Throughout the arc we see something that's been weighing heavily on Jason for awhile. His struggle with finding a path that is morally right and ensuring that justice is carried out. In Gotham the two don't always work hand in hand. Awhile ago he spoke to Alfred about dealing with Penguin and not feeling like he was actually making a difference. This happened just before he received Willis' letters.
Learning about his dad's love for him and how he tried to be there for him--apparently dying in prison because Penguin set him up--made Jason more determined. He figured out a new plan of attack that would work with the promise he made Bruce and be able to punish Oswald Copplepot when the law couldn't touch him. It still backfired on him as it also broke his relationship with Bruce. Since Bruce never tried to look into the matter and took what happened at face value he believes an attempt was made on Penguin's life.
Which feels like a nod of another time Bruce suspected foul play with Jason.
Jason never tries to tell Bruce what really happened on the rooftop, the diner or at Penguin's office. He probably resigned himself to the fact Bruce wouldn't believe him. It's a callback to the first arc of the Rebirth series where Jason argues with him over not being trusted like the others are. Now Bruce himself has already passed judgement on Jason and refuses to look into the matter. He said he regretted ever believing in Jason and over time more people stopped believing in him. Ducra who once had faith when Jason didn't have any in himself sent Essence to deal with him. Miguel thinks his actions are monstrous and leaves in disgust.
Throughout this volume of RHATO/RHO there have been a few father figures that have tried to guide Jason. Black Mask and Solitary offered him the chance to run their empires. Acting as an evil angel on his shoulder and seeing him as an heir. Bruce tries to force Jason to do what he wants with threats of imprisonment. When it doesn't look like he kept his end of their deal Bruce loses his temper and punishes him. Physically, emotionally, with exile and belittlement/insults.
When Willis Todd enters the picture it's after we heard about him being a bad father but saw him attempting to make amends with his letters. When we first see him as Wingman he visits a sheriff to get information on where Red Hood is heading. The first thing he says is a comment about how painful the injuries look. Was there pride in his voice because Jason kicked that man's ass? Besides telling the sheriff to write down everything Wingman shows a sense of humor similar to his sons'. There are clues about his identity pretty early on from his words (*1), his sense of style (*2) and when he hides his tattoo.
At the moment we don't know what Willis' connection to Solitary is. (*3) We do know Willis was supposed to be a test subject at the same prison. According to Solitary their minds were what was deemed important to the experiment not their bodies. Which, if true, means that if any other prisoner survived and had powers they would have mental abilities. As far as we know the real Willis doesn't have powers but Solitary might have gotten a lot of details wrong since he wasn't in his right mind anyway.
I'm not sure if Willis actually went to the prison since he made a point of mentioning in his letter that he was known for being wily. Maybe he even escaped before most of the prisoners were killed. He was able to track Jason's movements all the way to Hieve El Aqua. We noticeably never see Solitary in the same room as Willis (who was knocked out by Bunker for awhile) or get his insight on the prison it's self. Wingman attacks Jason and once you know for sure who he is it changes the context of the fight.
Unlike Solitary we don't have a scope of the amount of information Willis has on his son. Solitary spied on the Outlaws all the time to learn what he needed, we never get anything that hints that Willis has the same resources or powers. When Solitary shows up thinking he's Jason's father he instantly believes Jason will accept him. Willis on the other hand has no idea how Jason will react to him or if he's even willing to listen to a "stranger." That fear keeps him from revealing the truth, something he berates himself for. As is the train of thought in most ally vs ally fights he thinks attacking first then explaining himself is the best way to go.
Willis tries to encourage Jason by saying he's needed in Gotham (which Bunker interrupts) then attempts to push the issue again. I'm not sure why this is important to him as we don't get much insight into his thoughts. Is this just to have his son in a familiar setting to feel closer to him? Or was this Willis' attempt to make Jason build a life for himself? Maybe to settle things with Batman one way or another? We noticeably never get any scene where Willis or Bruce are in the same room nor see what his current opinion of Batman is.
He has no idea how to proceed and their meeting doesn't go like he thought it would. When Jason tells him that he can either be part of the solution or part of the problem Willis realizes that he can't force Jason to do what he wants. He can either be supportive of him or be pushed out of his life. That's something that none of the other father figures, including Bruce, seem to get. Jason can't be forced to walk the path others want him to take. The Prince of Gotham arc really puts into practice what Bruce said at the beginning of this volume about people surprising you if you give them a chance. But because Bruce is too concerned with his own preconceptions he misses out.
