Chapter 7
Present day
"Good afternoon Astrid. I had a lovely time on our date yesterday." Hiccup typed as he said it out loud. "Would you be willing to join me at this lovely Bistro I discovered a few weeks ago?"
"How does that sound? Not too clingy?" Hiccup asked as he looked around his office, which was filled with several men.
"I think it sounds fine," A bald man spoke up.
"Everything sounds fine to you Ryker," Another spoke up.
"Shut up Viggo!" Ryker shot back.
"Hiccup did you seriously call us here to get our opinion on your love life? Or lack thereof?" Snotlout uttered as he lounged on one of the wingback chairs.
"What lack thereof? The boss got a date, didn't he?" A portly blonde uttered.
"He got a date, though I stand by my opinion! That pickup line should not have worked." Snotlout retorted.
"Oh come off it Snot. Fishlegs is right," A lanky blonde grumbled. "You're just jealous that the boss got a date and you didn't. You score when you follow Tuffnut's rules for dating,"
"Didn't your last date try to shove her heel up your…"
"Okay okay, moving on…" Hiccup interjected. "As much as my relationship status excites you guys. There is a reason I called you here. Grimmel's Gang." The mood in the room shifted into a more serious tone nearly immediately. "One of our warehouses got hit this morning."
"What's the damage?" Snotlout asked. "And do I finally get to sue someone?"
"Cool your jets, Phoenix Wright," Fishlegs stated. "Unfortunately, we have nothing to tie it to Grimmel… officially,"
"The fire burned down more than half the warehouse. Luckily the fire department responded swiftly." Fishlegs explained. "Preliminary report by the Fire Marshal states that it was caused by faulty electrical wiring."
"Screw faulty wiring. We both know what this is," Viggo growled. "Grimmel is getting back at us because we took over the East side shipping routes. Fires are Grimmel's thing. We know he has the marshals in his pocket."
"We are not going to retaliate," Hiccup announced much to the dismay of everyone in the room.
"Why not?!" Tuffnut uttered. "Grimmel is asking for it! My sis and I can totally take care of him,"
"And that's exactly what he wants. Retaliation," Hiccup pounded his fist on the desk. "Think about it, our position is still shaky at best. Up east the Hooligans rule. Sure we've been establishing ourselves in this city for the past three years, forging alliances, dissolving gangs, taking territory and trade routes but Grimmel's gang had been operating in this city far longer. He loved the chaos his gangs caused. We're seen as a thorn in his side because we value order. What do you think will happen when we retaliate when there is no clear proof?" Hiccup stressed. "The smaller gangs we've absorbed might rebel because it will show them that we can do whatever we want to others without proof."
"But doing nothing will just give Grimmel more power too," Snotlout stated. "We can't become his doormat."
"Who says we're doing nothing?" Hiccup raised his brow. "In about an hour, several of Grimmel's massage parlors will be getting a visit from SWAT, the FBI, and DEA,"
"Wait, I'm confused. I thought we weren't retaliating,"
"We aren't," Hiccup smirked. "There is absolutely nothing linking us to the several anonymous tips suggesting human trafficking at Grimmel's establishments,"
"Ooooh sneaky sneaky boss," Tuffnut laughed.
"You lot know how I hate human trafficking," Hiccup growled. "No self-respecting man would stoop so low as to use people in desperate situations for his gain."
"What about Alvin's crew?" Fishlegs asked. "They're still on the fence about allying with us,"
"Alvin's not a big threat. He won't bite unless we put one of his own in serious jeopardy. If the Outcasts want to stay neutral they can." Hiccup stated. "Alvin's smart. He knows that joining Grimmel will be a bad decision if he wants to deal with me,"
"What's his beef anyways? I know he and Uncle Stoick go way back but still,"
"That's not important right now. The Family is sending us some more muscle to strengthen our position. I want to take the city once and for all but we need a solid base or this will just end up in a bloodbath between us and Grimmel." Hiccup stated. "We're nearing the four-year mark guys. "This is what we've been working for,"
"Right on," Tuffnut cheered. "Our Hiccup's taking his place with the big boys!"
Right then and there Hiccup's phone dinged. He unlocked it and read the text. "There is something I need to talk to you about. I prefer it to be private."
