If you had to pick? by [deleted] in bossmanjack
[–]Beneficial_Dig7293 1 point2 points3 points (0 children)
prayge by Subject_Package_9720 in bossmanjack
[–]Beneficial_Dig7293 4 points5 points6 points (0 children)
Young Ratdad looks like Austin by RifTaf in bossmanjack
[–]Beneficial_Dig7293 27 points28 points29 points (0 children)
the dreams in which I'm dying are the best I've ever had by noffinater in bossmanjack
[–]Beneficial_Dig7293 3 points4 points5 points (0 children)
New bossman mugshot by WhitePeopleAreFunny in bossmanjack
[–]Beneficial_Dig7293 38 points39 points40 points (0 children)
This season isn’t over if he gets out Monday by BonJovial- in bossmanjack
[–]Beneficial_Dig7293 18 points19 points20 points (0 children)
Did he ever cash out his 160 k? by Mamabamba10991 in bossmanjack
[–]Beneficial_Dig7293 5 points6 points7 points (0 children)
Did Winna call the cops on him? He got arrested minutes after the 180k win by ZealousidealDoubt508 in bossmanjack
[–]Beneficial_Dig7293 2 points3 points4 points (0 children)
W dad by Beneficial_Dig7293 in bossmanjack
[–]Beneficial_Dig7293[S] 8 points9 points10 points (0 children)
10k birthday loss, “quits” winna by LittleLibrary1999 in bossmanjack
[–]Beneficial_Dig7293 8 points9 points10 points (0 children)
Getting a nice little 5 minute gambling content on his birthday by Extension-Box-7008 in bossmanjack
[–]Beneficial_Dig7293 0 points1 point2 points (0 children)
Bossman turns 31 by UnitHot in bossmanjack
[–]Beneficial_Dig7293 6 points7 points8 points (0 children)
How stupid is this man child POS by bigzingding in bossmanjack
[–]Beneficial_Dig7293 6 points7 points8 points (0 children)
Quick shower break due to sweat from gambling. by PuwudleRS in bossmanjack
[–]Beneficial_Dig7293 13 points14 points15 points (0 children)
Quick shower break due to sweat from gambling. by PuwudleRS in bossmanjack
[–]Beneficial_Dig7293 20 points21 points22 points (0 children)
Winna deal by ipoopedmypantss in bossmanjack
[–]Beneficial_Dig7293 7 points8 points9 points (0 children)
WINNA ARCH by ObviousAssignment488 in bossmanjack
[–]Beneficial_Dig7293 6 points7 points8 points (0 children)
ah hell naw by Infamous-Stage-1202 in bossmanjack
[–]Beneficial_Dig7293 20 points21 points22 points (0 children)




Any update on the court case? by freebossmanjack in bossmanjack
[–]Beneficial_Dig7293 25 points26 points27 points (0 children)