So CH3 is activating and o,p directing by an inductive effect.
Br is deactivating (inductive) but o,p directing by a resonance effect.
We generally think that when two directing influences are in conflict, the more activating group "wins" the directing struggle. Here, both Br and -CH3 are o,p; but since they are ortho, they direct to different locations. CH3 is more activating - but Br is directing by the stronger effect, resonance. So this is a very subtle case.
In reality, I wouldn't be surprised to see a significant mixture of the two types of products.