Archive of Our Own ^beta

Chapter Text

Gotham city isn’t known for being the calm and restful center of the universe. Even so, Tim had already spent most of his day fielding calls from upset customers thanks to a televised fight between Robin and a mutant, winged squirrel that was wreaking havoc over the streets of Robbinsville, leaving quite a few customers without water or power or both. Insurance claims had been rolling in all morning, and it was taking everything Tim had not to rip his work phone from the wall but instead direct their calls to the Wayne Foundation hotline set up for exactly this reason. When he finally did get a moment to breathe, it was only to get a notification on his phone that there had been two sightings of the Riddler wandering around the Diamond District. The police were almost positive it was an early Halloween costume, which was doing nothing to calm the masses already on edge from a flying squirrel the size of a pick-up truck.

Reading through the news reports that evening while waiting for his shift to run out, Tim knew there were worse jobs in Gotham than insurance agent. Hearing his work email notification going off yet again, he’s hard pressed to think of another at the moment. As he shoots off an email to a client about looking into their claim asap, he hears the glass door to the small insurance office open and watches Stephanie Brown,the goddamn Batgirl, walk into the agency and catch his eye. He puts masked vigilante at the top of the list.

--

“Are you sure you don't want to upgrade to the Pick 4 plan? While the area around Gotham University is relatively safe, I always recommend anyone living within a 5 mile radius of Robinson Park to include Poison Ivy on their home and auto. And with her recently comes the necessary coverage for Harley,” Tim says, doing his best to run through the categories of coverage for Batgirl without losing his cool. He's trying not to watch the clock tick closer and closer to seven, sun already setting, deeply confused as to why she's shopping for insurance policies.

“Doesn't the Harley coverage cover the Joker as well? I thought that was a special bundle,” Stephanie says, perusing the paperwork he had handed her that covers the breakdown of their additional Gotham options.

“Not for the last few years. After that big public blow up between them,” quite literally, Tim muses to himself. “When she said she wasn't working with him anymore, we had to discontinue that program.”

“Good for her,” Stephanie mumbles, not looking up as Tim tries to cover his smirk.

“I'm hoping they'll reinstate it for her and Ivy, but until then, if you want the best coverage, the Pick 4 is really the best I can offer you.”

“The Joker's been in Arkham for the last couple years though, why offer him? Think he's getting out soon or something?” Stephanie looks up at him, her blue gaze critical.

Tim doesn't mean to, but scoffs at her slightly, “When has being locked up ever stopped him from getting out? Every few years he tries to make a break for it, and every few years there's collateral damage, and you're not quite far enough away from Arkham for it to be safe.”

“And where would that be?” Stephanie asks, tone sharp enough to surprise Tim for a moment, be he regains his cool.

“Off-world,” Tim replies dryly, earning a snort from the blonde.

“Personally I think he should be automatically added to any policy, especially for anyone near Gotham, but until those changes go through, or he dies, I still suggest him on every policy. Ivy, and with her Harley. The only question is, with Halloween so close, if you want to include Scarecrow or Riddler? The Riddler is best if your health insurance already covers any form of long term medical leave already, but if not, I suggest Scarecrow and adding our short term disability, so you won't lose any money if you have to recover from any fear toxin.”

“Jesus,” Stephanie says as Tim hands over another pamphlet explaining the differences between long and short term disability. “I can see why you get such good reviews.”

Tim smiles at the off-handed compliment, “I take this pretty seriously.”

While she reads over the pamphlets again, he gives her a critical once-over. She’s in civilian clothing, purple top just visible under a blue hoodie, long blonde hair pulled back in a messy bun, the epitome of exhausted college student chic. Her pointed question and attitude about Tim’s well informed opinion of insurance policies keeps confusing him.
He's still trying to figure out why Batgirl of all people would be so far out of her normal hunting grounds, especially when Tim's pretty sure that everything she has is owned or being paid for by Wayne Enterprise. While he's unsure of what she's doing here, he's always found the best course of action when dealing with any new situation to wait and let the other person talk themselves into a corner. Coming at a situation head-on had never been the Drake way. Subterfuge, duplicity, and good old-fashioned misdirection were the best lessons he learned from his mother. When none of these seem to apply quite yet, he sits quietly watching her look over the pamphlets, mouth twisting in confusion as she continues reading.

