Right. Forgot about Donna.
Yeah I know about that one, and... correct me if I'm wrong, both times that he's involved with espionage mission or mission that's considered unclean unlike classic superheroic... well, three times if you count Renegade... someone always says he's too nice to fit into that world.
In Outsiders, it was Batman who tells Dick to fight the good fight and leave the grey area to them. In Renegade, Deathstroke never believes Dick turns around. In Grayson, it was Helena and Midnighter, maybe Tiger King too.
I don't know about Young Justice.
Yeah... he leads the only spy book at that time. SHADE and Grifter were already canceled long before that, now Max Lord is in custody and Leviathan decimated the whole spy world.
No... wait... I forget... Max Lord is Wonder Woman villain now so we can forget about that part too