On the other side of Ponyville, away from the School of Friendship, Roberto Silano stood in front of the Ponyville Schoolhouse. It was a small red wooden building that looked pretty much like how you'd imagine a typical schoolhouse to look, right up to the small belltower. The one thing that made this stand out from your typical schoolhouse was the heart patterns that are painted and etched onto literally every nook and cranny, from the windows, the entrance, and even the weather vane atop the belltower. It gave the school a very girly look. Roberto noticed that these ponies seemed to really loved girly designs, but considering the larger female population, he supposed it made sense.
It certainly made Roberto wonder how much violence he would allow his business to commit here. Roberto was a crime boss who always tried his hardest to keep any women and children out of he and his business's affairs, that was one of the reasons he and his wife, Isabella, slept in seperate rooms and her room had no windows, in case anything like an assassination attempt were to happen to him. It was a difficult code to live up to since none of his henchmen, even Gabriele, ever cared much about the safety of women and children, and would gladly kill them without question if they had to. And considering how nosy women and children could be in this day and age, that code had to be broken quite a few times whenever some dumb wannabe journalists and internet kids who thought they were much braver than they actually were decided to fuck around and think they could be much more clever than guys who have bribed and even killed professional journalists far more competent than them hundreds of times.
While Equestria isn't exactly short on stallions, mares did take up a majority of things around here, with the exception of the Royal Guard who until several years ago have been mostly male-dominated, and also most jobs that required more physical labor. Roberto was slightly relieved by that because if a male couldn't help protect and assist physically, then what was the point? Though these are ponies, not humans, so he figured he shouldn't get too worked up about it. Roberto figured that unless the mares were mothers of young children, he could allow violence and murder upon them, as the mares here were just as capable, if not more capable than the stallions. Plus, Equestria was a very egalitarian land anyway, so it probably wouldn't be shamed as much as it would be back on Earth.
Roberto continued watching the school, quietly smoking his cigar while leaning slightly against the short roadside fences. It was late afternoon, and already a full hour since he left his sons back at the School of Friendship, as he had other things he needed to do after looking around over there. He could only hope Gabriele did not cause too much trouble while he was there, as he knew that if Gabriele was forcefully thrown into a situation he didn't want to be in, he will cause some disaster to happen, which was why it was always a good idea to have Ainsley accompany him to keep him in check, because if he was on his own, Roberto could only imagine what would happen.
He thought it was a good thing leaving his sons alone with the ponies again, as the further the friendship between them is strengthened, the better the chances of Roberto and his family will have in not only gaining Princess Twilight's friendship, but also turn their backs to Silanos' illegal businesses and if possible, get as many resources they need for their business should they ask Princess Twilight or the Council of Friendship for them. Equestria was a land of infinite possibilities that they knew nothing about, so it was necessary to get all the help they could, especially to cement their power there in case any other crime families and groups decide to come along.
When the portal between Earth and Equestria opened and they officially partnered up, Roberto was the first to decide to expand his businesses there. All the other mob bosses and heads of other crime families, as well as leaders of none-Italian gangs, did not dare to expand their businesses to Equestria. They thought it was not worth the risk, because Equestria is a very alien world that did not function like human societies, and they did not think that magical horses would make good customers or associates, especially after Princess Twilight's whole sappy speech about friendship that she gave at the United Nations, which told the other bosses ponies would not be compatible with their businesses. So they all decided to play it safe and keep their businesses back on Earth where it was guaranteed to at least not end in complete disaster, since they felt humans could be trusted with their businesses a lot more than ponies, especially when it came to narcotics.
But Roberto was someone who believed that when it came to business, if you didn't adapt with the world around you, you'll get left behind in the dust and buried. Roberto always believed in taking risks and being progressive, maybe even bending the rules a bit, if it meant keeping the business alive, which was ironic since outside of work, Roberto was the most traditional and old-fashioned Italian you could come across, but he was willing to make an exception for his son, Ainsley.
