Author's Note

Written because I had some free time between working the past week or so and thought I'd fill it with something half-productive. I suck at writing, so apologies in advance.
If people don't think it's completely terrible, I guess I'll continue with it.

Minor setback

A few years earlier:

Damn, she's coming back, the stallion thought as alarm bells began sounding in his head. All too aware of the dangers of losing his calm, he mentally shook himself and began contemplating. Come on, dumbass. You ain't gonna get nothing done by panicking.

He took a deep breath.

His mark had made an unexpected move by returning to her post earlier than he'd predicted. He was operating within his home town this time: everypony trusted him and would therefore never present any obstacle to him in that regard, but if he did ever get caught it would have serious, irreparable consequences. Here, he found himself possibly looking at just that.

You're good, just keep it together and think calmly, the voice in his head told him. He observed his surroundings, pondering his situation as he did so. Now, there wouldn't have been a problem if she'd afforded him only a minute or so longer like he'd presumed she would (she was normally kinda slow whenever he came to collect deliveries), but as it was he'd had to sift through the drawers under her desk to find his prize, removing whatever was in his way in the process and if she'd walked in on him now, she'd have probably guessed what he was up to right away.

Then, the stallion noticed the clutter on the mailmare's counter. He'd timed his move well, it seemed; Ditzy Doo was usually busy this time in the morning, so it made sense that general tidiness wasn't that high on her list of priorities at this particular moment. Indeed, between Rarity's various deliveries which had to be collected from the depot and well, whoever else frequents the mailmare he supposed, Ditzy hadn't even had chance to finish her breakfast; a muffin, naturally.

Pocketing the bag of stolen bits hurriedly, he managed to place one of the apples in his saddlebags on the floor while the mare was still just out of sight. She was just emerging from the back room as he feigned tripping over the apple: at his size, even the half-hearted tumble he took sent everything on the counter that could move flying and all over the floor. He kept up his act, widening his eyes and lifting himself from the floor. He took the opportunity to observe the damage done, a fake look of apology plastered on his face as he looked between it and the mare. It was good enough he supposed, enough of a mess to distract from the missing bits. Between that and the presumption of his innocence she would no doubt have, she'd probably be more upset at him over her now-ruined muffin.

''Mighty sorry, Miss,'' he lamented, placing the apple back in his bag and picking up some of the various envelopes and packaging on the floor. A brief look of despair took her face- her day was busy enough without his contribution, he supposed- but she shook her head and quickly snapped out of it.

''It's alright, don't worry. Wow, I thought I was clumsy,'' she joked. ''You should be more careful Big Mac, you could've hurt yourself,'' she said more seriously, joining his effort to remove the mess. A brief feeling of guilt shot through Mac's conscience at this. Thankfully, it was something he'd long ago learned to deal with. ''All thanks to me berating you; you're welcome buddy''.

''Ah'm a little tired today, sorry,'' he lied.

She smiled at him. ''Yeah, I can see that. I'd be tired if I worked your farm all day. You should take a break more often''.

''Eeyup,'' he responded in his usual manner.

Ditzy then remembered why he was there. ''Oh, yeah- here's your package from Appleoosa. This time I found it near the front,'' she grinned sheepishly. ''She should really start arranging those things by date order. Or alphabetical. Whatever''.

''Eeyup,'' he repeated himself as she handed the object to him.

''So, how are your family? I hope you're getting along alright after what happened to Granny. I know it's tough to lose somepony close to you,'' she began, ''you should come by and talk more often, you know- it might help-''

''Real grateful for that Miss, maybe I'll come by when I got time,'' he took the opportunity to cut the discussion short. Granny Smith's passing just under a year earlier was still rather a touchy subject and he preferred to drown out such troubles with his work than weep about it to ponies. Besides, he had the rest of his family to talk about that with. Pragmatically speaking, he was also becoming more and more aware of how important it was to vacate the area once one had committed a crime.

She wore a slight look of disappointment at this dismissal, but brightened up quickly enough. ''Oh, okay then. No problem. See you again soon!''

On this occasion, he'd worn his saddlebags only to provide a ruse, just in case collecting the delivery hadn't done the trick. Nopony would have questioned it, he'd figured; with their recent decline in business, there was by now going to be some expectation of him to simply give up trying to sell anything every now and then. As it happened, he did have one or two things to reflect upon and he didn't feel all that up to visiting the market today.

