The Life and Times of Jenny Calabrese

07 Nov, 2025

I had lots of plans for my character in Over/Under, Jenny Calabrese. Due to her untimely death, many of those plans were cut short.

One of my hopes as the Stratemeyer Syndicate's programs stabilized was to get "out of the office" and go roleplay with characters outside of the faction. I had started this a bit, but hadn't managed to get out by the time her story came to an end. As part of this, I had begun sketching out a backstory for her.

Jenny Calabrese was a lot of things to a lot of people: straitlaced villain, intimidating but inspiring boss, crush/romantic partner. However, as tempting as it was to lean into over-the-top corporate villainy, I knew I would be more invested, and be more interesting, if I played her as a full human with her own perspectives and justifications (even if they are skewed or incorrect.)

It was an interesting position to be in: how do I make a character that most people playing will ideologically, constitutionally disagree with (hell, that I disagree with) and make people come around to them? As a starting point, I gave her a number of admirable traits. She was calm and patient (even in the most frustrating of situations.) She tried to be understanding and empathetic, encouraging others to succeed and not focusing solely on her own success. She was honorable and mostly honest, preferring discussion over coercion, though that was slowly slipping away at the end.

On the other hand, she was a member of a faction that the very pitch document for the game labeled as the "bad guys." How could a person with good qualities, that had friends and ideals, belong to the designated villains? I wanted to give her reasoning behind her beliefs, rooted in her fictional history and experiences. Thus, the backstory of Jenny Calabrese was born.¹

Early Life

Jenny Calabrese was born on Callisto II, a remote mining colony run not by an interstellar megacorp, but by a two-bit planetary family company. By galactic standards, it was a small business, though it encompassed the young girl's whole world. The atmosphere was thick enough that the local star barely shone through, and no starlight shone at all. Most of the planet was rocky and unfit for habitation; the inhabited portions were mismanaged in the way only a small incestuous company could. The miners worked in unsafe conditions for an unprofitable business, and received the bare sustenance they needed to continue working.

Jenny was born to a single mother, Alicia. Alicia Calabrese was hardworking, well-liked, and clever, if not particularly well-learned. She herself had not grown up on the colony, but immigrated after facing unemployment on her homeworld. The demands of mining meant that Jenny was also raised by a rotating cast of aunts, uncles, and cousins, most of whom had no blood relation. Jenny never knew her father, and she told others that her mother probably never knew either. Without judgment, of course - Jenny admired her mother greatly for surviving and raising a child on Callisto II, and attributed much of her success to her mother's influence.

Jenny would remark to close friends that her mother could have been an entertainer, under other circumstances. Alicia loved telling her daughter stories. Her favorite tales were of their mythic ancestors, the origin of the name Calabrese. They were descended from a mighty culture of arctic warriors on Old Earth, she said, who sailed through the middle of the world in their dragon-headed battleships, until they reached the warm paradise of Calabra and built a utopia. Their princes and kings fought wars, traveled the world, slew dragons, outwitted demigods, and were always involved in the half-dozen other mythic stories that Alicia knew. She repeatedly insisted to Jenny that Calabra was real, somewhere out there in the deep black. Jenny herself would confess privately that she was unsure how much of her mother's stories were real, but as a child, she was enthralled. When she looked up to the smoggy skies, she could shut her eyes and imagine a universe beyond.

Alicia also taught Jenny more practical lessons. Be honest and straightforward, but know when to keep your mouth shut. Be kind where you can, but be firm where you have to be. Just because someone else wins, doesn't mean you lose. Most of all, Alicia told Jenny that no matter what, if she set her mind to something, and worked as hard as she could, she could achieve it. Jenny took all of these to heart and carried them with her throughout her life.

