The best chance in my opinion was after The New Batman Adventures (extension of B:TAS) ended. Nightwing's character hadn't been fully explored yet, i.e. he hadn't reconciled with Bruce or Babs yet. He's talked to Tim like once (Old Wounds). There was a lot of potential there, but then... we got Batman Beyond instead.
I've heard rumors that Bruce Timm considered making a Nightwing spinoff but he didn't like Dick Grayson that much as a character, and instead went with creating Batman: Beyond. Who knows though, just a rumor, maybe the execs just flat out told him that Nightwing wouldn't have enough brand name to hold a TV show on its own. Batman: Beyond still has Batman in the title, if they had a Nightwing show they might have to make it like... "Nightwing: Batman's Protege", or "Batman Adventures presents: Nightwing", or "Nightwing: Robin No More", something stupid and corny like that instead of a simple "Nightwing: The Animated Series".
I don't see much spin-off potential from Young Justice, at least not yet. So far the YJ Nightwing has been a pretty flat character, much more flat than the YJ season 1 Robin.
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