All parents make mistakes
(Also don't judge timelines. They are often not correct in the comics. So I slightly altered it to be my own! Please enjoy)
Bruce isn't perfect, and he's never been perfect.
His first thought when he took Dick in was that "having children is easy. You tell them what to do and they do it". Because when you have a british retired war veteran as a guardian you kind of end up thinking that all kids respect everyone.
That wasn't the case, the first couple of nights that Dick was staying in the manor he would do "bad" things, just to test the waters. Throw fancy china, track mud into the house, give Ace WAAYY too many treats. He also ran multiple times and sometimes for multiple days, to places that Alfred couldn't even track. Some things were more subtle than others. But one stuck out the most.
Dick's first charity gala. He was in a cute little suit with a very nice blue bowtie, a matching vest underneath, his hair combed back with one little cowlick sticking out in the front.
"Alright Dick, I want you on your best behavior." Bruce says, "I've been going to these kinds of events since I was your age." Dick, scheming, just nods and tries to find some old guy he can mess with.
The night is going well until the sounds of glasses crashing and one lady shouting peaks to Bruce's ears. He rushes towards the sound, his stomach twists of anxiety.
Dick was standing there, arms folded. One of the most prestigious CEOs was on the ground, expensive crimson wine covers her once champagne coloured dress. A waiter is trying to dab off as much as he can while she shouts at Dick, who stands there blankly.
"What happened?!" Bruce says, "This ward of yours Mr. Wayne! He is just a nightmare!" She stands up, pushing the waiter aside. "Firstly he insults my husband! Calling him decrepit! Secondly he does this! 5 entire glasses of wine all over my dress! Do you know how much this costed me?!" Bruce chokes back the anxiety of talking to someone that his, now son, has disrupt.
"I'm so sorry for his behavior ma'am! I-I'll pay for the damages done to your dress! Better yet! I have an entirely new one made!" He says nervously, attempting to kiss her hand as a peace gesture but she throws it away from him. "You'd know better than to let ruffians into the upper class life, Mr. Wayne."
Bruce's first mistake, thinking kids are easy. And taking problem children to very expensive galas is a very difficult thing to do.
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Jason comes around. Bruce catches him stealing the wheels off the Batmobile. Obviously this doesn't make a GREAT first impression but he ignores it.
A brand new start after his prized ward Dick Grayson decided that he was done with living in the shadow of Bruce Wayne.
Jason was already a better behaved kid compared to Dick. But he still had his down sides... When Bruce had let him take on the Robin mantle he didn't expect that Jason would be SO invested in it.
It became a really big problem, that all Jason wanted to do was solve mysteries and fight crime. And it got to the point that Bruce had to ground him from patrol multiple times because his grades and behavior in class were slipping.
Obviously one thing leads to another and Bruce find himself at a gravesite with tears streaming down his face. All these thoughts ran through his head. "Maybe if I had helped him find his mom." "Maybe if I hadn't said no." "Maybe if I tracked him better?" "Maybe if I never made him Robin."
Bruce's second mistake, thinking this kid was easier. Thinking that there could have been any timeline where he stopped it.
Batman's greatest mistake.
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Bruce hadn't done a lot with Tim. And that's actually his mistake, not doing enough.
Tim was and always will be a reserved kid. He was quiet but smart. And while you wouldn't expect it, he was snobby but could also stick up for someone who needed it.
So when a 17 year old knocks on your door and says he knows your secret identity and that Blüdhaven's one and only Nightwing had chosen HIM to be the next Robin, you don't get too excited. After all, your son is dead.
So yes, while Tim becomes one of, if not the best, detective there ever will be. He doesn't become the greatest Robin. And that is because, Robin is the son. And while Tim, now, is treated as the 3rd son, he wasn't for quite sometime.
Bruce's third mistake, not treating Tim as a son before it was too late.
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So, to be fair, Bruce had adopted Cass 3 years after he adopted Dick. But she stayed out of EVERYTHING. Which sometimes made Bruce forget that she was there.
12 year old Dick Grayson was in the study, doing backflips off the chandeliers and a voiceless 5 year old Cassandra Cain sits there, at a small coffee table, attempting to colour in the lines after her hands got so molded to the grip of a sword.
Her hands shake with every stroke, with every bump that Dick does into the table. A tear rolls off of her round cheeks as she tries to communicate silently to her reckless older brother that he is causing her to ruin her drawing.
Later on, after Alfred scolds Dick to get down and to start his homework, he sits down with Cassandra. His calm, peaceful eyes look at her with kindness.
"Now Miss Cassandra, I do believe that it is part of my duty to help your communication skills grow." She blinks at him, the wise words sound slow and chewed up to her. Alfred realizes and rewords his sentence in a simpler tone.
This wasn't Bruce's mistake. In fact, he hadn't really made any mistakes with Cass. But it took her longer than they had anticipated to teach her how to properly communicate.
Cass would get upset, or overwhelmed, or tired and just start an entire duel with someone. One time, Dick was being especially difficult. He was just arguing with Bruce and Alfred about something stupid, and just wouldn't quit. Cass already had a bad day, she was tired and it felt like her feet were attached to chains.
"I don't get it. Cassandra gets whatever she wants! You treat her like she's some.. Frilly princess!" Dick says, they're fighting in the kitchen, Bruce just stares at him with his arms folded. Cass drags her feet, eyes locked onto Dick.
"Dick, you have to understand that you are grounded for good reason! You are not old enough to drive, what makes you think that you could drive the Batmobile?!" Bruce says before noticing Cass. "Hey! I didn't realize you came in! Are you hungry?" She ignores him, looking at Dick, who was thankfully standing close enough to a wall. She makes a quick move. A batarang gets lodged into the wall behind him, a long thin cut appears along his cheek.
Bruce, Dick, and Alfred stand there, shocked and in silence. Cass looks at Bruce and Alfred with eyes that show the slightest bit of pride. "Dinner would be nice" She says before leaving the kitchen. "IS SHE GROUNDED NOW?" Dick says, Bruce blinks and stammers. "I-Uh- Cass! You're grounded!"
Bruce's fourth mistake, keeping the batarangs in reach of children.
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I was going to write about Damian and Stephanie, but this post is already so long so I decided against it.