“I'm here to answer any questions,” Tim offers, as she sighs deeply.

“Just trying to figure out what the overall premium is for all this. And if all of this is necessary.”

“Let me break it down,” Tim plays along, waking his computer up and inputting her information. “Do you own, rent, or are you in a dorm?”

“Rent,” she says slowly, aware he knew the answer from the beginning of their long conversation.

“Is your car paid off, loan, or lease?” Tim asks, trying to keep his eyes on the screen and not on Stephanie watching him with interest.

“Loan.”

“Great. Do you have a tendency to drive in neighborhoods more like Burnley or the Upper West Side?”

“West Side,” she answers, trying to look at his computer screen.

“Alright. Do you work or are you living off loans and grants?”

“Loans. Some grants,” Stephanie mumbles, a light flush coming to her cheeks. Tim assumes the 'grants' were a nice way of saying Bruce Wayne was paying whatever her loans didn't cover, which included her very nice apartment location.

“Do you have private insurance or are you covered through the university?”

“Private.”

“Then this is the best plan for you,” Tim says, turning the screen so she could see it. “The Pick 4 with Ivy, Harley, Joker, and your choice between the Two-Face gang since you spend more time in his possible hit area or Scarecrow due to the season," Tim says, choosing a rogue for her. "Once Halloween is over, I would suggest going online or calling to get your policy changed to include Penguin, since he gets more active the colder it gets. If you’re on your parents insurance, and don't work, don't worry about short or long term insurance just yet. Let them foot the bill for a little longer. Bundle renters and auto, pay every six months, and you'll get a massive discount,” Tim hits print while he walks Batgirl through all the steps in her plan, pointing out at the bottom of the screen the discount she would receive once she signed her name.

He gets up to grab the paperwork from the shared printer, noticing Stephanie trying to look around his desk while he walks away, but the printer is too close for her find whatever she was hoping to see. Tim pretends for both their sakes he didn’t notice.

“Plus, you have a clean auto record as far as we can see, and you can get a new member discount. Keep your record clean, and you can get a cash back bonus at the beginning of each renewal year,” he continues, stapling both the packet for his records and her personal one.

“Now, let's get you signed up,” Tim concludes, smiling and holding a pen out for Stephanie, who's staring at him in surprise.
Tim still worries slightly why Batgirl would need such extensive coverage, but a commission was a commission.

--

Tim walks quickly from his car to his four story walk-up in Newtown, not the safest neighborhood to be out late in, but by far not the worst in Gotham.After Stephanie had finally left, asking to think it all over instead of signing up, Tim had finished up a hurried conversation with another client about adding a new car. It was later than Tim normally returned to his neighborhood, but with his favorite Thai place still open, it gives him one more day to put off grocery shopping.
Showering quickly and changing into sweats, Tim hunkers down at his well loved desk, and pulls up the GCPD breaking news feed on his laptop, letting his desktop run a program to pull rouge names and locations from the news articles from the day. While the mostly redacted feed wasn’t the most reliable source for information, it was always a good start.
He adds a few notes to his ever growing Excel sheet before turning to the real goldmine: Gotham tweets. No one ever stayed quiet when it involved meeting their favorite bat or coming across another crime GCPD wasn't aware of yet.

Tim hadn't been lying to Batgirl when he told her he took his job seriously. The crime fighting world of Gotham had always been a hobby of his, from the moment he realized Robin was Dick Grayson, and continued to make the connections to Jason Todd, Stephanie Brown, and Damian Wayne. When he was a child, his interest had been much more involved, up to following the bats whenever he could, almost getting caught a time or two. He was caught once by Catwoman, who had also been spying on Batman, and she had told him if she caught him snooping around again, she was going to take him home and make him one of her kittens.

Not a week later, both his parents were killed in a hostage situation gone wrong.