When Jenny was seven, the Stratemeyer Syndicate received the contract to install and run the autocreches for the education of miners' children. By the standards of any developed society, these "edu-boxes" were a horrifically poor replacement for real teachers and peer connections. Yet for Jenny and many of the other miner children, they were a massive improvement from the collective homeschooling by exhausted, injured, and occasionally abusive off-duty miners.² This minor change would alter the trajectory of Jenny's life.

When she was twelve, a revolution came and swept the planet.³ The union, formerly just barely tolerated, overthrow the hated company and slew the family running it. From now on, the planet would be ruled justly, as a worker's commune, with equitable distribution and fair treatment for all. There were idealistic plans in those heady days, but they soon fell by the wayside. The circumstances the new commune found itself in quickly eroded its revolutionary ideals.

Callisto II was not quite self-sustaining, and post-revolution just one emergency away from mass deaths. Worse still, due to the relative isolation of the planet, they had no contact with other communes or interstellar mutual aid organizations from which they could receive support. Instead the only regular contacts were the corporations purchasing ore and alloys. Faced with a dissolving coalition⁴ and a quickly diminishing supply cache, they took what seemed like a reasonable decision - continue operating the mine, and export its goods to keep the colony afloat.

At first, it was hoped that the new regime would still have a positive effect - instead of working for a ruling family, they were working for each other, and so would treat each other fairly and improve their circumstances. However, the slain rulers had left so little non-extractive infrastructure that immediate improvements were impossible. The supposedly innocent temporary solution became damningly permanent. The mines remained open, unsafe, and exporting for profit. The union bosses themselves grew quite comfortable, as their corporate trading partners plied them with gifts and favors. Within a year or two, the dreams of the revolution died.

This was young Jenny's first impression of union rule. The new boss was the same as the old boss. They had high wages, but everything cost more.⁵ The thugs who harassed Alicia because they reviled her were replaced by thugs who harassed her, they claimed, for her own good. Jenny remembered her mother coming home at least once a week from a union meeting, sobbing. One of her first jobs as a child was in a foreman's office running numbers, and she saw firsthand how little the corrupt bosses had improved anything.

The worst disaster struck when she was 14. The mismanagement of the bosses allowed food caches to whittle down until they were wiped out by a fire.⁶ They insisted the mine operate even as the colony went hungry. Jenny referred to that time as the Long Summer, and refused to speak of it to coworkers.⁷ Later in life, Jenny encountered unions of a far higher caliber, but every time her mind would go back to those days of disillusionment and hunger. She would negotiate politely, treat them kindly, but remained wary, just waiting for the other shoe to drop.

Education

Early Schooling

Jenny continued to excel in the Stratemeyer autocreches. When she began the secondary-level curriculum, several talent acquisition algorithms had already taken notice. Around the time of her graduation, she received a letter with a full-ride scholarship to Cobblestone University, one of the schools Stratemeyer used to foster executive talent.

Jenny was reluctant to go, and when she expressed this Alicia almost killed her on the spot.⁸ For Jenny to deny herself an educational opportunity was not just foolish, it was unthinkable. Her mother validated her fears, confessed that she would miss her daughter more than anything in the universe, but told her over and over again that it everything would be fine, that she had a great opportunity, and if something like this came along she needed to reach out and take it. Over a tear-filled conversation, Alicia and Jenny poured out their hearts. By the end, Jenny promised to go to school and get a good education, and Alicia promised to wait for her. That night, Alicia announced that she was going to put some of her wages away every single day to buy a giant, fancy cake for university graduation. Jenny begged her not to, to spend the money on something more practical, but Alicia refused. It was her coping method, she said.

Jenny was whisked off to Cobblestone U⁹ and an entirely different world. She was suddenly thrust among corporate princelings, children of well-to-do officials, and academic champions from rich planets. She exceled in her coursework, but socially, she had a lot to learn. As she studied for her courses, she also studied fashion, manners, and accents. She learned which foods were acceptable to eat, and which ones were gauche; she learned to navigate the social minefields of executive outings; she learned the polite topics of recreational conversation. She learned the who, what, whens, wheres, and whys of wider galactic culture. She thought of herself like ore, slowly refining herself into a fine alloy that might one day serve a greater purpose.