The walk home between Ponyville and Sweet Apple Acres always brought him by the local tavern. Resisting the urge to do a little thinkin' drinkin' was sometimes hard when he felt guilty or conflicted and had some free time; today was one such occasion. Thieves typically were supposed to spend their goods on just such debauchery, after all (though a brothel would have been a bit more appropriate in that regard).

This was countered by several things of course: one it was stupid, two he was better than that and Ponyville folk were expected to know their limit, three he was sure AppleJack would have one or two words to say about it (''I think: 'Big McIntosh, whut in EQUESTRIA were you thinkin'?' would be a good guess,'' his inner self chuckled), four it wasn't even noon yet and most importantly of course, he needed every bit he had to pay back Filthy Rich.

For an apparent 'friend of the family', Rich had proved himself quite the miser when Granny had passed away. As the eldest sibling, Big Mac had found himself in charge of more than he was used to. Decent and dependable as she was, his younger sister AppleJack (and youngest sister Apple Bloom had tried, too) naturally stepped in and helped with much of this responsibility; he was sure he'd never have managed without her, in fact.

One issue he hadn't the heart to reveal to her though was the debt Granny had left them in. He didn't know whether it was a sense of fear for the old mare or a genuine sense of respect for her that had kept Filthy from pursuing it while she was alive, but in addition to the business done between the Apple and Rich families, Mac discovered a- presumed forgotten- debt of one thousand bits the Apples had to borrow from Stinkin' Rich, one year decades back when an unusually grave case of Apple Blight caused the Apples' harvest to utterly fail. Apparently, the debt had been put off so long Granny had mistakenly presumed that the whole thing had been dropped out of sheer good will.

''You wanna assume the best in ponies you know well''. He looked up into the sky in a moment of reflection. ''Sucks real bad when life don't work out that way''.

Unfortunately, the current head of the Rich household had no such reservations with Big McIntosh and now expected interest in addition. Seeing it as his duty and a test of his worth as a stallion, Big Mac had- perhaps foolishly- taken it upon himself to defend his family from this reality. It had gotten to the point where he felt it would tear his family apart to learn of their predicament now, which would really have been a shame since they were still finding it hard to live with the loss of their Grand-Mare and with all the time AppleJack would have to take from her duties as one of Equestria's most important figures; he'd never get over the shame of it. So, the task fell to him.

Now, as he approached the entrance to his farm, he couldn't help but wonder what might have been if he'd just followed his sister's example and been honest from the start. He knew better than to keep such secrets from his family and it was pretty clear now that he'd acted irrationally. Now here he was, stealing from ponies he grew up around to help make reparations. Still, it was too late now and there was no point feeling sorry for himself- he was better than that, at least.

''Coulda been worse after all. Least you ain't a rent colt''. Stop trying to be funny.

His chores would probably help take his mind off things.

Quietly (except for a brief moment Winona, the family dog had come to greet him), he made his way to their barn, an impressive structure into which years of proud labor had been dedicated. It spoke volumes to the sense of quality Mac (like all his family throughout the generations) possessed: painted bold red and in immaculate condition, it provided housing not only for their livestock but also acted as a form of storage for tools and equipment and the like. As Mac entered the barn, a relatively new enclosure within also revealed itself- located near the more heavy-duty equipment, Mac figured when he had planned its construction that nopony other than himself would find reason to look into that area.

He opened it to reveal stashes of his prizes over the years: apart from the gold he had still to pay Filthy, there were some more sentimental prizes Mac couldn't bring himself to sell off, each with their own story: a diamond- encrusted necklace, for example, taken from the residence of some well-to-do mare in Manehattan, years ago when he was only young and visiting his Aunt and Uncle Orange; back when he first discovered he had a talent for skulduggery- promptly having vowed never to engage in such behaviour again when he saw how much it hurt other ponies.

''Well, it's good of you to realize you're hurtin' folk and that's bad. Give yourself a nice pat on the back, champ,'' he told himself sarcastically. Valid point, but he couldn't help but be fond of how well he'd pulled off that particular stunt. Credit where it was due, after all.

