This right here is best read immediately before or after watching RWBY: Episode 1 - Ruby Rose, if only for a refresher on the events of the episode described here. This little side-story is intended to seem as if it could very well have happened (aside from obviously not being Canon. I own nothing. Hilarious to even think.) by fitting in between episodes and events.

Red Devil

Doug did not have the makings of a good henchman. He was sure of this, because he knew the four merits a good henchman had to have;

Rule 1: A good henchman looked generic, and he fit that bill perfectly. He had been sent along with four other cronies, all of them wearing matching attire of black suits with fedoras, crimson ties and shades accentuating the look. They all had differing facial hair, though what he had was more like stubble his actual hair was a bit longer than theirs, poking out the sides of his hat dyed black as well. He might have been lagging behind the group a bit but that hardly warranted their concern.

Rule 2: A good henchman was cost efficient. If they had been considered elite henchmen, they would be getting paid a far better wage for following this Torchwick fellow; but as they were not nearly talented enough to boast a title like elite they were all little bang for little buck. It wasn't as if a store robbery needed an awful lot of skill, so again, he and his co-workers were a perfect fit.

Rule 3: A good henchman listened well. The order must be followed, if necessary repeated only once. He could do that fine, but put himself above what may be asked of him. The others here might have been of the same mind as he was, but were likely too stupid to understand when there was a line they shouldn't cross. When you were one of many, the numbers did that to people.

Rule 4: A good henchman, lastly, saw things through no matter how bad they got. Your goon should stick by and follow your every whim straight to hell itself for whatever meager sum you were supplying them with for their efforts. While many henchmen would sometimes bail out on their employers when the situation gets beyond saving, he was easily the first to dip out of service the moment a job went south.

As these second two of four traits were failings he wouldn't appropriate, Doug would never make a good henchman, or so he figured. Being a good henchman wasn't necessarily needed to succeed as a henchman, however, if his current status among the band he followed was any example. Technically, his tendency toward self-preservation had helped Junior more often than it hindered him; Doug unfailingly came back to tell his initial boss what went wrong, and what to expect most nights if a gig went awry. This was shaping up to be a night unlike those, where the lack of action was making them practically fall asleep at Torchwick's heels. Finally, after long hours of walking through the streets and shooing away scared passersby, they discovered a Dust Shop open this late in the night; From Dust Til Dawn. Tacky name, but it got the point across.

They stepped into the store with a jangle of chimes, and it was quiet for a moment until Raymond started talking. One of his fellows pulled a gun on the clerk hardly halfway through their boss' sentence, eager to get this over with. "Do you have any idea how hard it is to find a Dust Shop open this late?"

"Please, just take my Lien and leave!" The older man rasped with his hands skyward.

"Sh, sh, sh, sh... Calm down, we're not here for your money... grab the Dust." With that, the Henchman's third rule; obey. Four of them grabbed canisters and started filling with the dispensers at the side; one revealed a case and began demanding solid crystals. Doug glanced back from his corner grabbing some frost Dust, hearing another of his fellows speaking with a customer they must have missed; the kid by the magazines must have been twelve or something from the size, and she was wearing what may as well have been a gothic Lolita version of their own outfits. It was actually a little uncanny.

"Alright kid, hands where I can see 'em!"

All Doug said about the situation was more of a whisper to himself; "Is her cape moving by itself? Is anybody else seeing this? I mean what the fu -"

"Hey, I said hands in the air! You got a deathwish or somethin'?" Sliding back her hood, it became apparent that she was wearing headphones that must have made her oblivious to the whole event taken place so far. Doug turned back to his work, guessing the kid would soon be joining the owner reaching for the ceiling.

There was some more idle chat between them both, sounding like even more reiteration on just what was happening, and then the sound of hard impact and some crashing. Doug turned around fast enough to see one of the other cohorts hold her at gunpoint, shouting; "Freeze!"

Half a second later, he was soaring out the window on the end of her feet. She rose from the street as they all gawked at her out the shattered window, as something in her hands soon unfolded with the sounds of sliding metal into a scythe bigger than she was. Doug backed up involuntarily.

"Okay... Well? Get her." Torchwick commanded, and they served to define the Henchman's fourth rule, running out to greet the little hellion.