With no other living family and no close associates, Tim had been placed into foster care. There had been talk of different business partners adopting him or maybe Bruce Wayne. A couple months later though, Jason Todd was dead, and Bruce was in no shape to take on another child. Tim’s parent's business associates had been more worried about trying not to run Drake Industries into the ground than about an eleven year old orphan.

So Tim had given up his camera, his pictures, and his sneaking out to watch crime fighters to sneaking out at night to get away from the overcrowded homes he was continually moved to and from. Most families had started out wanting him until it came to light that his trust fund had been embezzled long before his parents' deaths and all Tim would be inheriting was his last name. After that, Tim became another young child Gotham was waiting to age out.
Instead, he worked as hard as possible to get his GED and used the grants WE had set up for misbegotten youth to get his AA in business before he aged out completely and lost what little state money he could get to pay for the degree.

When a classmate in an intro insurance class had mentioned his father was always looking for more insurance agents and there was always something getting destroyed by someone, Tim got his degree, put in some applications, and called it a day. He honestly hadn't expected to get quite a few job offers plus signing bonuses. Tim, figuring it was a great way to kick start his resume, took the one with the best options. He passed the state exam easily, and got a book of business cards with his name stamped on them and good luck from his new boss.
Tim had not realized that his old hobby would end up being such a boon to his new career. Apparently, no one else enjoyed running a statistical analysis on the cities crime rates with a crossover for geography and residential status. He had started mapping the city when he was younger to make it easier to keep track of patrol routes for Batman and Robin, so all it had taken was a few tweaks here and there to change it from watching the vigilantes to watching the rogues. His commissions had skyrocketed once his clients had started spreading his name around as some kind of evil-doer guru. He had started a small quarterly newsletter for them so that everyone could be kept up to date on new policies and activity on the streets.
When Catwoman had decided to weave back and forth from neutral party to burglar, Tim had made sure to let his few clients closer to the Diamond District to up their insurance maximums. When Black Mask had apparently come back from the dead, he had sent an alert to all his East End clients and hoped for the best. Red Hood had taken care of that problem before it could really take off though, which really helped keep premiums down.

As he read through all the #Gotham tweets and blog posts he could handle, he added the most pertinent information to his program and let it run while he washed up his few cups and prepped his coffee pot for the next morning. As he was heading to bed, he got a police alert on his phone that both the Red Hood and Batgirl had been spotted in Otisburg. Tim sighed deeply, and tried not to think about all the claims he was going to have to put in tomorrow morning.

--

“Mr. Ramirez, you did not include Killer Croc in your Pick 3. Yes, sir. Yes, sir, I'm looking at your most recent policy change right now. You removed him over six months ago when you downgraded from your Pick 4. If the police are able to prove he was working with one of your covered rogues, there is a minimum payout available to you. Yes, sir. Yes, sir, you're welcome. You can review all this information online as well. You too, sir,” Tim caught the sigh that wanted to escape, noticing Stephanie was standing patiently at his desk while he finished his call.

“It was Ms. Brown, right?” Tim asks, getting up to shake her hand, pretending for her benefit. It wouldn't do to make it sound as if he remembered every detail about her last visit to his desk.

“Good memory! But call me Stephanie,” she says brightly, a surprised smile on her face.

“I have to say, I'm shocked to see you back. After a few days, most people have moved on to different agencies. Are you ready to sign up for your renters insurance?”

“I think so, but I've got a few more questions?” her lips twist, a shy look on her face as Tim pulls a chair out from in front of his desk and waves for her to sit.

“It's what I'm here for,” Tim says, putting on his best Drake Industries smile. He had gone through the policy information almost three times with her on her last visit. It was already after six, and he was not looking forward to having another late night, especially while he was dealing with the claims from the giant squirrel attack.

“It's less about renters, and more about how you seem to know who's going to hit where? I've checked with a couple other places, and no one else just seemed to know who to choose. A couple friends bought from you, and they say you're great at what you do, but I'm worried about making the wrong choice. You guys aren't exactly cheap, you know?” Stephanie’s sarcastic tilt puts Tim’s nerves on edge, even though her face shows nothing but interest.

