Green Arrow's 10 Greatest Failures
1. Had An Affair While Dating Black Canary - Straight Shooter
Oliver Queen has a lot in common with billionaire playboy Bruce Wayne, especially the "playboy" aspect. At times the Green Arrow was quite the scuzzball when it came to the fairer sex.
In the "Straight Shooter" storyline, Oliver teamed up with Jefferson Pierce, Black Lightning, to finance his niece Joanna on her path to becoming a lawyer.
Ollie and Joanna end up hooking up while they fought against an evil conglomerate in Star City. Almost immediately after the affair, the pair drift apart when Oliver reveals he's dating someone else. That someone else being Black Canary.
The world's greatest archer blames the entire affair on Joanna for some unknown reason, and even tells Black Canary not to come to the city since he feels so bad about the whole "cheating on her" thing.
Oliver's promiscuity continues even after this story and got so bad the writers had to change his sexuality to be polyamorous so that he could still have Black Canary and cheat on her without having any of that pesky guilt getting in his way.
This could easily be described as the Green Arrow's greatest failure. The worst part is that this wasn't because of some criminal plot or ultimate betrayal, this was just a fundamental failure of one man to stay truthful to the one woman in the multiverse who truly loved him, no matter what he did.