The only other boss besides Roberto that actually expressed some interest in expanding business to Equestria was none other that his biggest rival in the mob underworld, Don Giorgio Cicchino. Don Cicchino was a short balding tan-skinned wine-bellied man with a pencil mustache, and his high-pitched raspy voice sounded similar to a cartoon character. He was a very ruthless mob boss, much more than even Roberto, as he ruled all his businesses with an iron fist and made sure he struck fear into everyone who worked for him, and anyone who even thought of stepping out of line got killed immediately. Cicchino ran his own wine-selling business, and his illegal businesses mostly included the gambling business, but his biggest was easily the prostitution business. Cicchino was a straight-up pimp.
Despite Cicchino being more ruthless than Roberto was, he has always been far less successful, since as Roberto said to Gabriele, getting people to fear you was only half the battle, you needed to earn their respect to, and barely anybody truly respected Cicchino. The rival don harbored a deep resentment and jealousy towards Roberto because of how much more successful Roberto was than him, which was helped a lot by the fact that Roberto was heavily involved in the narcotics business, which Cicchino never got into since he did not want to take the risk of one of his henchmen rotting their brains and end up getting arrested and then ratting him out to the authorities, thus destroying everything he worked so hard to build. Roberto was not particularly fond of Don Cicchino either, as Roberto has never been a big fan of the prostitution business, and the way Cicchino treated all his workers did not help either. Cicchino had a lot of sex workers, but he paid them very little money, he was known to bed many of his workers, very often against their will, and despite being against the drug business, for some reason he was perfectly fine with getting his workers hooked on drugs and alcohol as part of their payment in order to keep them dependent on him and they would not stop working for him. It wasn't like walking away was an option anyway, since anyone who tried would get killed immediately, either by a staged robbery or by purposefully overdosing them, so that no one would suspect a thing, if they even cared enough to suspect anything at all.
When both Roberto and Cicchino announced their interests in going to Equestria, Cicchino wasn't exactly happy hearing the fact that his more successful rival had the exact same idea he did, and he certainly made sure Roberto knew exactly how he felt as all the attention in the meeting of all the crime families were drawn to the two of them, but Roberto didn't bother wasting his breath on him. When it came to the rivalry between the two of them, Cicchino was more bark than bite despite his reputation, as despite the fact they were enemies and hated each other, they always tried to avoid killing each other as a war between the two crime families would be bad for business and end up doing more harm than good.
Roberto, naturally, ended up beating Cicchino by traveling to Equestria and set up business there first, which Roberto could imagine Cicchino was not happy about. By the time Roberto and his family were setting up business in Canterlot, Roberto had gotten word that Cicchino had arrived in Equestria as well, and was setting up his business in Manehattan, which Roberto already got to first. Apparently, aside from successfully opening up his wine-selling businesses, Cicchino had even started not one, but two prostitution businesses there, one that hired human men to sleep with pony mares, which proved to be pretty successful due to the low male count in Equestria so there were many mares who were more than happy to hire out their own man to satisfy their needs, and the other one was a smaller one that hired mares to sleep with human men, usually important men who could never be hired themselves. Roberto was honestly very disgusted by Cicchino's new business, as if prostitution wasn't enough, Roberto found the idea of humans sleeping with horses to be extremely deplorable and sickening, and he had no idea what man in his right mind would ever find these colorful ponies to be sexually attractive in any way.
Now that Cicchino has established his wine and prostitution business, the only thing left was the gambling business. Recently, Roberto got word that Cicchino was thinking of building a casino (that doubled as a hotel that Roberto couldn't help but feel might be used for trafficking purposes) in Las Pegasus, which Roberto happened to also be planning to do, and Roberto had a strong feeling he would get to Las Pegasus first just like he did everything else Cicchino wanted to do because Cicchino spent more time trying to keep his workers in their place by beating them around rather than being an actually smart businessman.
After Roberto thought about all those things concerning Don Cicchino, Roberto now couldn't help but feel a strong sense of suspiscion that Cicchino could be behind the assassination attempt against him in Sugarcube Corner, as if there's anyone who wouldn't pass up the opportunity to kill off his main rival in such a way that could never be traced back to him. But while Cicchino had the motive, that still left the means and opportunity. With opportunity, Cicchino definitely had a high chance of having it, as Cicchino could've just sent many of his men to all the different places that would set off the Cherry Incident at any time, so that meant he had the means too. Although, Cicchino could only have had half of the means, since that still left how Cicchino would have even known Roberto's schedule in order to time all the chain of events precisely to when he'd enter Sugarcube Corner. That reinforced Roberto's hunch that the only way Cicchino could have pulled this off is with someont on the inside, someone who has betrayed Roberto. But first he needed to properly confirm his theories, and the first thing he wanted to do was talk to none other than the teacher of the three fillies who caused his choking in the first place.