Tim wants to snap that it shouldn't matter how much it was, she was being bankrolled by Batman of all people.

“Who recommended me to you?” he asks instead, the desire to know who he could have as a client that could also know Stephanie overtaking his annoyance. Most of his clientele was located in uptown, and even as Batgirl, Stephanie Brown had a tendency to stick to the downtown area.

“Does it matter?” Stephanie asks, giving him a suspicious look.

“It does to me. Your friends should have been able to tell you that I get my information from the police releases, just like everyone else. Plus, I like to send my appreciation to my clients,” Tim said, watching her face close off slowly.

“Your appreciation?” She repeats, a strange look coming over her face. Tim worries for a moment she’s going to snap on him for something as simple as asking for a name.

Tim opens his desk drawer, watching her tense, only to pull out a stack of blank Thank You cards and envelopes.

“Yes. My appreciation. People don't have to give my card to anyone, so when they do, I like to go the extra mile for them.”

“You. You send people Thank You cards?” Her face freezes somewhere between shock and confusion, which Tim honestly shouldn’t find so cute.

“Shouldn't I?” Tim asks, confused. “I know it's a little old fashioned, but everyone likes something other than bills in their mail.”

“Sign me up,” Stephanie says, throwing Tim for a loop.

“Really?”

“Really. I'll need the Pick 4, the bundle you suggested. Toss Scarecrow in there as my final choice, and I'll be set,” Stephanie says decisively, giving him a large, genuine smile.

Tim does his best to keep his cool under the look of happy surprise Stephanie is giving him. He feels a slight blush rising up his neck, and is for once grateful he has to wear a collared polo shirt to work. He's not sure if what he's feeling is because a beautiful woman is giving him her undivided attention or because Batgirl was giving him her undivided attention. He turns back to his computer to print out a copy of the saved policy he had drawn up for her, trying to cover his flush. He glances over to Stephanie as he prints her a copy of his newsletter, and watches the way her eyes crinkle at the corners, as she reads it and laughs, and decides ignorance was bliss for the moment as to why Batgirl came into his office for insurance, and why Stephanie lets her hand linger when he passes her a pen.

--

Over the weekend, Tim decides that the twittersphere just isn't doing it for him anymore, and he's craving a spicy hot chocolate that he knows only one bodega makes right. He grabs his wallet, pepper spray, and collapsible baton before heading out.

While the quantity of self defense weapons would seem extreme for most other places in the city, Tim didn't lie to himself about where he was planning to go, and who he would be seeing on his quest to get hot chocolate.

His first few homes had been in the nicer areas of Gotham, appropriate for a young, well raised boy to live while the adults around him decided his fate. As he got older, and pushed deeper into the system, the foster homes had transitioned into group homes, and the Old Gotham district had transitioned into Coventry, and finally, the Bowery. It was when he was fourteen, and struggling to show emancipation and a Wayne backed scholarship was his best way out to his caseworker that he found his diamond in a coal mine that did Cuban coffee in the morning and Mexican hot chocolate at night.

He walked up and waved to the young lady working the drink window, and placed his order for six hot chocolates and five orders of tea cookies to go along with them. Struggling slightly with his cumbersome load, Tim hurries a few blocks over to an alleyway where he knows at least two of his best marks work. It’s a long strip of concrete that runs between a cluster of old warehouses, and Tim keeps an eye peeled for anyone lurking in the dark, closed off side doors or hanging out behind a few industrial garbage cans.

“Anyone interested in something to drink?” Tim calls out as he hits the other end of the alley, and is soon beset with a few very thirsty working girls.

“Didn't think we'd be seeing you so soon,” Lina says, taking the cookies from him and passing them out to the other girls.

“It's been a few weeks hasn't it? And I wanted something sweet,” Tim shrugged as the girls begin picking at their snacks.

“I could give you something sweet,” Lina winks at him, making Tim laugh.

“Maybe another time.” It's his standard answer to them, as they know he'll never partake. “No Mel?” Tim asks as the tray makes it back to him with two unclaimed drinks and a bag of cookies.

