He has "won" multiple times.
He won a dicking with dudes, which it seems he loves going by his recurring willingless to suck on dick shaped objects without hesitation. :smugnako:
Seems like his "abandonment" of his family may have just been a case of immortals not having a good sense of time.
Dude probably just went out for a walk, and did not take into account how much time had passed.