Post-Crisis
In this time frame Willis was usually just mentioned and rarely seen. (*1) He appeared in few panels working for Two Face but other than a family portrait with little Jason and Catherine he never turned up in an image with his son. We don't really know much about him or his relationship with his family at this point. Many fans assumed he was at least a loving father simply because Jason was upset about his death. We know he was away from home a lot usually working or in jail.
Collins wrote the story that dealt with Jason attacking Two Face after finding out his dad died which Collins has stated was never finished. (*2) Interesting detail about the story that's never really talked about is the fact Willis is listed as presumed dead. Bruce and Jason believe he is but they never have any proof. Later on during DITF this was forgotten like other Jason plots. Catherine was said to have died from an illness instead of an O.D. and Willis was shown in a panel apparently gunned down by Two Face.
It's iffy if anything Sheila Haywood said was true. Since she was something of con woman it's unknown if she was even Jason's birth mother. She seemed to claim she went to school after Jason was born and left for good when Willis fell for Catherine while she was gone. With Joker it's revealed Shelia fled Gotham after a girl died from the implied illegal abortions she performed. Was she lying? Well she did recognize Bruce Wayne so it's possible that she wanted to get something from him and pretending she was the mother was the easiest way.
I think we were supposed to assume Willis was a ladies man since he had a black book with women's names in it. I guess. We never find out how he knew these women (one who was a spy and another who was Lady Shiva) or if he was in romantic relationships with them. It seems far-fetched regardless.
New 52/DCYOU
The first time we get to actually see Willis for a good amount of time is in Red Hood and the Outlaws #0 VOL. 1. There was some negativity around this period for what an ass Willis is in the issue since Jason seemed genuinely upset in the Post-Crisis version's death. I'm willing to be more flexible with this because we never had much information on him. I'll admit the issue wasn't one of my favorites and I believe that's partly because Willis was rather lackluster. I could deal with him being different but at the same time I wanted him to be more than what we got.
Willis was a womanizing (apparently amoral) criminal that Jason had no apparent affection for. Told in Jason's POV we are shown how Willis and Catherine (not the stepmother in this canon) got together in their teens. I like this scenario as it explains a lot and puts Bruce closer to their ages. Catherine fights with Willis and no one apparently liked him. He brags to his son about fleeing the scene of a hit and run much to Jason's disgust. Willis acts immature, sex crazed (even while Catherine is giving birth he cheats on her though I don't know how Anyone knows that), stupid and doesn't seem to have any redeeming qualities.
It's shown that Willis' is actually one of the youngest of seven kids and hinted that he came from a broken home where his dad was an abuser. There's been mentions of him being abusive too as Jason tells Duella Dent that his dad beat his mom up for wasting money on cigarettes. In RHATO #18 VOL. 1 Jason mentions fearing his father would make good on his drunken ranting to get rid of his "two mistakes." This led to poor sleeping conditions as he also worried about Catherine dying and says it was hard to rest on bruises. Willis is said to be a drug dealer in Secret Origins.
Jason seemed to hate his father when he watches a bullet being taken out of Willis' back and wishes it killed him. Though Jason claims he's fighting to save his "dad" when Joker said he had him.
It's shown that Willis' is actually one of the youngest of seven kids and hinted that he came from a broken home where his dad was an abuser. There's been mentions of him being abusive too as Jason tells Duella Dent that his dad beat his mom up for wasting money on cigarettes. In RHATO #18 VOL. 1 Jason mentions fearing his father would make good on his drunken ranting to get rid of his "two mistakes." This led to poor sleeping conditions as he also worried about Catherine dying and says it was hard to rest on bruises. Willis is said to be a drug dealer in Secret Origins.
Jason seemed to hate his father when he watches a bullet being taken out of Willis' back and wishes it killed him. Though Jason claims he's fighting to save his "dad" when Joker said he had him.
The only time we see anything close to fatherly love is Willis showing Jason the ropes of his job and being proud of his son. Jason himself is shown taking care of both of his parents, Catherine when she's high and Willis when he was drunk. Willis brags about getting a bat shaped mark after an encounter with Batman which doesn't impress his son. Jason says his dad was arrested and died in prison not seeming to be bothered by this fact. We don't know what he did to earn life in prison although Willis seems curiously sad in the panel he's being taken away in a police car.
*1 Willis doesn't look like Jason in the pictures Gordon shows Batman but he does later on. In fact Wilis looks like an older version of Jason. Later on in New 52 he doesn't look that much like his son.
*2 To quote from the interview:
You didn't create Jason Todd, but I'm curious how much of the character's development was you and how much freedom you had?
I'm afraid I don't remember. I just know that I was asked to do a reboot. Starting over was definitely not my idea. I may have come up with the Jason Todd as juvie notion. It seemed that if Batman was going to essentially fire Dick Grayson because he didn't want to put Robin in harm's way anymore, then the only way he'd take a new Robin on was if the kid might die or otherwise go down a criminal path if he didn't.
I had a whole storyline developed that was later ignored that had to do with Jason's father and Two-Face. I frankly don't remember exactly where I was headed, just that the book dropped my concept and went in a direction that ultimately led to the fans voting Jason's death.
*3 Jason mentions a birth mother suggesting Catherine wasn't his biological mother.
Rebirth
I have a couple theories on Willis but with the possible exception of Catherine not being the birth mom (*3) it seems like everything from New 52/DCYOU still happened. The big shock happened in a panel from the RHATO Annual #1 Vol. 2. Jason remembers when his dad stole a couple of tickets for the circus from an elderly couple. Little Jason watches the Graysons in awe as Willis looks at Jason's reaction. It's literally the most touching panel of the two. Willis shows a softer side which means he honestly does have some affection for his son.*1 Willis doesn't look like Jason in the pictures Gordon shows Batman but he does later on. In fact Wilis looks like an older version of Jason. Later on in New 52 he doesn't look that much like his son.
*2 To quote from the interview:
You didn't create Jason Todd, but I'm curious how much of the character's development was you and how much freedom you had?
I'm afraid I don't remember. I just know that I was asked to do a reboot. Starting over was definitely not my idea. I may have come up with the Jason Todd as juvie notion. It seemed that if Batman was going to essentially fire Dick Grayson because he didn't want to put Robin in harm's way anymore, then the only way he'd take a new Robin on was if the kid might die or otherwise go down a criminal path if he didn't.
I had a whole storyline developed that was later ignored that had to do with Jason's father and Two-Face. I frankly don't remember exactly where I was headed, just that the book dropped my concept and went in a direction that ultimately led to the fans voting Jason's death.
*3 Jason mentions a birth mother suggesting Catherine wasn't his biological mother.
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