)

bossmanjack is a casino b*tch, new sponsor, just need to be smart, why am i doing this to myself?

(28:59)

bossmanjack is the best sponsor to give everything back,shoe collection, theyre laughing when I lose

(21:38)

BOSSMANJACK GETS A NEW SPONSOR PT 1

(17:25)

BOSSMANJACK IS BACK FROM JAIL LOSES 50K PT 6

(26:5)

BossManJack Losing His Father's Money

(13:27)

justinstakes experience of living with bossmanjack for a few days

(1:12:24)

Gambling addict got banned from kick because of this

(1:4)

Degenerate Gambler Losing all His Money.

(1:47)

TRAINWRECKS - THE GREATEST COMEBACK OF ALL TIME! | INSANE WINS AND MAX WINS!!

(12:52)

bossmanjack is in love with a friend on discord,itsok im getting a new refill tomorrow,im ok were ok

(20:49)

How I lost all my money gambling online (Lesson learned)

(4:1econd)

Onlyusemeblade’s Girlfriend Realises She’s Failed In Life While Blade Is Passed Out Behind Her

(44)

1.5M INSANE 1000X HIT ON PLINKO

(33)

The Wise Words of Bossmanjack #1

(10)

The luckiest worst gambler on Earth, Bossmanjack

(17)

BOSSMANJACK IS BACK FROM JAIL LOSES 50K PT 7

(26:37)

Bossmanjack is losing his grip on reality

(27:)

BossmanJack Is Addicted To Losing

(14:41)

Bossmanjack is now back in jail

(8:25)

Has Bossmanjack learned his lesson yet?

(10)

The worst gambler on Earth, Bossmanjack

(18)

BOSSMANJACK IS DEBT FREE!!

(31)

BossmanJack is back and he SCAMMED his viewers!

(19:43)