Roberta “Bob” O’Malley 

Every family has a figure who seems born to break the mold and define a new era. For the O’Malleys, that figure is Roberta O’Malley, better known as “Bob.” In a clan dominated historically by grizzled uncles and patriarchs, Bob has emerged as a central, formidable presence in the modern story. She represents a bridge between the old-school O’Malley way and the new-world opportunities (and pitfalls) of the 21st century. What follows is a profile of Bob O’Malley, in all her complexity: 

Presence: Bob is in her mid-thirties, with the kind of magnetic swagger that’s hard to quantify but impossible to miss. She’s of average height, but carries herself tall. Her style is a calculated blend of disarming and dangerous—leather jacket over an expensive silk blouse, old faded jeans paired with Italian leather boots. She has scarred knuckles from fights long past, which she doesn’t bother to hide with gloves or makeup. Those scars are like merit badges of experience. Bob has a habit of chewing gum even at the most inappropriate times (a family funeral, a court hearing), which gives her an air of casual defiance. And then there’s her laugh—often described by those who hear it as surprisingly warm and musical, a charming giggle that seems out of place given her reputation. But that laugh can also send a chill down the spine, especially when it escapes her at moments of high tension (more on that later). People meeting her for the first time often find themselves drawn in by her easy confidence, only to realize later that Bob was assessing and sizing them up the entire time. In any gathering, she has a knack for quietly taking control of the room without overtly commanding it—an arched eyebrow here, a soft chuckle there, and suddenly everyone finds themselves orbiting around Bob. 

Formation Years: Roberta grew up steeped in O’Malley lore and law. She was just a child when Dermot “Deals” O’Malley, her great-uncle, was still alive and holding court at Sunday dinners, recounting the old tales. From an early age, Bob learned that in the O’Malley family, silence can be a weapon and words are used sparingly but effectively. Around the kitchen table, she watched her father and uncles (the sons of Dermot) debate strategy and swap stories in a kind of verbal shorthand. As a little girl, Bob would quietly observe the adults, absorbing lessons that weren’t exactly meant for young ears—how to tell when someone is lying by their eyes, how a polite gesture could be more threatening than a shouted insult. She also learned the family’s golden rule: respect is to be taken, not requested. If she wanted a say in the family business, she’d have to earn it. 

Bob had brothers close in age, and their childhood was a constant contest of wits and wills. In the rough-and-tumble play of siblings, Bob quickly proved she could hold her own. If an older brother tried to boss her around because he was a boy and she a girl, he’d quickly find his pockets mysteriously emptied of allowance or his favorite records missing from their sleeves—Bob’s subtle reminders that underestimating her came at a cost. By her teen years, she was actively included in some of the family “errands” typically reserved for the lads. She served as a lookout on a couple of late-night dealings and proved both calm under pressure and clever in a pinch. Her father once sent Bob and one of her brothers to collect an owed debt from a local shopkeeper—thinking the shopkeeper might be less inclined to cause trouble with a young woman present. The story goes that the shopkeeper tried to flirt his way out of trouble, making a crass comment. Bob responded by very calmly locking the shop’s front door and suggesting her brother take a walk around the block. Ten minutes later, she emerged with the full payment and the shopkeeper’s dignity in shreds. When asked what she had done, Bob simply replied, “I reminded him that an O’Malley lady is still an O’Malley.” It was the last time anyone in the family doubted whether Bob had the stomach for the family business. 

The European Years: In her early twenties, Bob O’Malley did something unexpected: she left Ireland. Some say she needed to get out from under her family’s shadow to truly come into her own; others whisper that a behind-closed-doors disagreement with her father or one of her brothers prompted her departure. Whatever the cause, Bob spent the better part of her twenties moving through Europe like a shark through water—purposeful, always moving, and always looking for the next opportunity. 

She popped up in Spain running a short-lived but profitable scam selling “distressed luxury yachts” that didn’t actually exist. By the time angry buyers realized they’d been had, Bob was gone—sunning herself on the French Riviera under an assumed name, turning the proceeds into seed money for her next venture. In Prague, she insinuated herself into the confidence of an art dealer suspected of trafficking stolen paintings. She played the role of a wealthy, bored Irish heiress to perfection, all the while gathering information. When she abruptly left the city, the dealer found that three of his most prized (and illicit) pieces were missing, along with Bob. In Berlin, she’s rumored to have orchestrated a daring data heist with a crew of young hackers she charmed in the nightclub scene, lifting secrets from a pharmaceutical giant. That pattern repeated across Europe: Bob would enter a new city under a new alias, quickly find the underworld’s nerve center, and plug herself in. She learned to speak French, Italian, and a passable Czech, switching tongues as easily as she swapped identities. Crucially, Bob also learned the fine art of timing—when to get in, and when to get out. She always left town before the authorities had her in their sights, or just as a partner in crime was starting to wonder if he needed her around. By the time Bob finally returned to Dublin, she had a Rolodex (or rather, an encrypted phone directory) full of international contacts: fences in France, forgers in Belgium, a dockmaster in Greece, even a disgraced banker in Switzerland. She brought back a wealth of experience in cons, schemes, and the nuanced psychology of crime across cultures. In short, Europe finished the education that growing up O’Malley had begun, turning Bob from a talented amateur into a consummate professional outlaw. 

