Disclaimer: I do not own any of the material appearing in this story. The OC's belong to their respective owners.

Moments After Bowser and Roman first met

"A little bit to the left-"

"Okay." A Shy Guy moved to the left, accidentally smacking a Hammer Bro with a 2X4.

"OW! MY left, ya dope!"

"Oh, I'm sorry."

The Shy Guy turned around as the Hammer Bro got clocked in the face with it again. "Yowch!"

Bowser sat in his destroyed throne, looking directly at Roman and Neo. "So let me get this straight. You think we have much in common."

"Yes." Cinder nodded.

"Alright. Then let me ask him a few questions. Are you of royalty?"

"No."

"Are you a tyrant?"

"Nope."

"Do you use fire?"

"I have Fire Dust inside of this cane."

"Do you kidnap?"

"That doesn't seem like my kind of thing."

Bowser frowned, looking at Cinder. "Woman, I have much more in common with you compared to him. You seem like the lady who'd be a tyrant."

Oh, you have no idea. Cinder thought with a smirk.

"Tell me about yourself." Bowser said.

"Ah, well, I am but a humble thief who steals hundreds, if not thousands of dust for… I'm not sure what this lady wants with it, but if she's that desperate, I can provide."

"I see… is that what you're going with?"

"I'm not going to reveal all my deep dark secrets to a big guy like you. Not yet." Roman chuckled.

Bowser turned to Neo. "And what about her?"

"She's mute. She tries to talk but it's painful for her." Roman explained. "And she used to have another name but that was the old her. Her name is now Neopolitan."

"BWAHAHAHAHAHAHAHA!" Bowser cackled.

"What's so funny?"

"You named yourself after an ice cream flavor! Have you ran out of ideas for names where that was the best you could think of?"

Neo frowned, folding her arms.

"Neopolitan… pah! Of all the names you could've come up with… well, at least you didn't name yourself Rocky Road or Moose Tracks. Bwahaha!"

Cinder chuckled. "I say these two could be valuable assets."

"Valuable! Good one." Bowser got up from his throne and walked toward the two, towering over them. "They don't look like they're worth anything."

Believe me, I plan on disposing them myself when they're done… Cinder thought. "Anyway, I figured they would help you defeat team RWBY and the Mario Bros."

"I can take care of them myself." Bowser walked off, shoving his shoulder over Roman. "If you want to help, that's fine by me. Just don't get in my way."

"Believe me, big guy. I'd rather not get in the way by someone like you." Roman said before sweatdropping. "Definitely rough around the edges."

"Ah, don't worry about him." Kamek approached. "He tends to be quite grumpy whenever he's beaten by Mario. Although there was a time where he didn't care all that much…"

"Really? What was this time?"

"Ah, I've said too much. Perhaps when he gets to know you better, he'll be more approachable." Kamek walked off. "Of course, that's a big maybe."

"I see." Roman nodded as he noticed Cinder walking away with Emerald and Mercury. "And where are you going?"

"Just running a few errands. We'll be back when the time is right~" Cinder giggled as she walked off with the duo.

"Yeah, well, don't be a stranger or whatever…" Roman mumbled.

["So… now what?"]

"I'd say… we get right to work and figure out a plan to stop Little Red and… well, Big Red."

Is that what we're calling Mario? Neo thought with a silent snicker.

Later…

Neo walked by Junior's clown car, noticing that he was working on it. She approached him as Junior turned around to the sound of her heels. "Ah, hi Nea… Neo… Neah pah…"

["You can just call me Neo~"] Neo smiled.

"Was that sign language? I'm just beginning to learn it." Junior said. "I believe you said… "You like to eat rocks"."

Neo silently giggled and shook her head. ["Not even close."]

"Bah… I'll never understand hand signs… can you write instead?"

Neo pulled out a notepad and began writing something down before handing it to Junior.

"I can, but it'll take too long… plus hand cramps suck."

"That's understandable." Junior nodded as he turned around. "I really wanna impress papa. I'm making my own Clown Car. I feel like I'm missing something though… I got sawblades, Mechakoopas, cannons, drills… what am I missing…"

Neo rubbed her chin and then an idea came to her as she punched the air to give him an idea.

"Boxing gloves? Ooooh, that's perfect! I can borrow some from one of the Sumo Bros… they barely even touch 'em."

Neo smiled, then looked at a spike pillar and pointed to it.

"You want me to add spikes to the boxing gloves?"

Neo nodded.

Junior sweatdropped. "Tempting, but I wanna pummel Mario, not kill him!"

Neo tilted her head. And yet, buzzsaws are fine?

With Roman and Bowser…

"So, what's the deal with you kidnapping Peach anyway? Is it because she's attractive?"

"It's complicated, but Mario and I have… a history with Peach, let's just go with that."

Roman rubbed his chin. "Ah, so you do like her! Have you ever attempted to flirt with her?"

"Yes, but it never works out."

"Ah, perhaps you ought to work on your approach. Like, for example…" He cleared his throat. "I guess… love really makes a guy come out of his shell". Raise your eyebrow and smile too. Give a little chuckle. That'll definitely woo her."

Bowser rubbed his chin in thought. "Gee, that sounds like a good idea-"

"See? You got i-"

"IF I HADN'T USED THAT LINE BEFORE!"

Roman sweatdropped. "Oh."

"It was still a great pick up line!" Kamek said nearby.

"Kamek, I keep telling you that it wasn't!" General Guy said.

