While Nightwing’s first attempt at being a big brother blew up in his face (literally) when Red Hood died, their early bond showed potential, if the nickname Dick Grayson gave to Jason Todd upon their first meeting is anything to go by. Although Jason has since been resurrected, the guilt surrounding his death has never left Dick, and it shows in how he handles his relationship with the current Robin, Damian Wayne.
The last two issues of the six-part Nightwing: Year One storyline published in 2005 and written by Chuck Dixon and Scott Beatty with art by Scott McDaniel, focus on Dick Grayson’s first interaction with Jason Todd. Dick Grayson has recently been fired as Robin when Batman believes he is prioritizing the Teen Titans and neglecting Gotham. Therefore, Dick and Bruce Wayne aren’t on good terms, to say the least. Dick flees Gotham for a while, but when he returns, he discovers that Batman has anointed someone else with the role of Robin: Jason Todd.
Dick quickly warms up to Jason on their first joint (albeit unplanned) mission, and he easily slips into the big brother role, complete with Jason’s own nickname. Of course, Dick is confused and upset once he sees another kid assuming the identity of Robin. However, his anger is directed at Bruce, not Jason. In fact, despite a somewhat rocky start, Dick apparently begins to enjoy showing Jason the ropes and explaining how Robin’s job should be done. He engages in easy banter, laughs at the story of how Jason became Robin, reminds him to never let a secret identity slip in public, and caps it off by giving Jason his very own nickname: “Little Wing.”
This nickname paints a bright future for the bond between Dick and Jason. As fellow Robins, they share a unique connection, and Dick is clearly eager to take Jason under his wing. Unfortunately, since he isn’t on speaking terms with Bruce Wayne at the time, Dick doesn’t spend much time with Jason during his short tenure as Robin. He avoids Gotham and regularly goes on off-world missions with the Teen Titans. This is the case when Jason is killed by the Joker. Upon his return to Earth, Dick immediately blames himself not only for missing Jason’s death, but also for rarely being present when he was alive. A relationship with Dick likely would have positively impacted Jason. If Dick had been available to mentor Jason and to reassure him that he doesn’t have to be a perfect Robin right away, perhaps Jason wouldn’t have focused so heavily on proving himself to Batman, and maybe he wouldn’t have died in the first place.
Despite Jason’s resurrection, Dick’s ongoing guilt has shaped how he views his relationship with Damian Wayne. When Darkseid apparently kills Bruce Wayne in Final Crisis, Dick becomes Batman and chooses Damian as his Robin for the same reason Bruce chose Jason: to teach him to channel his anger and use it for good. Recognizing the similarities between Jason and Damian, Dick is determined to not make the same mistake twice. He makes it his mission to be there for Damian in a way that he couldn’t be for Jason. He gives Damian positive reinforcement and shows him emotional vulnerability that directly contrasts with Damian’s upbringing within the League of Assassins and truly makes him both a better Robin and a better person. Even when Bruce returns to the present and Dick returns to being Nightwing, he shares a special bond with Damian Wayne that is oddly reminiscent of his initial, short-lived bond with Jason Todd.
Dick and Jason are still attempting to mend their relationship in November 2021’s Nightwing Annual 2021 #1, written by Tom Taylor with art by Cian Tormey and Daniel HDR. The pair reaffirm their status as brothers, but it is clear that their bond could have been much stronger if Dick was there for Jason from the beginning. Every appearance of Dick and Damian’s relationship will continue to leave fans wondering what could have been for Nightwing and Red Hood; or, as Dick dubbed him, “Little Wing.”