And she enjoyed the refinement. The miners who raised her were fine people, but compared to her professors and fellow students, they were all just so provincial. Talking in office hours or in study groups, Jenny felt like she had been thrust into the universe she once only imagined. Things her classmates took for granted were new and exciting. She devoured information about space logistics, interstellar diplomacy, planetary finances, and anything else that helped her grasp the bounds of her new, vast universe.

Her goal was to blend in with her classmates as best she could, though she knew she'd never truly be one of them. Her classmates might have snickered behind her back at her lightly-stocked autocloset or her slips into proletarian verbiage, but Jenny knew that if she set her mind to it, and worked hard, she could graduate as a star Stratemeyer employee. Sure, she resented the fact that many of them got to coast and party while she studied to keep her scholarship, but there was no use complaining about it. Besides, if she proved herself academically, that was something they could never take away.

The miners of Callisto II disparaged all offworld corporations as nothing more than a bunch of money-hungry slick-haired automatons that'd slit their grandmothers' throat for one more credit. However, at Cobblestone (and later in the Syndicate) Jenny didn't find short-sighted cash-grubbing thieves. She found clever, driven people with plans measured in years and decades. She found teams of people, willing and eager to work together, share credit, and support each other. She found people building dreams; investing in businesses, products, or even whole planets to grow them into something even greater. She watched Stratemeyer investment and management expand availability of goods and increase economic output on world after world. Each was left with a wealthier economy, more jobs, and a more orderly society.

Jenny wasn't naïve. Stratemeyer collected its share of profits from its various investments, and often took a very active co-management role with the local government, when it didn't outright purchase subsidiary colonies. Cobblestone had educated her well. Stratemeyer was entitled to the profits of its investments because it risked its own capital. Stratemeyer only engaged in governance to protect its investments, but they clamped down on other forms of corruption and the criminal networks enabling them. From their self-interested action, they generated public good. They could at times be harsh, and Jenny vociferously protested in her classes at corporate brutality or ineptitude, but she never doubted the legitimacy of Stratemeyer's existence and control. Whatever methods they employed, it was hard to argue with the results.

Of course, great inequality persisted on Stratemeyer worlds, but didn't inequality exist everywhere, regardless of who governed? Jenny certainly thought so, the hated bosses and the Long Summer fresh in her mind. It was the unfortunate state of human nature, Jenny reckoned, that inequality would persist; better for it to be the least harmful inequality of meritocracy. Jenny knew Stratemeyer itself was not a meritocracy, but it was the closest she had ever seen. After all, hadn't a simple miner's daughter risen to the top through hard work alone?

Later Schooling

When Jenny was twenty, three years into her education, her mother died. She didn't even find out via a death notice, but by an automated request to update her insurance beneficiaries. Those frantic hours of calling and writing to see what had happened were also a formative memory. When she finally got an answer, she was in disbelief at its mundanity. Her mother died in a mining accident.¹⁰

When the authorities confirmed Alicia's death, she sat unmoving in her dorm for the rest of the day, and missed a test for the first and only time in her schooling. The day after, she began to pick up the battered pieces of her psyche, but she was not the same in her last year. She threw herself just as hard into her work, but spent less time socializing. This almost sank her during final assessments, but she was able to recover enough to succeed on her Networking final, and recover a few friendships that would prove important to her placement.

Jenny graduated Cobblestone University at 21 (after four years, not the three she hoped), and was immediately pulled into the Stratemeyer Leadership Advancement and Progress track, an honor given only to the top 20% of students in her class.

