Every hand played triggered the Boss Blind Ability of The Tooth. Lose $1 per card played.
But Matador doesn't trigger at all. You don't gain $8 for your hand triggering the Boss Blind Ability.
#Matador doesn't work with The Tooth
gray dew
lament turtle
gray dew
It would be an interesting economy Joker to use early to start scaling, or to swap in before a particularly easily triggered Boss Blind, etc. But if it doesn't trigger with every or even most Boss Blinds, then it is not very useful.
But more importantly, either it's a description is incorrect, or it is bugged ie it simply does not work.