Roscoe started out like any other Young Adult Sim, looking to make his way in the world. He was never so great at book smarts, but was highly intelligent in street smarts, and was able to use this as a way to nter into the Criminal world. Roscoe started out small, with shoplifting and thievery. But he soon worked his way up to bigger and grander things, such as burglary and extortion. Over many years, his operation grew into a gang, and his gang grew into a criminal empire. Many came along, trying to compete against him, but his intelligence and experience always crushed any would-be competitors. Over the course of numerous years, Roscoe had a grip on the crime of Pleasantview. Operation in the shadows and with mostly-victimless jobs, Roscoe managed to stay under the radar for years, with 1/4th of all the criminals employed under him, with many of them not even knowing it.
About five years ago, however, the police force of Pleasantview started a huge operation to take down who they believed was the kingpin of all criminal activity in the region. However, Roscoe was smarter than the police force thought, and began to beef up his own security personnnel and clearance. At that time, he started using bodyguards and personal enforcers. Two who managed to catch his eye out of the dozens of indistinguishable thugs were Lance Pinkerton and Bill Pinkerton, two late-teenage orphaned brothers that had been fired from nearly every other Full-Time job in town, due to their (mostly, Lance's) ineptitude. Lance's natural charisma and schmoozing persona made him a valuable subordinate to Roscoe. And while Bill was too Good, his bigger brother managed to convince him it was either law-breaking or end up out on the street. Lance ended up being a good henchman and thug, but was bad at getting physical, while Bill managed to be a highly convincing interrogator 9mostly because he legitimately didn't want to get violent with any Sims). The two borthers rose through the ranks, up through the organization, but Lance decided to stop at being Roscoe's cheffeur and personal guard, considering he's kind of a Couch Potato and is far from being a Workaholic or Ambitious, in any way. The two brothers proved to be loyal thugs for Roscoe, but things really took off when Lance's new girlfriend, Anna Evans, was introduced to his life of criminal dirty-work. Unlike Lance, Anna was Ambitious, a hard-worker, and highly capable, athletic, and intelligent. When Anna was first introduced to the criminal world, she didn't know what to expect and was as cautious and worrysome as the next Sim. However, being a naturally gifted Athlete, as well as growing up poor, Anna proved to be highly skilled as a criminal, even at the bottom-level and was highly encouraged and motivated by her peers. The level of support she got, on top of the money, was enough to make her stay in the criminal organization. Anna Evans rose through the ranks even higher than her boyfriend, Lance, had, and quickly became The Organization's Most Valuable Sim. Roscoe might've seen her as a threat, if not for her being 100% loyal to the cause. So instead of taking care of a potentially new Crime Boss, Roscoe nurtured her and made her his top enforcer and bodyguard, pitting Anna as a Hitwoman (level 9 of the Crime career), only serving below Roscoe himself, and no one else. While Lance (level 4, Chauffeur Bodyguard) and Bill (level 6, Interrogator) enjoyed their newfound success and hefty pay, Anna enjoyed the support and encouragement she got from Roscoe, something she never got from her real father.
During this time, however, Roscoe's family were unaware of his criminal life and had assumed him to be a humble Pawn Store owner. This was easpecially the case for Roscoe's naïve niece, Tamara Riley. Roscoe had gotten visits from Tamara nearly every weekend and considered her the daughter he never had. After all, Roscoe's had many partners, but was always too paranoid to ever have a true girlfriend or wife, let alone bring a child into his kind of life. As Roscoe bonded with his niece more, an undercover Agency officer by the name of Marvin had infiltrated the Organization, and had even become Good Friends with Anna, Roscoe's second-in-command. As intel was being prepared for his big takedown, all the other criminals from around town had formed a temporary truce, in order to try to take down the organized crime giant.
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Roscoe P. Goldchain at home.
