Dick Grayson's first night as Nightwing in Chicago, and he's already got SWAT helicopters chasing him. Pretty good start for his Chicago career! But before things go to absolute shit for him, earlier that day, Dick finds himself watching a speech given by Chicago's mayor about closure, etc etc, while dropping some hints about Chicago, IE not having "masks" and some guy named the prankster. While at the press conference, Dick meets up with a photographer named Mike who will be subletting his room, and gets the key from his new roommate. Only problem about the apartment? Right near the train, but Dick finds some use for that...
Cut to: Dick riding on top of the train as Nightwing. See? Use! Elsewhere, a man by the name of Johnny Spade, who is a gambler that deals in information, meets with a union worker, who has just lost a bet, thus has to pay up with some info. Spade knows the guy is lying to him, so he shakes him down a bit, which stirs up the guy's female companion, who goes a bit nuts.
You see, this woman... Thing Smeagol from Lord of the Rings, but sexy! And not a hideous monster... which I guess would come with the sexy, but nevertheless, she talks to herself, a lot. With a knife to Spade's throat, she gets interrupted by a thrown wingding from Nightwing. The woman finds herself very interested in Nightwing, as we know by the fact she tells herself this. Surprisingly, crazy lady throws the wingding back with as much accuracy as Dick threw it, then makes an escape. Dick follows her outside, but she's nowhere to be found.
Spade emerges outside and tells Dick that the woman's name is Mali, and she's somewhat of a "mimic" as he puts it. Turns out Spade was just the man Dick was looking for, as he brings up Zucco to the info dealer, who seems more interested in the fact that there's a masked vigilante in town. Nevertheless, Spade seems to agree to look into things, but this is when the cops show up.
Cops give chase (opening scene) yadda, yadda, yadda, somehow one of the copters starts to go down, but Dick saves the pilots before the crash.
Elsewhere, the Mayor is heading in for the night, and enters his car with an advisor in his ear. Seems the Prankster is a bit of a cyber terrorist, and leaks to them that Spade is snooping around for Zucco in the employ of Nightwing. The advisor suggests to the Mayor that maybe they could find Zucco first, to which the Mayor shrugs off just saying something along the lines of "sure, talk to the commissioner." Buuuuuut, we soon find out that the Mayor knows exactly where Zucco is... and that's driving his car.
Finally, the Prankster makes his debut by putting a child trafficker in one hell of a situation that involves lighting his profits on fire to keep a wolf at bay... dick move on the Prankster's part.