The Cigar Affair: Bob O’Malley’s European adventures greatly boosted her reputation in the family. Riding that high, she spearheaded one of the O’Malleys’ most audacious schemes upon her return—and in doing so, learned one of her hardest lessons. The scheme is infamously remembered in the family as “the cigar affair.” It started innocuously enough: a niche opportunity in high-end smuggled goods. Cuba produces the world’s most coveted cigars, and trade restrictions made them incredibly lucrative on the black market. Bob’s plan was to import a large cache of Cuban cigars into Ireland and then funnel them into the elite lounges of London and Dublin at a hefty markup. It was supposed to be quick, clean, and very profitable. 

Leveraging her contacts, Bob arranged for shipments through a circuitous route involving a bribed customs official in the Canary Islands and a trusted O’Malley cousin with a freighter. To cover their tracks, they set up a shell import company dealing in “exotic teas and spices” (with cigar boxes cleverly mislabeled as innocuous goods on the manifest). For a while, everything went according to plan; too well, in fact. The O’Malleys started making real money, and that’s when two things happened: competitors took notice and so did the authorities. A rival smuggling outfit, feeling the pinch in their own cigar trade, tipped off an international task force that something was fishy with those tea and spice shipments. The task force put the pieces together and targeted one of the O’Malley warehouses believed to hold the contraband. 

Bob smelled the trouble coming a split-second before the hammer fell. Rather than lose the goods and face a slam-dunk prosecution, she made a characteristically bold move: one night, an ominous blaze lit up the sky over the warehouse district. By dawn, the warehouse (and the incriminating stockpile of cigars) was a smoldering ruin. Bob had torched her own operation to destroy the evidence, betting that insurance and a lack of physical proof would be preferable to a criminal trial. It was legal high-wire act, but it almost worked. The insurance did pay out handsomely for “fire damage to legitimate inventory,” thanks to some forged paperwork and a little polite intimidation of the claims adjuster. That part of the plan bolstered the family coffers as intended, and for a brief moment Bob thought she’d snatched a kind of victory from the jaws of defeat. 

However, the authorities weren’t entirely fooled by the fire. An investigation followed, and soon Bob found herself facing charges related to smuggling and fraud—the evidence was circumstantial but substantial. Enter Judge Reginal Blackheart. Bob’s case landed in his courtroom, and if there was ever a jurist disinclined to cut an O’Malley any slack, it was Judge Blackheart, unless he was rewarded for his 'due- diligence'. The trial was a sho-piece  tense, dramatic and covered on prime time TV (good for all involved; Legends are forged  on the 6 O’Clock news), with Bob sitting at the defense table in tailored business attire, looking for all the world like a wrongfully accused entrepreneur. She was charming on the stand, acknowledging that yes, she dabbled in imports and had terrible luck with that warehouse fire, but no, she would never be involved in anything so underhanded as smuggling contraband. The jury was taken with her—accounts from the time suggest a few jurors were visibly charmed by Bob’s wit and poise. It was later discovered  that Jury tampering had been instrumental in her release.  However doom loomed.  

The Cuban cigar caper 

Having been released after the court case collapsed  she cooly lite and smoked outside the Dublin's High court. She had insured the cigars and sucessfully prosecuted the case against the insurance company.  After all they didn’t specify that she shouldn’t and after all she was only using her property for its intended purpose- nothing untoward there.  She argued successfully that each cigar’s destruction constituted a compensable peril.  Having taken the money , she was immediately charged with Arson and was unable to use the services of Masters, Crooke an Toole (who had quickly relocated to Patagonia) and could no longer defend her, even though she was a guilty as sin (she sheds sin effortlessly with the confession or a Cosmo, shaken not stirred).  No Jury this time, No Judge Reginal Blackheart to protect her.  She is doing time.  The talk on the street says brillant but to far.