Fanon:Roscoe P. Goldchain

Roscoe P. Goldchain was an Elder Sim living in Pleasantview as the town's top Mack and Crime Boss, and was the leader and founder of the criminal group known as The Organization. He is now deceased.

Family and Background
Roscoe's parents gave birth to Roscoe Riley and Terri Riley quite some time ago. Roscoe and his older sister, Terri, grew up without much money and had to live on hard times. His sister, Terri, eventually married a Rich Sim (and later completed the Gold-Digger LTW) and they gave birth to two daughters, Berry and Tamara, Roscoe's two nieces. Roscoe grew up to enter a life of crime after a tumultuous childhood and teenage experience. No one knows what for sure drove him into a life of crime, but it could've possibly been an abundance of intelligence, willingness to do bad things, desire for easy cash, and observation of an inept local police force. Roscoe is the Uncle to Tamara Riley of Moonlight Bay and is the Great-Uncle to Gary Gellar.

History
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. This truce was organized by the Flynn family of Moonlight Bay, the biggest criminal rivals to Roscoe's empire.

As soon as Johnnie/Marvin, the undercover cop, gathered all the info needed to take down Roscoe, the police began preparing for the big sting. But the news was leaked to the media, thanks to investigative journalist Christina Lin and Tamara was able to figure out that it was her uncle Roscoe who was behind the biggest criminal empire in the city. Roscoe, meanwhile, had found himself in a deep depression and was ready to settle down and hand over control of his company to Anna, Lance, and Bill, following Anna and Lance's wedding and honeymoon that was coming up. Roscoe met with two representatives from the two other rival crime factions in the city. Thanks to the undercover officer's work, the police would know when and where to take down not only Roscoe, but two other criminal organizations, as well. Unfortunately, the police was not aware of the meeting really being a coup for the other organizations to seize control from under Roscoe. Everyone knew if he was taken out, the rest of The Organization would fall, as well.

On one fateful night, a year and a half ago, everything aligned around this one meeting. The police sting, the bomb set to go off in Roscoe's meeting spot setup by his rivals, Roscoe handing control of his empire over to Anna, Lance and Anna's wedding to follow later that night, and Tamara confronting his uncle on all the lying and illegal activity he's been involved with over the years. The plan was for Roscoe to negotiate a truce between his rivals, put Anna in charge and make her the new leader of The Organization (affectively promoting her to Level 10 of the Crime career) in secret to his enemies, and retire off in peace and enjoy time with his niece, Tamara. However, nothing that May night went according to plan. The police raid wasn't expecting the other criminals to plan to take out Roscoe, which complicated their plans, and lead to a Police-Criminal stand-off in the basement parking garage, below. The lack of security, which to be deployed for the unexpected police raid, left Roscoe with fewer than usual enforcers, leaving Lance, Bill, and Anna to step in during the negotiations. Lance and Bill managed to enter the building, but Anna was stopped by Roscoe's niece, Tamara (whom the other thugs knew of, but very rarely interacted with, face-to-face). Tamara, livid and hurt, demanded to see her uncle, but it was Anna's job to keep anyone from coming in or out. The chaotic police/criminal standoff down below lead to the ones in charge of the explosives, the Flynn family, to go ahead with the plan earlier than expected, and around 9pm, the results culminated with a major blast that completely took out Roscoe P. Goldchain, and any others in the room during the talk. This sadly, included Lance and Bill Pinkerton, Anna's husband-to-be and brother-in-law. Anna herself, was only spared due in part, to Tamara's actions.

In the season finale, three major Sims were taken out, in the end. And at least three more (Anna, Tamara, and Marvin) had survived a very traumatic experience. About 13 Sims were estimated to have been taken out in the blast. Roscoe's criminal empire soon began to weaken, without a leader. Anna would've assumed the top position, but it was considered too much to bear in such a short time. And she also felt indebted to Roscoe's niece, Tamara, whom she owed her life to, and felt she had to keep safe. Anna and Tamara soon moved away from Pleasantview to Moonlight Bay, without ever knowing who it was that organized the explosion that night. In Moonlight Bay, Anna tried to hold down a 'normal' job, at the fast food place in the Downtown district, but soon found herself drawn back into the life of crime after meeting and becoming instant friends with Liara Kozen, a Moonlight Bay local who actually works in crime for the Flynn family, who unbeknownst to Anna, are the ones who planned the hit on Roscoe. Meanwhile, Tamara Riley tries to move on with her life, getting a mailroom job at the local TV station, and deciding she wants to become an investigative reporter to help keep the local public safe and informed about the local dangers in their community.