Internship

The First Internship

As the first step on the Stratemeyer Leadership Advancement and Progress track, Jenny was given the rank of Intern and assigned to an executive group lead by her first boss, a one Alexander Murray.¹¹ She joined him for a year finishing a massive merger with a planetcorp on Augusta VII. Her schooling might have prepared her for the technical aspects of being an executive, but this was the real deal, and there was no substitute for experience. What she learned the most was that in the real world, there was no right answer. In university, she could count on a correct answer existing, even if she just hadn't figured it out. Here, in the real world, there might not be a right answer. Understanding that was the difference between a promotion and a disciplinary hearing.

Alexander swooped Jenny under his wing. She admired her mentor greatly. He was cool, calm, collected in the face of the constant chaos unfolding around him. He didn't shout or demand, but moved people with his presence. He was as at home with in the intern bullpen as he was with the C-suite. He didn't have a wealth of technical knowledge, but made up for it with decades of experience and a strong understanding of everything his job touched. Jenny looked up to him, worked with him, even talked through her personal life with him.¹² Alexander took a liking to the young intern as well, describing her as "hungry", but with a sense of propriety that put her above the other cloying, rigid, and obsequious interns.

Alexander slowly doled out more and more responsibilities to the young intern, such that by the time the merger was completed, she was well known to the various departments and teams as Alexander's number 2. She struggled under the weight of these responsibilities, and as the merger was closing, considered requesting reassignment to an accounting subsidiary or some other low-intensity position. She privately worried that if she kept this up, she might not be able to prove herself and burn out. Some terrified part of her feared disappointing her mother and herself.

Alexander listened to her concerns and concurred. It would do her no good to burn out by jumping into an executive role so early. He offered her another option - served another internship term with him, on an assignment from beginning to end. She was going to refuse, until he mentioned the location - Callisto II.

The Second Internship

Callisto II, said the Stratemeyer market intelligence, was an opportunity. With a little bit of capital investment, the planet could be turned into a major hub of mining and refining for the subsector and support several other subsidiaries looking to expand. As Jenny, Alexander, and the management team were in transit, Stratemeyer profit acquisition platoons were already engaging in a hostile takeover. The union leadership was ill-prepared and offered little real resistance; the demoralized workers put up a token fight. When Jenny arrived, she saw the effects of corporate violence, but had little sympathy for the union loyalists. To her, they were just the corrupt bosses who failed to save her mother.

Alexander immediately leveraged Jenny's local connections to smooth over the transition process, a role that she was only too happy to take on. She was a true believer in the mission, seeing the Syndicate as salvation for a planet that had seen so much misery during her lifetime. She also figured that she was the person best-placed to protect her family and friends from any ill-conceived initiatives or crude punishments.

Jenny extolled the virtues of the Stratemeyer Syndicate, offering herself up as an example of what could come with compliance. She worked the elder miners, tirelessly discussing and soothing their concerns. When doubters persisted, she would remind them of the negligent governance and broken promises they had suffered under. A Long Summer would never happen again.

By the end of the assignment, Jenny had a wealth of experience, and a set of metrics to prove her capability. Profitability up, production rates up, and logistical costs down, of course, but Jenny was prouder still of the other metrics on the planet. Literacy rates and school attendance rates were through the roof, and several miners would be permanently transitioning to teaching at a newly-founded school system to supplement the autocreches. Hospitalization for illness was down well below pre-acquisition baselines. Most important of all, though, mine accidents were down 54%. Cutting them by over half was no easy feat, but Jenny spent many sleepless nights hammering out action plans and hounding engineers to do better. She firmly believed that long-term Stratemeyer control would continue to suppress accidents as the mine capitalized. Over the empty grave of her mother, Jenny left a slice of the most luxurious cake she could afford. As she walked away, she wiped her tears and told herself that even if she couldn't save her own mother, she had done everything she could to save someone else's.

Jenny wasn't just concerned with the metrics, of course. She was heartened to see that the whole planet had changed. People were living better through Stratemeyer. Prices for non-necessities had cratered thanks to Stratemeyer logistics, and luxuries young Jenny could only have dreamed of were now available planet-wide. There was a sense of greater purpose, she thought. An understanding that they labored not for some abstract market, but as part of the Stratemeyer team, helping carry out the vast projects undertaken by the company.

