Tim Drake first went to the Iceberg Lounge when he was seven years old.
Due to a rather unfortunate car collision his nanny, a sweet woman named Lillian, had never arrived to care for him while his parents went for dinner with their biggest sponsor. the woman lived thankfully, but when Tim realised he was home alone he grew fearful and took it upon himself to go and find his parents.
Luckily he was paranoid enough with them leaving so frequently he had… found a way to permanently track them.
Tim had only been allowed into the seedy lounge due to the fact that the bouncer on duty recognised him and knew his parents were inside.
Escorting the young boy inside after Tim very politely explained the situation, the man left him in the staff rom for the security and went to get the elder Drakes.
Who promptly betrayed Tim for so recklessly leaving the very safe mansion in Bristol on a public bus and then walking through Gotham in his pyjamas into a very respectful restaurant owned by a very important man all because his nanny was a little late-
Until an incredibly well dressed man came in, waving a cane around with a gleeful look on his face, “Jack! Janet! You didn’t tell me your little one was coming!”
Oswald Cobblepot, AKA the Penguin, didn’t seem to care for the frazzled and furious looks that quickly vanished into something appeasing from the Drakes and instead approached the wide eyed boy who just realised where exactly he was.
Tim looked up at the man and, knowing full well he was one of the most powerful mobsters in the whole world, promptly panicked and went into full faun mode, “I-I’m sorry Mister Pen- Mister Cobblepot, I was just alone and I got scared and I- I wanted my parents-“
Cobblepot, a feared man who had made his very name and appearance enough for people to run or give appeasing bow in a hopes he wouldn’t have them shot on the spot, then cooed.
Tim was then given a new set of pyjamas bought by a henchmen and was given his own room to sleep in for the night while his parents finished their dinner. Tim was given a hot chocolate with penguins shaped marshmallows and despite being in such a dangerous place, he felt so very safe.
Cobblepot tucked Tim in himself and with a somewhat dark look in his eyes said to him, “Look, kiddo, there’s… some people in this world who say they are good or that they will do good by and they don’t. These folks they, ah, don’t always seem like the type and that ain’t your fault, ya hear?”
Tim had listened with a confused expression but chose to keep the words in mind after considering how the older man had built his inheritance up to something so grand. He had to be smart, had to have good advice, even if he used said knowledge for nefarious means.
Tim had left a few hours later, half asleep in his mothers arms, with Cobblepot’s last words in his mind,
“If you ever need anything, you just come by, okay? Don’t worry, I won’t let anything bad happen ‘round ya, not anything that could make the big bat cross with you. But… if you need helps, any at all, just say the word.”
Tim didn’t exactly go and see the monster after that, not at least straight away, but when he got a sprained ankle one night after taking photos of Batman and Robin he panicked. Seen as The Iceberg Lounge was closer than the bus stop and he was really in a lot of pain, the then eight year old decided that it was better to get help quickly than have to wait for hours and only help himself.
So, Tim went to the Lounge and calmly asked the security if they could ask Mister Cobblepot if he could please come help him.
Having been told to allow the boy in if he came by, the man was already radioing to alert the boss only to widen his eyes at the very obviously swollen ankle the boy was standing on.
Picking Tim up carefully and taking him into the office room, he quickly got some ice and wrapped it around the limb.
Cobblepot had rushed in, alarmed at hearing the boy had been hurt and not having any other context, just to find himself telling the boy to be more careful when climbing around to take photos.
Tim, who had been given prescription medicine that Cobblepot had promised him was safe and the young boy had somewhat recklessly decided to trust, was then sleepy and embarrassed and accidentally confessed to taking photos of Batman.
Cobblepot had just been about to order his men to contact his parents, who were in Peru and unavailable, and was left with curiosity.
Tim showed him the actually very good photos and Cobblepot was left with a choice.
Use the boy for information on how he was finding and tracking the Bat or… leave the golden chance to get one over the Big Bat in favour of not hurting the young boy.
If he had lived even the slightest bit crueler of a life, if he had taken the marketing and business opportunity of dealing in kiddies and drugs and the things that are truely evil and not just money control, maybe he would have used the kid.
But this Cobblepot wasn’t as bitter as he could have been, all due to one interaction with Martha Wayne where the woman had chosen him to talk to in a crowd or ‘normal’ people.
He had to repay that kindness in more than just procreating her son.
So, Cobblepot bought Tim some new shoes and a new camera lense and told him come by in a few days so he could check his ankle was healing and maybe to see some more photos?
Tim then started to send printed out photos to Cobblepot every few weeks. Never really of Batman, but of everything and anything he photographed.
Cobblepot adored them and framed his favourite.
