6. Beating & Killing Jason Todd (A Death In The Family)
This 1988 arc dealt with Jason Todd - the second Robin - searching for his birth mother. When he found her, he discovered that she was Sheila Haywood - an aid worker in Ethiopia - and the pair had an emotional reunion. However, unknown to Todd at the time, Batman's arch-enemy the Joker had discovered, prior to their reunion, that Sheila had previously performed "illegal operations on teenage girls" in Gotham City. After a procedure had gone wrong and had resulted in the death of a teenager, she was blacklisted as a medical professional. The Joker had used this information to blackmail Sheila into giving him the medical supplies that her agency had stockpiled in a nearby warehouse. Worse still, as well as selling those supplies on the black market and denying those in need of their usage, the Joker also replaced them with his laughing gas for kicks. When Robin turned up to help her in the warehouse, Joker brutally beat him with a crowbar. After Robin fell unconscious, Joker restrained him and his mother and left the pair in the warehouse with a time bomb. They tried desperately to escape, but weren't quick enough and Robin died when he threw himself on the bomb to shield his mother from the blast, but she was mortally wounded anyway. Batman then arrived too late to save them, which must have been incredibly painful for him.
