[quote=DrewVonAwesome]
Should Nightwing know? I can see it either way.Also I'm going to go ahead and redo the opening post, so disregard everything Pit related unless someone takes him over. Also I need to bug Rin and Gowi to post.I can't wait until when Nightwing gives Howard the ultimate reality check. I'm sure Nightwing has known about the guy for years being in the same position of super rich kid, but isn't a gigantic dick.
[/quote]

Let's face it, Batman would totally know. He probably would have figured it the moment Bucky surfaced as the Winter Soldier. That means Nightwing could either have learned it from Bats, or he could just suspect it.

If you wanted to somehow figure out a way for him and James to have known each other in their Bucky and Robin days, then James would probably have told him himself. 

But that would make Nightwing obscenely old.