"You're just jealous that I came up with it before you!"

"Am not!"

Roman snapped his fingers. "How about playing on the piano and telling her how much you love her?"

Bowser pointed to a smashed grand piano. "I think that blonde bombshell stepped on that."

"Ooooh…"

"Yo, Uncle Bowze!" A voice said as they turned to see the Koopalings approach him.

"We're back from vacatiooooon… woooow, this place is a dump." Wendy said. "What happened?"

"MY PIANO!" Ludwig yelled as he ran over toward it. "Oh, my poor precious baby… what happened?"

"You missed it. I actually kidnapped the Mario Bros-"

"Again? After that whole mess with the Vibe Scepter?" Lemmy asked.

"Vibe what?" Roman blinked.

"Yes, but this time I had kidnapped Peach. And then out of nowhere, these four teenagers come in and beat me in battle, and then adding insult to injury, they rescue the Bros and Prince-"

"You got bested by teenagers?" Roy folded his arms. "Wow, that's pathetic."

"One had a gun scythe, one had a rapier, one had with what I'm assuming is a ribbon gun and… the other looked like an MMA boxing gal."

Roy blinked. "That's… slightly less patheti- wait, did you say gun scythe?"

"Hardly seems practical…" Ludwig mumbled.

"MORTON WISHES TO SEE IT."

"BAHAHAHA! Now that's something you don't hear everyday!" Iggy cackled.

"By the way, who's this guy?" Lemmy asked.

"Ah, right. This is Roman Torchwick. He'll be working with us along with a short girl named Neopolitan. Yes. As in ice cream. Roman, these are my nephews and niece. Ludwig, Roy, Morton, Lemmy, Larry, Iggy and Wendy."

"Pleasure to meet you." Roman said.

"Whatever." Roy walked off.

"Nice to meet ya!" Larry greeted.

"So… what now?" Iggy asked.

"Lick our wounds and start planning our next scheme." Bowser said.

Sometime later, right when Hades started doing shenanigans…

"Where did all these things come from!" Roy demanded as the Underworld Army kept making a mess of things as the Koopa Troop proceeded to fight back.

"MORTON PUMMEL STRONG ARMED THING!" Morton yelled, going toe to toe with a Clubberskull while several Bob-ombs exploded near some Mimicuties. Bullet Bills were shot at several Fort Oinks.

Another Clubberskull tore through the castle, pummeling anything in its path as it soon came crashing into Junior's room. "SURPRIIIIISE!" Junior yelled as he fired cannonballs at the Clubberskull, only for said cannonballs to bounce off of him. "...Uh oh…" He whimpered as the Clubberskull roared and charged directly at the young Koopa.

However, a fireball struck the Clubberskull from behind. It slowly turned to see that it belonged to Roman, who had stuffed a Fire Flower inside his cane. "Step away from the kiddo, big guy."

The Clubberskull approached, swinging its fist to strike Roman but he ducked at the right moment as the Clubberskull smashed through a wall right as Roman slipped by, pulling out a Tanooki Leaf and absorbing it as the Clubberskull turned around and swung both arms down, but he turned into a statue as the Clubberskull struck him, but nothing happened as the Clubberskull pounded away.

Meanwhile, Neo slipped through and grabbed Junior's hand, the young prince eager to get out of there as Neo picked him up and put him over her shoulders in a piggyback and ran off, which caught the Clubberskull's attention as he chased after the two and leaving Roman behind.

The statue wore off as Roman turned around, pulling out an Ice Flower and shooting it from behind with his cane to slow it down, but it wasn't enough as the Clubberskull caught up to the two and swung its arms… only for Neo and Junior to shatter, confusing the monster as Neo and Junior hid inside a room, the former turning to the young prince and put a finger to her lips as he nodded.

"Looks like they outwitted you, big guy." Roman chuckled as the Clubberskull turned around and with a loud roar, it charged directly at him… only they heard a loud roar as Bowser dropped in and blocked a swing from the Clubberskull.

"Get out of my castle!" He snarled as he clutched hard and swung the Clubberskull around, sending it flying through several walls until it landed into a lava lake, where it instantly melted.

"Wow… that's some strength you got there. Those muscles just aren't for show."

Bowser turned to face Roman. "Where's my son?"

"Saved the little guy from big bad musclebrain. Neo took off with him while I distracted him."

"You saved my son?"

"Yes."

Bowser approached him and patted him on the back, giving him a proud smile. "You've earned my respect. You're not so bad after all."

Roman chuckled. "You're all bark and bite. I can respect that."

With a nod from Bowser, he turned around and got in a stance as more Underworld minions charged ahead. Bowser smirked, flashing his claws. "Think you can keep up?"

"Let's see how many I can take out compared to you." He said as the two shared a fist bump before charging ahead as Neo jumped in with them after Kamek threw a protective barrier around Junior.

Far, FAR into the present…

Roman sat down at a cafe in Solana Town, leaning against a chair as he drank his beverage with a chuckle. "To think it all started with us not getting along very well…"

He smiled, looking up at the sky, closing his eyes as a small breeze blew past him. "You're not just an ally, Bowser… to me, you're a brother in arms. Hell, I'm proud to even call you an actual brother. And I'll definitely drink to that."

So, this was one of the earlier Gaiden ideas when Gaiden was just in its infancy. I actually remembered this Gaiden idea a few days ago on the spot. I think Jacob came up with this one...

Ibuki: Aww... they really do have a strong bond.

Deadpool: A brotherly connection!