“Already picked up, but she'll be back soon,” Lina says, sliding the leftover cookies into her small bag. “I'll make sure she gets your treat,” She smiles as Tim grabs a cup for himself.

Lina is the oldest of the women working that evening, but Mel has always been his best contact. He'd known her for years, when they would spend all day at the library, both escaping their homes until they were kicked out at closing. She had been the one to turn him on to the ladies of the Bowery for information, and he had been the one who made sure they all had city health insurance and renters for the ones with more permanent addresses.

“We all know she's your favorite,” Anna calls out from where she's working at the end of the alley, making the women laugh as Tim shrugs at their good-natured ribbing, grabbing his drink from the tray.

“Guilty. But that doesn't mean I like you all any less. Anyone having any problems with their paperwork lately?”

“Yeah,” Anna calls out from the perch she's taken in a low windowsill, “My premiums went up again! Thought you said the Waynes handle that shit,” She says, giving Tim an annoyed look.

Tim frowns at her while she sips her cocoa, “The foundation does. I'm in the office on Monday. Bring everything they sent you and I'll pick through it, see where they messed up.”

Anna nods, still not smiling at him. “Thanks. And speaking of paperwork,” she stands, and walks closer to Tim, “found out some guys are getting out early on ‘good behavior’.” She tries for mysterious, making Lina snort.

“If you're talking about those Two-Face thugs, everyone knows that.”

Tim had not known that, but winks at Lina when she looks in his direction. It's how they play this game. Tim plys the women with treats and free paperwork advice, keeping them as covered by the law as he can, and they pay him in gossip and making sure he's the only one they buy any kind of insurance through. It keeps them all safe and happy.

“Bet you didn't hear about Penguin being interested in that traveling exotics show that's coming to the museum soon,” Coraline pops in with. She's by far the youngest, and whenever Tim sees her he wants to wrap her in a blanket and call someone's parents to take care of her. But when Tim had offered to get her set up in a halfway house and apply for a grant, she had scoffed and refused to talk to him for months. That she is now shows she's forgiven him for what she took as his pity.

When they all look at her in surprise, she shrugs and pops a cookie in her mouth, “What? One of my regulars works for him, and forgot I was in the shower.”

“Why the exotics show? Sounds more like Catwoman than Penguin.” Tim asks, and Coraline just shrugs in response.

“No idea. My date wasn't exactly the brains of the operation,” She calls out as she walks away towards a car that pulls up near her. Tim makes sure he's off to the side, inconspicuous so that the johns won't see him, and vice versa. She gives a quick wave to Anna, the closest to her as she hops in the car. Tim watches her drive away, and Lina shoves her elbow into his side.

“She's old enough to make her own choices. Anna looks out for her.”

“Is she?” Tim mumbles to himself. A cold wind cuts through the alley, making him shiver in his thin hoodie. Lina rolls her eyes at him and shoves past him towards the street, closer to Anna and grabbing the lone cocoa from the drink holder and taking a big swig.

“See you soon, honey. Don't be a stranger. And definitely don't forget the cookies,” she waves as she walks towards the street. Tim calls his final goodbyes and starts his trek through the long alley and back to his car. He walks faster now, not laden with so many easily spilled cups and is almost at the main road when someone snatches the back of his hoodie and hauls him farther back into the dark alley.

Tim reacts as quickly as he can, dropping his drink and sliding his baton from his front pocket, extending it with a quick wrist snap. As he’s pulled farther into the dark alley, away from the lights of the main road, he whips his arm around fast and aims with the baton blindly for what he hopes is a shoulder or head. If he can get them to loosen their vice-like grip on his hood, he can pull his mace and impede them enough to run back to the girls and get them to move before his attacker runs into them.

He hits a helmet. The snap of his baton against it does get the hand to loosen as the man's helmet tilts back from Tim's mad attack. Tim slips a little, barely keeping his footing thanks to the force he put behind his swing, but the man's grip, switching from his hood to his upper arm quickly keeps him upright. Tim reaches for the mace in his pocket, though it looks like it may be a useless effort. The man doesn't move, other than to finally loosen his hand from Tim's arm and bring it to the side of the helmet Tim hit.

