Batman has had a mixed legacy with sidekicks, raising Dick Grayson to become the heroic Red Hood. However, before Jason Todd returned to Gotham and began slaughtering its criminals, another killer sidekick sullied the Bat-Family's good name. This time, however, it was Dick Grayson's charge who attempted to become a lethal protector.

Thaddeus Ryerstad was an orphan, or so he claimed. He grew up on saved by the real Nightwing, who agreed to take him under his tutelage and train him, as Batman had done for Dick.

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Nightwing Had His Own Jason Todd

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Nite-Wing was first introduced in Nightwing #8, by Chuck Dixon and Scott McDaniel, and being that it was 1997, the era of the extreme 90s anti-hero had not yet run its course. Tad was crafted in that morally gray model, and he often violently attacked those he perceived as a threat, even when they were not. His modus operandi was similar to Red Hood, the revived second Robin with a chip on his shoulder and two guns in his holster. However, where Jason Todd was partially redeemed and brought back into the Bat-Family after his time as a killer, Nite-Wing enjoyed killing too much to stop.

Dick believed he could help the boy by training him and giving him focus for his anger and feelings of inadequacy - as Batman had for him. Unfortunately, Nightwing underestimated the kids’ mean streak and the depth of resentment that Tad was harboring. The training did not result in Nite-Wing becoming a more moral or upright hero, but just a more effective bully. Eventually, Tad ran afoul of an undercover cop and killed him. Nightwing was forced to it that he had failed his first ever sidekick and convinced Tad to turn himself in to the authorities, who promptly arrested him.

Nightwing's Failed Sidekick Changed How He Saw Batman

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Though Dick’s first attempt at mentorship was a failure, it may have given him a deeper appreciation of his own former mentor. Raising sidekicks is not easy and what Dick went through with Nite-Wing was not dissimilar to what Bruce went through with Jason, though that story had a happier ending. Over the years, Batman and Nightwing have always been on varying of goodwill toward one another, but this certainly helped Dick see his foster father in a different light, paving the way to their more explicitly loving modern-day relationship.

Ultimately, Dick Grayson would not give up on his role as a mentor. Not only did he help inspire heroes like Jon Kent's Superman, but he went on to influence and lead an entirely new generation of heroes. Currently, Nightwing is positioned to become DC’s next biggest hero by taking over from the Justice League, and his gentle and caring attitude toward the younger of the superhero community is at least partially due to his experience training and failing his own personal version of Red Hood.

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