There were costs to the changes, of course. Just as in college, Jenny wasn't naïve, and knew that some things on the planet would be lost. Parts of culture, parts of their history. Intangible things. Jenny believed that these sacrifices were well worth the results. Yes, greater automation in the mine had forced miners out of their traditional work, but they would be teachers, service clerks, and logistics workers. Yes, it severed the traditional bond of the miners' brotherhood, but these jobs would be necessary as the planet modernized and diversified. Sure, the union had been banned and suppressed, but what good was a union that brought on the Long Summer? Besides, Stratemeyer was not the average megacorp. It had incentives to take care of such a productive workforce. The pay structure of Stratemeyer had created massive inequalities, but if that rewarded the next young driven girl with dreams of the stars, then any cost was worth it.

Ultimately, the experience fostered a sense of inevitability in Jenny. The corporation had ruled her world poorly; attempts to overturn that rule had been colossal failures. In her studies, she had watched as every alternative collapsed or became subverted. Nothing better demonstrated that than Callisto II, a horrific failure to exist outside of the corporate system. Eventually, the corporations, the only stable entities in the long-term, would come in and snatch up the worlds. Individual corporations would come and go, of course, but the system was inevitable. The choice was not between corporate rule and some alternative, it was merely what kind of corporation would eventually rule. It was the duty of people like her, she mused, to build better corporations, and best protect the people working in them.

It was like carcinization, she mused from her office window, looking out over her transformed home. Every planet that could support life eventually developed crabs. It was just one of the most efficient body plans in the long run. Everything else was minor deviations in response to temporary conditions. So too was the corporatocracy - the inevitable result of material circumstances, the final evolution of society that humanity would return to over and over again.

Despite her outsized contributions, her performance on Callisto II was not viewed entirely positively. When debriefed by headquarters, Alexander reported that Jenny had been a stellar worker, but at times, she acted in a manner inconsistent with the goal of ensuring the profitability of the Syndicate's investments. He noted a few occasions where Jenny butted heads with other members of the management team and even Alexander himself, passionately advocating for options that were not the most profitable in their project timescale, but seemed to benefit the consumers and workers of Callisto II. Even with these "outbursts", he determined that Jenny had been far more of an asset to Stratemeyer than a cost. He recommended that she be promoted into the junior executive bullpen at Central and stay there for perhaps a half a decade; long enough that she would shed attachments outside of the Syndicate and orient herself more closely to their goals.

Jenny never discovered this, and left Callisto II thinking she was about be rewarded with her first permanent outbound assignment.

The Waiting Time

Instead, Jenny found her self in the vast bureaucratic complexes that made up the underlevels of Central. Promoted to Junior Associate, she found herself in a tiny cubicle amidst a sea of other tiny cubicles, bouncing around from department to team to committee. She initially attacked the menial duties and repetitive assignments with the same enthusiasm she showed in her internships, but not even a year in they began to wear on her. Her work began to suffer, and she'd find herself losing minutes in daydreams at her desk. She acted out in little ways. Every cycle, she snuck her lunch back to her desk, so she could spend most of her break staring out of the closest window on her deck level.

She watched the stars that had been obscured to her as a child. She made a lot of silly promises to herself staring out that window: that she would visit every star; that she would find Calabra; that one day she would wear the stars in a dress. It kept her sane through the monotonous days, and as her not inadequate pay accumulated, some of those dreams came a little closer to reality. Still, Central was stifling. It was like she was back in college again, with every single other person deeply immersed in Stratemeyer culture; and yet worse, because instead of Cobblestone's energetic student dreamers she dealt with the contented, disgruntled, and incompetent people that never hoped to leave the bullpen. There was certainly no one there who dreamed as big as her.

