Well, I can hardly do Times Past stories without having The Shade in at least one, can I? ;)
In The Archer’s Quest, we find out that Oliver Queen made a bargain with The Shade in which he hired the immortal shadow-empowered semi-villain to take care of hiding/destroying various artifacts that would connect Oliver Queen to Green Arrow in the event of his death. Roy Harper asks why him instead of one of his loved ones? Ollie explains that being virtually immortal, Shade was more than likely to outlive any of Ollie’s loved ones and was emotionally detached enough to follow instructions on what Ollie would want destroyed.
This is sound reasoning. Unfortunately, this raises a troubling number of questions. How did Ollie find out that The Shade was more than a dangerous criminal who bothered The Flash? How did he find out The Shade was immortal? And why on earth would The Shade, mercenary as he is, feel inclined to play solicitor for Green Arrow regardless of how much he was being paid, given his long desire to remain neutral in dealing with superheroes when lives were not at stake?
The answer lies in Times Past. And not surprisingly, the answer involves a Spider. Alias The Spider, to be precise.
The Spider originally was a Golden Age archer hero, similar to Green Arrow. At least, that was what the public knew. The truth is that The Spider was a criminal mastermind who used his heroic identity to expose the crimes of his rivals while secretly taking over their turf with his own gangs.
The Shade took a hand in putting an end to his reign of terror in the 1950s, after The Spider grew bold enough to expand into Keystone City – partly because The Spider was part of a family of career criminals (The Ludlows) who had been trying to kill The Shade for the better part of a century and partly because The Spider had been planning to kill Keystone City’s resident retired superhero and Shade’s “enemy”, The Flash.
It later turned out that The Spider had an illegitimate son who decided to pick up where his dad left off and continued both family traditions – archery in the name of evil and trying to kill The Shade. And with the help of a few other villains, he came damn close to succeeding.
But before that – between the father and son – there was another Spider. A Spider who had no legacy to the Ludlows but had uncovered one of The Spider’s old hideaways, complete with the costume, the trick arrows and enough journals to reveal his secret criminal identity along with enough stashed loot to allow him to make a serious go as a super-villain.
Naturally, the report of a new villain called The Spider was enough to spark Shade’s interest. And the reports of an evil archer was enough to get Green Arrow’s attention. And so it was that a hero and a villain in name, if not in action (well, most of the time) did find common cause and form – if not a friendship – than an understanding of sorts as they dealt with their new mutual enemy.