"Oh…" Hiccup said as he reread Astrid's text just to be sure.
"What's wrong?" Fishlegs asked as he peered over.
"Astrid wants to talk,"
"Well that isn't too bad," Snotlout mumbled.
"Unless she found out that Hiccup's the soon-to-be boss of the largest Mafia empire on the East Coast." Tuffnut casually said.
"They went on one date. How could she even figure that out?!" Snotlout shot back.
"Well Fishlegs looked into her and said she was neighbours with this cop," Tuffnut retorted.
"Wait, hold on. Fishlegs, you ran a background check on my date?!" Hiccup questioned with a raised brow.
"What was I supposed to do?! The last three dates you went on ended in disaster!" Fishlegs exclaimed.
"They did not!" Hiccup uttered.
"The golddigger,"
"I was not that gullible!" Hiccup muttered.
"The conwoman,"
"To be fair… she had a good con going," Hiccup defended.
"THE ASSASIN!"
"She was hot!" Hiccup shouted.
"And a pain to dispose of," Tuffnut grumbled.
"Just text her back and say you'll meet at a neutral location," Snotlout muttered. "A public one. If things go south she wouldn't want a public spectacle."
"Right," Hiccup said as he texted. "Guys, what will I do if she dumps me for this?"
"Hey, it's not on you." Snotlout just shrugged.
"But she was so open about her situation at dinner." Hiccup sighed. "I wanted to tell her but seriously… when is the right time to blurt out 'Oh, I'm the soon-to-be head of the largest mafia outfit this side of the East Coast. Where would you like to go on our second date?'" He deadpanned.
Three years and two months ago
Henry stood in front of an imposing set of double doors. Beautifully crafted mahogany, likely from the Regency period as with the rest of the Mansion. He took a breath and knocked.
"Enter," came the commanding voice from the other side.
"You wanted to see me, Dad?" He shuffled into the office to see Gobber and Spitelout already there.
"Yes, Henry. It's come to my attention that your first meeting with the Family went very well." A man, big and muscled with a beard the shade of an orangy tomato, dressed impeccably in a pinstriped suit uttered.
"Oh come off it Stoick. If by going well you mean that the boy getting the hiccups three minutes into his speech showed them what type of leader they'd be getting then by Thor it went extremely well." Spitlout groused. "For Loki's sake, they are calling him Henry the Hiccup now!"
"At least he finished his speech," Gobber muttered. "That gotta account for something. Also, Hiccup isn't a bad nickname. It could be worse. Remember two-toed Louie?" To this, Spitelout glared at the other.
"Not helping Gobber," Henry… or well, Hiccup as he'd been so aptly nicknamed deadpanned.
"Hiccup you're 18 already. I want you to take over the family business in a couple of years and you've been involved in a lot of the grunt work growing up, however…" Stoick frowned.
"However…" Hiccup didn't like the 'however'.
"Some of the other heads expressed concern you'd be up for the task," His father finished.
"And rightly so. What's he gonna do? Hiccup his enemy to death?" Spitelout muttered.
"I was nervous!" Hiccup retorted. "Do you know how nerve-wracking it was to have the eyes of Grandpa and every head of every major outfit and their wives on the East Coast on you?"
"Be that as it may I've proposed something to placate them," Stoick responded.
"I'm not going to like this am I?" Hiccup groaned.
"Berk is an up-and-coming metropolis." Stoick continued. "We've thinking of expanding and you're going to get us a foothold in the city."
"Excuse me, I'm going to what?" He uttered.
"You'll get the Hooligans a foothold in the city within four years," Stoick stated. "The other Heads have agreed to accept you as my official heir upon achieving this. Naturally, it will be your own outfit, just like how all the other heads are operating. You can run it however you like. Deal with what product you like and bring the Family profits. In four years when you're successful, you get a seat at the table with voting rights."
"I'll have the same rights and responsibilities as any other Head, right?" Hiccup questioned as he knew of some of the perks he could cash in on.
"Yes, but you gotta start from scratch like we all did." His father stated.
"Okay, I'll do it. On one condition." Hiccup said.
"Which is?"
"I get to pick my team,"