"Yeah, no..." Doug chose to watch from the window seat. Torchwick, who had migrated to the door, had yet to notice or didn't care. Within just a few more seconds, the girl had done some crazy spinning dropkick, along with wild swings of the back of her scythe powered by gunshots integrated with the weapon that hammered the others either across the street or down into craters. This suggested he had picked the right option.

Around this point, Doug looked back at the Dust Shop owner, silently made an apologetic gesture, and promptly made for the back door. He heard Torchwick make a witty comment about the Henchman's second rule, one that Doug was proving him right about in a different sense. There was an explosion on the other side of the building, and upon exiting the alleyway to escape saw Torchwick climbing a ladder up to the rooftops, now past the miniature she-beast. How had he gotten over there so fast?

It didn't really matter, as he knew that was the way to the getaway airship –and he should likely be making his way there too... that was until the tiny red devil herself rocketed up after Torchwick. He would have to round the building, as the aircraft was surely lowered to ground level right now. Doug sprinted around the block into the blind spot where fortunately, Torchwick's own boss had parked and gone silent. He climbed into the side of the ship, and she hardly gave him a glance before ignition, which he wasn't ready for and nearly fell out of the ship because of. He made a sound that could have been a curse or a cough from impact with the back wall.

They rose up to a height where Torchwick walked dramatically off of the roof into the hold, tuning around to look at his pursuer. "End of the line, Red!" with this, he hurled a Dust crystal he had hung onto at her feet, firing a projectile from his cane at the rock to detonate the potent crystal. There was yet another exciting explosion, and Torchwick laughed about the quick victory until the smoke from the blast cleared.

Some blonde chick was standing there, purple sigil floating in the air like a shield. They were unscathed... and this other cape-wearing broad proceeded to bombard their ship with purple orbs of light that made the thing wildly twitch in the air. Torchwick kept his footing; Doug fell on his face and slid to the front end of the ship. He grunted though he couldn't hear it over the systems beeping manically when Torchwick stepped on his back followed by his head to enter the cockpit, grinding his foot into Doug's cranium –intentionally, Doug would bet –as he informed the red-dressed pilot that they had a huntress on them. Wasn't this just perfect.

Torchwick backed off so that this lady's glass heels could stab him most painfully on her way overhead, and the Redhead allowing her to pass made one last step onto Doug's head again to reach the pilot's seat. Doug managed to rise and stumble into a sitting position against the wall behind the front seats, just out of view from the windshield. There was a sound he couldn't really describe, followed by rolling thunder and the sound of air displacement as footlong icicles began to rain on the aircraft, sliding them down on an angle. Torchwick was almost hit in the face by one, which in turn impaled the seat when he moved and stopped near Doug's eye. He found himself rolling to the side, though his reflexes wouldn't have saved him if the chair hadn't stopped the deadly raindrop in the first place.

There were some high-pitched combat clashes ringing through the air repeatedly now as some kind of otherworldly battle took place. Doug tumbled out next to Cinder for a moment, around the time the blonde on the roof decided to form a giant floating spear out of broken rooftop. As she launched it toward the ship, the woman in the red dress next to him braced against the door slid aside when Torchwick pulled off a strong tilt to the left; making the lance of stones deflect off the armor on top... which in turn dumped Doug out of the aircraft with a shout and a few swears muffled by the scraping of the attack against steel, hurtling into a window that surprisingly didn't break. He bounced off of this and half-caught a hold of a street light, which he soon smacked against and lost his grip on to descend backfirst into the sidewalk.

He stared up more out of a lack of ability to move in so much pain, watching as some heat waves and ashes came off the battle raging above. There were a few gunshots too. He really didn't care anymore. He rested for a few moments more on the pavement, but this proved to be too long.

"Hey there buddy. Need a hand? We certainly did, a few minutes ago." One of the other cronies was looking down at him. The other three soon occupied the other sides.

"Just when you think that Doubtful Doug can be trusted after all, huh?" the one with the goatee said. They knew him pretty well by now, but these guys were all the same to Doug. He could probably recognize them better by what little they had different than by actual name.

That said, Beardo laughed a bit. "We don't have much time, guys. The cops are sure to be making tracks."

"Can I just say one thi –" Doug was cut off by the flurry of blows from all sides, and after a minute or two of leaving him bloody and bruised they hoofed it at the sound of sirens. Briefly, he caught a glimpse of the Blonde Witch and the Red Devil leaving the premises, rolling pitifully into the shadows in hopes of not being seen.

If any of these things served an example, Doug was not a good Henchman, and likely never would be.