Gary knew that the smart thing would be to keep on watching, waiting for both sides to weaken each other further, so he could snoop in and finish off the losing side. This way he wouldn’t use a lot of Energy, while still being able to get some Exp.
However, he had decided to take some risks. Given the content of the Quest, it seemed wiser to get involved in the fight before any surprising backup could arrive. He didn’t know how long this gang war would last since it was just a matter of time that the Underdogs would send out their muscle.
If he waited too long the gang war might escalate to the point it would be too dangerous for him to get involved. At the moment, Gary was dressed in all black, so the only colour gang he could help out and pretend to be a part of was the black colour gang.