In the DC Universe, Red Hood have had a tumultuous relationship, and one bit of advice made with the best intentions might have did more harm than good.
Even before he met Bruce Wayne, Jason Todd had a difficult life filled with crime and drugs. That was probably why Batman decided to take him under his wing and guide Jason's anger towards doing good as Robin. But it was obvious from the start that Jason would be a very different Boy Wonder than Dick Grayson. Jason's fighting style, prone to brutal violence and recklessness, would ultimately lead him towards an untimely death at the hands of the Joker.
Eventually, Jason would be resurrected as the murderous antihero Red Hood. His anger and violence was now channeled full force into killing bad guys, which is contrary to Batman's philosophy on murder. In a flashback to his Robin days, which took place in Red Hood and the Outlaws #1 by Scott Lobdell and Dexter Soy, Jason recalls how Batman told him never to cross the line into becoming a murderer. "...If you cross that line...there's not turning back...you'll be no better than they are." Years later as Red Hood tries to soften his approach, he tries to embrace Batman's words, but it's harder than he would like to believe.
The truth is that Batman's words of wisdom can be misconstrued. They were meant to try and help Jason and bring him back from the brink of becoming an angry and vengeful person. But the meaning behind the advice can be looked at from a different perspective. Since Jason has already committed murder as the Red Hood, the line there is no coming back from that Batman had warned Jason about has already been crossed. Since the Red Hood has already taken that step into becoming a murderer there is no point trying to redeem himself because, as Batman put it, there is no redemption.
Batman's heart was in the right place, but this just goes to show that psychologically helping young children, especially troubled ones, is just beyond his specialty. He can teach them to harness their anger into becoming strong fighters, as he has done with Jason and all the other Robins. But where Batman falls short is in combining the physical side of being a vigilante with the moral side. As a young boy, Bruce Wayne learned about loss and trauma. But every traumatic childhood is different. He was ill-equipped to help Jason recover from his. And so by trying to teach him, Batman actually drove the Red Hood deeper into becoming a killer.