Why did their teacher release them early that day? And why did she (Roberto knew the teacher had to be a mare) tell them about Special Cherry Day? If there was someone on the inside working for Cicchino, then they would've had to talk to the teacher to convince her to cut school early and to tell her students to go to Sugarcube Corner. If Roberto talked to the teacher and she confirmed that someone came to her and told her about Special Cherry Day, then that would confirm his suspiscion, especially if it was a human (the man on the inside could have hired a pony to do his dirty work for all Roberto knew). That was exactly what Roberto was waiting for standing in front of the Ponyville Schoolhouse.
After a few minutes, Roberto heard the school bell ringing, and soon after, a crowd of colts and fillies flooded out from the front doors. Roberto saw the Cutie Mark Crusaders as they walked out of the schoolhouse, and the three fillies noticed him too. They stared at the human with worried eyes, and Roberto stared back, but not one word was spoken between them, and soon after, the Crusaders decided not to linger around too long and went home. The mob boss waited a several more minutes until every foal has left the premises, and once the school was completely empty of any children, Roberto finally moved from his spot, put out his cigar on the fence (he didn't want to go through some pony coughing and telling him to put it out, he hated someone telling him to put out his cigar far more than just putting it out himself), and he walked into the schoolhouse.
The mob boss entered the classroom quietly, and on the other end, behind a desk, he saw a dark fuschia-colored mare with a cutie mark depicting three flowers with smiling faces getting ready to leave after a day of teaching. She didn't seem to notice the large human man in the room with her due to her being busy packing up her stuff.
"Good afta'noon," Roberto broke the silence by greeting the mare, who jerked up in surprise.
"Oh my goodness! You startled me, sir!" the mare exclaimed, her eyes wide and her forehoof rested on her chest.
"Sorry about that, miss. Didn' mean ta do that."
"So, uh, may I ask who you are, sir?"
The mob boss extended his arm. "Roberto Silano. An' ya are...?"
"Cheerilee. Nice to meet you," the teacher extended her hoof and shook Roberto's hand.
"Cheerilee, huh? Nice name," Roberto said, as he felt that her name was one of the less weird ones he's heard in Ponyville.
"I must say, it's quite a surprise, Mr. Silano. We don't usually see humans come around here, except for some of the ones I invited to teach the foals about Earth and human culture." That was the second time today Roberto heard those words upon entering two different schools, which he felt was a pretty funny coincidence.
"I'm jus' 'ere ta ask a few questions. I won't take up too much o' ya time."
"What about?" Cheerilee asked.
"About the day ya let ya students out early fa Special Cherry Day ova' at the bakery. Remember that?"
"Oh yes, I do. I heard a man choked there that day, caused quite a scene," Cheerilee said.
"News sure spreads," Roberto said to himself. "Well, I'm kinda curious about that. About why ya released ya students early and told 'em ta go ta the bakery."
"Really? Why?"
Roberto didn't feel like explaining his whole situation all over again, so he decided to just keep it short and get straight to the point. Also, Cheerilee was ready to go home for the day, so he didn't want to keep her there too long. "The three fillies who caused the whole incident said they were released early from school. I jus' wanna know what caused ya ta do that,"
"Well, I don't know why you want to find out about that. The whole thing just seemed like an accident. The early release was just part of our schedule for that day." Cheerilee then put a hoof on her chin and narrowed her eyes, as if remembering something. "Although, now that I think about it, there was something strange relating to the whole Special Cherry Day thing."
"And what's that?" Roberto asked, a glimmer of excitement forming in him.