It's the first time Jason is really allowed to have full control of his life and make choices that will affect those around him. This is an important arc since he declares his independence when he undoes his legally dead status. While Jason has been mature and made tough choices in other stories this is him acting like an adult for the first time. Every other time we've seen him since he's become Red Hood he could do whatever he wanted with the safety net of not having a secret ID. Or even the idea that maybe someone in the bat family/his team could bail him out.
Unlike the pretend persona Jason had when he met Isabel he has to look after employees and act like a responsible person when he's not Red Hood. At first it seems easy enough but it gradually gets worse and he isn't able to hide how unhappy he is. It's something Essence quickly notices when they meet again. When Batman shows up he thinks Jason is acting stupid and insane as he can't understand what he's doing. As Wingman Willis sees Jason in situations where he's in complete control as Jason Todd and Red Hood. He also sees the negative side but still sticks with him despite not knowing what the outcome will be.
It's clear in the car ride that Willis is worried about Jason when he suggests that maybe Gotham isn't big enough for him. He's obviously regretting the fact he even asked his son to return to the city. Worse than that is Jason's reply when he asks how he can be so certain he can trust Wingman if he doesn't know who he is. Jasons' casual answer that he'll kill Wingman if he betrays him and Willis accepting those terms really drives home how uncomfortable it is for him. As a former henchman Willis probably heard similar threats from his bosses all the time and now he hears the same thing from his own son. It makes his relief that Jason did turn out better than him at the end have more of an impact. Since Willis allowed (didn't attempt to stop him) Jason to proceed how he saw fit he got to see what his true intentions were while Bruce still thinks the worst of Jason.
One thing that I heard a lot with the Willis story is that he's not a character that we can feel sorry about because of what we already heard about him in past stories. I don't think that's strictly true especially if this is a series about flawed people trying to earn redemption. It's not up to us to forgive him anyway and even if Jason wanted to work things out with his dad it's not going to happen over night. Bruce has also acted horribly to his family and this isn't even the first time. The audience is constantly expected to forget his actions with very little to no effort on Bruce's part. Even if DC decides to do the standard tale of Bruce screwing up with no consequences for him there are noticeable parallels between Willis and him.
Jason's dog appears right before he meets with Solitary and after he has his first encounter with Wingman. We've seen through flashbacks that when his parents fought Jason used to hide under the kitchen table with his dog, Sparky, for comfort. His new dog (called Dog) provides protection for him when she can by helping him stop Solitary and attacking Penguin. It's kind of notable that she stays by his side when his father figures are around. When it's against Wingman she only becomes relaxed after he stops attacking Jason.
Since Willis never fights him after they leave Hieve El Agua she doesn't need to fulfill the same role as Sparky. At least not with Willis, when Batman comes around Dog barks until Jason calls her over. He's not going to cower anymore and will look after her. It shows his growth from the scared kid was to the protector he's become.
Willis does come off more sympathetic than Bruce in this arc but both of them screwed up and did wrong by Jason. While Willis probably should have told his son the truth he still supported him as Wingman. Given everything else Jason was going through it's probably for the best that he didn't say anything yet. We still have the elephant in the room that needs to be eventually addressed in regards to how bad of a father Willis was and how Bruce is acting.
With Willis at least we've had acknowledgement that he was a bad father. With Bruce it's uncertain if DC will even let him own up to his mistakes, to let him be the one in the wrong that tries to make amends. Honestly I'm not to hopeful on Bruce taking responsiblity for his actions given the way DC has written him constantly treating his sons.
In the end Jason was right, he was his father's son. He did what Bruce would have wanted (not killing) and unintentionally made Willis proud.
*1 He refers to Jason as a prince which was his nickname for Jason when he was born. He also calls him son.
*2 Willis never explains why he used an old ID Jason previous had but it seems to be his way of connecting with his son. It also reminded me of a panel where Jason calls his dog...dog then comments about being bad at names. Likewise Willis, who previously considered becoming a supervillain when he was younger, also decided to take someone else's ID.
*3 This makes it hard to know where he gets his information since he knows that Jason was Wingman and is Red Hood. It's also curious because we don't know where he got the Wingman gear he has. Of course it also begs the question of where he was since he apparently didn't try to return to his son.
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