When winter came and Tim took as many photos as he could of the snowed in Gotham, the ice rinks and the penguins sat the zoo, Cobblepot had many of them framed and soon half of The Iceberg Lounge was covered in them.
When Robin died Tim went to Cobblepot and sobbed.
The man hadn’t understood why he was so upset at first even though he was a bit shaken by the boy dying, but all that mattered was the kid chose to come to him even though his parents were in town.
That night they talked a lot.
Tim confessed that he wanted to be like Robin, maybe not a hero, but brave and loud and funny and bright and not all polite wording, formal clothes and scheming for partnerships. He wanted to be someone more than a company and a last name, even if he did like his life and all of his friends.
Oswald opened up about his disability and how much he hated it. He told Tim about when Martha Wayne spoke to him like a person, greeting him without bending down or making a show of looking lower. He talked about how he wishes he was different and that he is only so cruel so people respect him.
They make a promise to each other that night.
Oswald promises to be nicer to himself so Tim won’t be worried about him, as well as a more loose promise of trying to avoid the meaner methods of his business.
Tim promises to be whoever he wants and that if her ever becomes Robin, he’ll turn a blind eye to the Lounge.
Tim does become Robin a year later, debuting two years later after his extensive training in an improved suit and with a far a more calculating and measured approach to the role than the last two.
Oswald didn’t stop dealing in weapons and some of the lesser drugs, but he did stop with the drugs that were harder to control and kept getting out of his connections. He still killed those who wronged him, but he gave one chance for improvement and instead of killing his men who failed he dropped their rank to things like janitors or waiters.
Oswald is hurt when his favourite gothamite stops coming around every few months for a chat or sending photos. He worries he upset the boy he started seeing as a family member, which makes him focus on the family aspects of his business, how it started and what he turned it into.
It’s almost a whole year later, a whole year of hearing about and seeing the new Robin get hurt on TV, that he meets the boy wonder.
Tim looks at Oswald, Batman commanding in his earpiece, in full gear and stares at the man in his full Penguin gear.
They lock eyes and Oswald just knows.
Twenty men have guns pointed at him, ready to fire when their boss says so, only to lower them when he stamps his cane down.
Awkwardly they all leave the room, knowing the boss is telling them too but consisted as to why.
Tim starts crying, feeling like he did when his parents were yelling at him when he first entered the Iceberg Lounge, and clenches his fist at his side and tries not to beg forgiveness.
Oswald, hurt that Robin is Tim and that Tim lied, is just so relieved because this means Tim wasn’t angry at him he just couldn’t be friends with a mod boss and be Robin at the same time.
The man smiles, wide and showing off his two golden teeth, he laughs heartily and shouts, “Congratulations, my boy! I can think of no one better for the role!”
Robin runs into Penguins arms, begging for forgiveness and asking for them to please not fight!
Oswald holds the boy for a moment before pulling away, “Listen, the boy behind this mask will always have a safe space in my Lounge, but the mask himself has a job to do. Leave me and the Bat to tussle, for both our sake.”
Sniffling, Tim pulls away and asks in a hopeful but resigned voice, “Can’t you just… stop?”
Oswald smiles and pulls the boy down for a quick squeeze, “You’ve already changed me a lot, but business don’t care for softies. Now, get outa here! My boys are tired so we’re… we’re gonna turn in for the night.”
Tim smiles, knowing full well that Oswald is giving into his puppy eyes but not willing to push it.
Batman, who was listening the whole time, is fucking furious, but can’t deny that Penguin has shaped up in the last few years and isn’t as much of a threat.
Robin is benched for three months and in that time trains with Barbara.
Tim visits Oswald, now named Uncle Ossie, every few months and sends him all of his photos even the odd ones from patrol.
Red Robin works with Penguin often, trading information and getting supplies for The Nest when he is too angry or petty to talk to anyone in the Cave.
Tim Drake has free access to the Lounge and often brings his friends. He knows all the workers names and has his own room next to his Uncle’s, who will always find the time to greet his boy with a big hug and a kiss on the cheek that he has managed to master with his pointed nose.
Everyone thinks Tim is apart of the mob, but considering he’s a CEO of Drake Industries and CFO and COO of Wayne Enterprises and seems to be a bit ignorant to crime statistics, they assume he’s just another rich dumbass or knows what he’s getting himself into.
Red Robin always shows up to the places encroaching on Penguins turf.
Tim Drake spends 57,000$ dollars on a cane made from a meteor that landed in the Arctic and has penguins engraved in the handle.
Red Robin yells at Red Hood for being mean to his ‘uncle’ and everyone assumes that’s why Penguin has gone soft, but when that same Red Robin single handedly beats the hell out of a mind controlled Superboy they decided it’s warranted.
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