"That morning, when I arrived here, I saw a human man standing outside on the side of the road, leaning against a tree and smoking a cigarette. As I was passing him, the man greeted me and asked about my job. We talked for a few minutes, and before I left he told me that there was a Special Cherry Day at Sugarcube Corner, and that maybe the foals would wann hear about that, since he thought they'd love it. So when school ended, I decided to tell my students about it, just for their fun on an early release day, and the Crusaders looked very excited about as they were the first to leave, and that's that.
"I didn't think about it at first, but now that I'm thinking about it, it seems very strange that a man like that was just standing in front of the schoolhouse, and it oddly feels like he was...waiting for me. I'm not sure," Cheerilee explained.
"Is that so? That is very strange indeed." A smirk creeped onto Roberto's face. On the outside, he was calm and quiet, but on the inside he was jumping with absolute cheer. His theory has been proven true.
"Can ya describe what the man looked like?" Roberto asked the schoolteacher.
"Well...he didn't look too different than you, I suppose. He had peach-colored skin, or white as you'd say..." Cheerilee and many other ponies had no idea why humans called the light peach-colored ones 'white' and called the dark brown ones 'black', none of them were even close to either colors, it never made any sense to Cheerilee. "He had a big nose, and he also wore a suit."
Roberto didn't find the mare's description very helpful. He was white? Had a big nose? Wore a suit? That essentially described most of his henchmen, except for the suit part, only a portion of his henchmen and their associates wore suits, but there was still too many for Roberto to properly narrow down his options.
"Is that it? Is there anythin' else ya can tell me about 'im? Any otha' notable features?"
"Uh, no, sorry. We didn't talk for too long, and we didn't even ask each other's names. And those were all the notable features I could remember," Cheerilee answered.
Cheerilee didn't want to say it out loud out of worry that she'd offend Roberto, but one of the other reasons she couldn't really say anything notable about the man's physical appearance was that Cheerilee often had a hard time telling a lot of humans apart. Unlike ponies that have a huge range of body colors, humans have very limited skin color, only ranging from dark brown, to light brown, to tan, to light peach, so it became hard to differentiate them from many other humans. It becames exponentially harder if the humans were in a crowd. If the human was someone she knew well, she'd probably be able to tell them apart easier, but if she was asked to describe any random human, her description would not help set them apart from other random humans.
Roberto simply nodded in response. "Hmm, alright then."
Roberto then got up from his chair and offered his hand to shake again, which Cheerilee took. "Well then, thank ya fa ya help, Miss Cheerilee. Ya've been really helpful."
"Um...well, you're welcome, Mr. Silano," Cheerilee said with a forced smile, though Roberto could tell she was still pretty confused by the whole thing.
"I'll be leavin' now. Ya 'ave a nice day," Roberto said as he walked towards the exit.
"Thanks, uh...you too," Cheerilee replied, a bit hesitant.
As Roberto walked away from the schoolhouse, he lit up a new cigar, and a smile creeped back onto the mob boss's face. His suspiscions were correct. If this wasn't confirmation the whole Cherry Incident was planned out, he didn't know what was. The man who planned out his hit thought he was so clever, but little did he know that Roberto was hot on his trail. But now it returned back to the matter of who actually arranged it. With a hit attempt this complex, it'd be quite a challenge to correctly pinpoint who the mastermind was, and there were too many of his own henchmen to choose from. But time will tell, he knew it would. Time will tell.
Suddenly, Roberto saw a figure running towards him down the road. The figure revealed itself to be a short fat man with tan skin and black greasy hair wearing a purple shirt and gold chain necklace, it was none other that Vincenzo De Luca.
Vincenzo was out of breath from all the running, which wasn't surprising since anyone could see he wasn't exactly a fit person. His shape really made him contrast with Gabriele, his taller thinner apprentice. When he arrived, he took a few seconds to catch his breath before speaking to Roberto.
"Ay, boss. Thank god I found ya," he said while panting.
"Vincenzo, what brings ya out 'ere? What is it?" Roberto asked.
"So ya remember all those scouts ya sent out to explore Equestria for potential resources an' business opportunities?"
"Yeah, of course. Why?"
"Well, one of our teams jus' came back with somethin', an' ya really gotta see it!"
Upon hearing that, Roberto's curiosity piqued. The mob boss then followed his caporegime back to the Silano House.