Tim is sure that later, once he's home safe in his bed, he'll have the existential crisis one has when they realize they just nailed the Red Hood. If he makes it back.

“What the fuck, kid?” the voice modulator removes any tone that Red Hood may have had, but Tim is sure it's either shock or anger. “Is that a nightstick? Can civilians even have those?”

“It's a baton and of course we can,” Tim snaps, unthinking. “And what do you think is going to happen when you attack someone in an alley?”

“Shooting usually,” he says, stepping closer to Tim, and honestly Tim had though 'looming' was something that only happened in poorly written romance novels, but here he is, being loomed over by the Red Hood.

“What do you think you're doing here?” Red Hood asks Tim as he backs him into the wall of a warehouse.

“Talking with the girls? Is that a crime?”

“Talking? No. But you weren't just talking to them. You were bribing them for something. What?”

“None of your business?” Tim responds, stepping to the side, which he knows he only does because the Red Hood allows it, and tries to get closer to one of the streetlights.

“Wrong answer. And don't bother trying to run.”

“Aren't you supposed to be one of the good guys or something?” Tim snaps, still in shock from the attack. “Isn't there a mugging or an assault you should be stopping? Are you really going to waste time interrogating a guy who brought some women hot chocolate on a cold night?”

“Hot chocolate?” Red Hood says slowly, not even the voice modulator able to keep Tim from hearing the scoff in his voice.

“Yes,” Tim points to the cup he had dropped when Red Hood grabbed him. “Hot chocolate. Some cookies. You know, nice things for some nice ladies.”

“There's been some guys hanging around, trying to recruit girls into pimping and running drugs. Thought you might be working with one of them.”

“Well, I'm not,” Tim snaps. “Now, if you'll excuse me, it's cold, I'm tired, and I've just been attacked by the Red Hood, so I'd like to go home now.”

“Jesus, calm down Tim,” Red Hood says, backing up and leaning against a warehouse wall. “Couldn't see who it was talking to the girls. Can you blame a guy for jumping to the wrong conclusions? And only the ladies get cocoa? I'm hurt kid, thought you said I was one of the good guys or something.”

“Sorry, didn't sync your looming schedule up with my chocolate delivery schedule. I'll reprogram my PDA.”

“You're a riot. Stay out of the area until this is all cleared up. And if the ladies tell you anything about these guys, let me know.”

“How? Should I build a Red Hood signal? Back light an Uzi in my living room window just for you?”

“Bedroom window would be my suggestion, your choice. But seriously, stay out of the area. Some weird shit is going down,” The Red Hood points at Tim, ignoring Tim's “Come on, it's Gotham,” to continue, “So stay out of the Bowery.”

“Sir, yes sir,” Tim says, collapsing his baton and shoving it back into his hoodie pocket as Red Hood walks past him.

“Watch the sarcasm, you know what it does to me. And I'll be on the lookout for your Uzi in the sky,” Red Hood calls, shooting his grapple and soaring up to the roof of a warehouse.

Tim hurries out of the alley and does his best not to break into a full-on sprint back to his car. This wasn't his first run-in with the Red Hood. Wasn't even his second. If it happened in the Bowery or Crime Alley, Red Hood probably knew. So when Tim had begun going around, trading information with people, Red Hood had found him. He had also let him go when he realized that Tim was not only completely harmless compared to thugs he was used to taking on, but Tim was supplying the lower class with affordable healthcare and business grants, thanks to a few loopholes Tim had found in the Wayne Foundation bylaws. It was also not the first time the Red Hood had flirted, but from what he had gathered from Lina, it was how he spoke to everyone.

Tim takes a moment to breathe a sigh of relief that Hood hadn't been anything more than shocked by Tim actually landing a hit on him. It could have gone a lot worse tonight if Hood had taken it as anything other than self-defense it was. He heads home, and definitely does his best to not think about how one would shadow light a Hood signal.