While Nightwing is perhaps the purest example of a true hero in the DC Universe who normally wouldn’t show any criminal even the slightest hint of admiration, one comic confirms that Nightwing actually does respect one shocking Gotham villain–a villain that he’s known since he was a child.
Dick Grayson aka Nightwing began his superhero career as Batman’s sidekick, Robin. When he was just a little boy, Dick was a member of the Flying Graysons–a family of acrobatic circus performers–until everything changed when the circus came to Gotham. The Flying Graysons were harassed by members of organized crime in the city, and because they didn’t give into their demands, the Flying Graysons paid with their lives–leaving Dick as the sole survivor. After that tragic event, Bruce Wayne took the child in as his own and raised him to be a crime-fighting superhero. Together, Batman and Robin took on countless rogues like the Joker, Two-Face, and the Riddler–but only one of them earned Dick’s respect, even after he left Gotham to become his own superhero, Nightwing.
In Trinity #12 by Kurt Busiek, Fabian Nicieza, Mike Norton, and Karl Kesel, Superman, Wonder Woman, and Batman (the Trinity) are being attacked by a villain who calls him Enigma as he wishes to overthrow the Trinity and establish his own universal pillars (though the identity of the villain is unknown to the heroes). While the only heroes directly impacted by Enigma’s meddling are Superman, Wonder Woman, and Batman, every hero on Earth is involved in helping them–including Nightwing. However, Nightwing decides that it may take more than every hero’s help to solve this particular mystery, so he calls in a villainous expert at solving puzzles: the Riddler.
Nightwing Hires the Riddler to Solve the Heroes’ Mystery, Proving his Admiration
Nightwing secretly hires Edward Nigma aka the Ridder to solve a chain of robberies–all ancient/magical artifacts–that link back to the overarching mystery plaguing DC’s heroes. This is initially surprising given the amount of brain power and seasoned detectives already working on the case–including Tim Drake who is literally working side-by-side with Nightwing, and (of course) Batman himself. However, Nightwing secretly recruiting Riddler makes total sense when considering one thing: he respects his brilliance.
Riddler is one of the earlier villains in Batman comics, and Dick Grayson saw all of his earliest schemes first-hand throughout his entire childhood, which means that Dick knows exactly how smart the Riddler is from his own life-long experience dealing with the villain. So, while it may seem shocking at first, it actually makes a lot of sense that the one Gotham villain Dick would actually respect is the Riddler–proven true by Nightwing’s willingness to work with him despite the Riddler’s super-villain status.