She so desperately wanted to be back in the field. It wasn't until she was years into her time at Central that she truly realized how much she loved facing the public, talking with people who weren't Stratemeyer employees, and getting to know people so very different from herself. At the end of her second year, Jenny made moves. She leaned on the handful of friends and acquaintances she had kept after her university breakdown, getting her name out and listening for future opportunities. When an acquaintance mentioned an ongoing acquisition of a little station named Prospero's Dream, Jenny jumped at the chance. She brushed off warnings that it was a small operation, with little glory to be won. She was just eager to finally be out in the world.

The Dream

Jenny Calabrese arrived on the Dream bright-eyed and full of energy, excited to finally receive a permanent assignment as a full employee. It was over three and a half months since her birthday, but she promised herself she wouldn't celebrate until she landed. She quickly proved her managerial ability to the C-suite of the station's subsidiary. She was duly promoted to Strategic Operations Integration Manager, and then to VP of Operations. In the hierarchy of the subsidiary, she sat above all other management, and just below the C-suite, responsible for turning their directives into action. A week in, she was put forward as a new boss for the Syndicate; later that day, she died.

Notes

I'm not going to detail the event's of Jenny's time on Prospero's Dream, as I feel that's a story better suited to when the dust has settled. Besides, it isn't finished being written. My understanding is that due to several personal relationships she formed, she still haunts a few of the Dream's denizens.

I took some aspects of this backstory from real people I've met. I think I've sufficiently fictionalized and mixed them up that it is no particular person.

The version of Stratemeyer here is my own, and is not necessarily the one in Over/Under, and most likely not the one that's in A Pound of Flesh. However, if you like it, you should use it. I think it can be interesting for characters to have an easy way out with a "lesser evil." It brings questions of morality into sharp relief, especially if and when Stratemeyer proves itself to be not so different from the other megacorps running around.

I am under no illusion that Jenny Calabrese is a hero, even if she thinks herself one. She is part of a system that breaks people, breaks cultures, and breaks worlds in service of funneling profit to a tiny handful at the top. Jenny imagined a better world, but she never could imagine overturning the systems that cause so much of the pain in the first place. Maybe that would have changed over the course of O/U; maybe it wouldn't have.

When I was entering Over/Under, I picked the Stratemeyer Syndicate because they were the clear underdogs. Most characters and players hated them from minute one and would not reconsider. I wanted a challenge, I wanted something less popular, and I wanted a faction that I wouldn't feel too bad about if it ultimately lost. I could have gone for an overtly evil corporate suit, cackling over arbitrary punishments and hideously inefficient villainy. I decided pretty quickly that character just wouldn't stand the test of time. It was two-dimensional, and while it might make the occasional good foil to another character, it is not something I would have a long term interest in playing.

I also didn't want a character who planned to jump ship from day 1. There were people who played characters in Stratemeyer purely to get them out of Stratemeyer, but that route was unappealing to me. What was the point of supporting a beleaguered, challenging faction if you were planning on leaving? I'd short-circuit my own challenge. The alternative, creating a loyalist for the bad guy faction, seemed far more interesting.

And I wanted to see if I could make other people loyalists. The evil megacorp was never going to be popular, but I wanted to see if I could build something that people would at least find interesting than Puppykickers Inc. My aim was for something like LexCorp of the 2025 Superman movie: a company of people, smiling and genuinely enthusiastic, doing dastardly deeds for an evil boss because the working environment is healthy and the benefits are great. I was told after the fact that the feeling was "What if The Office took place at Lumon," and I will take that as a win.

Biased as I am, I do think Jenny is an interesting character. I think she would have gone on to interesting things had she survived, but O/U is a multiplayer game, and everyone else gets a say. I think she could serve as a good antagonist, and maybe a very different antagonist from usual megacorp executives. I know she touched a lot of people, and I'm eternally grateful that I could bring something enjoyable to a table with so many passionate, creative, and skilled players.

I'm going to miss her.

#character #lore #over-under #rpg #worldbuilding