[quote=@Lord Wraith]
Edit3:

Updated Timeline

~1981 - Bruce Wayne is born.

1990 - Barbara Gordon born.

1995 - Dick Grayson born

~1996 - Bruce begins training to be Batman

1999 - Jason Todd Born

2001 - Tim Drake born

2009 - Bruce first hits Gotham as Batman but is unknown by the general populace and only is a myth among criminals.

2010 - Batman has become an Urban Legend among Gotham, Dick Grayson's parents are killed and he is taken as a ward by Bruce Wayne.

2011 - First Appearance of Robin. Jason steals the tires off the Batmobile

2012 - Barbara Gordon graduates college becoming a member of the GCPD. The debut of Batgirl follows shortly afterwards. Jason discovers Bruce's identity. 

2013 - Batgirl is reluctantly accepted by Batman and Robin.

2014 - At the age of 19, Robin (Dick Grayson) retires from the Robin role feeling betrayed upon learning that Bruce had been training Jason Todd behind his back. Leaving the Batcave, Dick heads out into the world, leading to him doing some soul searching and travelling the world.

2015 - Batman begins to train Jason Todd? Barbara is attacked and crippled by the Joker. This tragedy brings Dick and Bruce closer together. 

2016 - Barbara becomes Oracle. Dick becomes Nightwing.


Batfamily Members:
Batman - Roughly Mid Thirties
Nightwing - 21
Oracle - 26
Jason Todd - 17
Tim Drake - 15
[/quote]

You did fuck the timeline up.

Bruce would've had to start training Jason in 2013 or 2014. :B