The moment DC officially confirmed Nightwing surpassed Batman
Batman taught his guards several skills, but one valuable lesson Nightwing learned allowed him to rise above the Dark Knight (according to Bruce).
Of all of Batman's sidekicks, Nightwing was always the one most likely to overtake the Caped Crusader, and Bruce himself was able to pinpoint exactly when that happened. Dick Grayson has been by Bruce Wayne's side almost from the beginning, so it's only natural that he would one day surpass his mentor.
Remember that the word "beyond" means different things to different people. Beyond Batman doesn't necessarily mean Dick Grayson will be the Hood's eventual heir. After all, during Grant Morrison's run, he did temporarily acquire Bruce's hood, and throughout, Dick made it clear how eager he was to get rid of it. In the process of renaming himself Nightwing from Robin, he worked so hard to escape Batman's shadow that he had no intention of going back. Transcendent doesn't even necessarily mean that Nightwing has surpassed Batman as a fighter, though that's debatable. Outsmarting Batman is as easy as understanding his true calling. And in The Dark Knight's own mind, Dick did just that.
Justice League #0, created by Brad Meltzer with a team of artists, retraces the Justice League An annual look back from the day Batman, Superman, and Wonder Woman first began developing a plan for team success. A page illustrated by J.H. Williams recalls the day of Donna Troy and Terry Long's wedding, with Bruce Wayne chatting with his former guardian. He expressed how proud Dick was of forming the Titans, calling them his friends. Dick corrects him, calling them his family, following a piece of advice he told Dick a long time ago. When Bruce says to Wonder Woman, "He surpassed me," he has a look of surprise and gloom on his face, but admittedly delighted.
Nightwing Understands Batman's Mission Better Than Anyone
To understand what Batman means by "beyond" in this context, one must understand the core of Batman's mission. Batman does what he does so that no one is forced to live with the trauma he went through when he lost his parents, and no one feels alone with the burden. This is part of the reason he has acquired many assistants over the years. They weren't just crime-fighting partners; they were the family he'd found.
He puts his companions through rigorous mental and physical training, but none of the skills Batman teaches seem to match More valuable than a moral lesson about the importance of starting a family. Dick Grayson learned this lesson when he created the Titans. Like Batman before him, Nightwing recruited a team of heroes who weren't just competent heroes he could call sidekicks or friends, but his family. This is what a hero needs to succeed: not teammates, not even friends, but the compassion and care of family (whether biological or otherwise) to help them see the light at the end of the tunnel. Bruce found his family when he met Dick and let the family grow. Now, Nightwing has done the same to the Titans, continuing the legacy Batman started for him in many ways.