Manehattan families unfortunately tended not to be all that stable compared to in more traditionalist towns and this particular mare- a friend of his aunt and uncle- recently discovered her husband had been unfaithful, leading to dispute.

Having been dared to steal the necklace by some of the other colts from Manehattan, the young McIntosh naturally felt pressured to do so and being far more capable of cunning than one would have expected, picked up on this situation and took advantage of it by misinforming the couple's daughter (who he got landed with on occasion) he'd witnessed her father with another mare while he and Granny Smith were visiting Bridleway.

''But Mommy said Daddy wasn't allowed to cheat anymore!''- the filly was only little, the way she'd phrased it seemed amusing at the time. Not so much in hindsight.

As he'd predicted, she immediately relayed this to her mother, whose bad temper- coupled with the fact that her father had been drinking excessively that night, set off quite a dispute.

''Now you're calling our daughter a liar?! I can see now you have no respect for this family!''
''Yeah, 'cause you're a stupid bitch! You think I really wanted foals with you? Dumb broad''.

Even then, he thought perhaps it had gone a step too far. Hopefully the frightened filly watching got some decent counselling afterwards. ''Reckon she was fine,'' he reassured himself. ''She'll just hate her parents her whole life or think every stallion's a scumbag, you didn't mess her up at all''. Geez.

The chaos caused provided perfect cover for Mac, who simply had to pick the necklace off the floor when the dust had settled, after the stallion had broken several pieces of furniture in his stupor.

The young colt was certainly pleased with himself- he didn't even think it would go that well! He had expected the couple to simply walk away as their daughter watched and then for her mother to simply assume her husband had taken her necklace out of spite. The awe and admiration he got as he presented his prize to the other colts, the feeling of self- worth, he loved it.

Learning the incident had caused the couple to undergo a rather nasty divorce some weeks later wasn't all that fun, though. Yep, somehow he doubted that poor filly would enjoy her childhood very much.

Mac decided he'd digressed into his memories enough and brought himself back to the present. Stashing his bits and his saddlebags away in the closet, he closed the door and prepared himself for the rest of day's work. At least, he'd planned to until he heard a knock on the barn door.

''Hello?'' he responded, confused as to why any visitor would go to the barn instead of the farmhouse.

An amber earth stallion with a slick, dark-grey mane entered the barn; clearly a businesspony by all outward appearances. His cutie mark of three sacks of money suited him thus.

Of course, Mac thought irritably, it was somepony looking specifically for him.

''Well, Good Mornin' Mcintosh! I hope you're havin' yourself a good day so far?'' he smiled, almost innocently.

Big Mac wore a neutral expression and with a simple ''Eeyup'', made to fetch the bits Filthy Rich had no doubt come for. ''At least he came to you. Saved you the trouble, didn't he?''

The smaller of the two stallions took his dues gratefully and kept them there in his hoof, looking a few times between the sack of bits and his associate. Sensing Rich was about to waste his time further instead of leaving as was usual at this point, Mac interjected pre-emptively: ''Mister Rich, I'm real sorry but you know I ain't got time to talk. I'll have the next payment soon enough, don't worry none''.

Rich gave his usual slick smile. ''Come now, Mac. I really don't think I deserve all this cold treatment you give me now. Do you honestly think it ain't reasonable for a pony to ask for what's owed him?''

Eh, he had a point Mac guessed. Bit of a dick move in terms of timing, but sure it wasn't as if Rich had no right to his money. It mattered little to the red stallion at this moment in time. He shrugged. ''Ain't no cold treatment, sir. I got chores to do, see''.

Filthy's smile grew menacing. ''A stallion of your talents still humble enough to do chores all day? I'm mighty impressed, sir''.

That got Mac's attention. ''Scuse me?''
''Your sisters ain't here, are they?''
''Dunno, probably not''.

Rich's tone grew more serious. ''I'll cut to the chase, Mac. I was surprised enough to learn you'd tried to settle our debt yourself. Now you're stealing from ponies? I'm intrigued''.

When faced with a sudden, unexpected threat, Mac had learned to appear calm and unafraid; self-discipline came naturally to him. As soon as that last part exited the businesspony's mouth, however, he had to admit his adrenaline spiked. There was no subtle way about this. Filthy Rich surely suspected Mac's intent, but his proximity and the Apple stallion's clearly superior physical abilities meant Mac wouldn't have much trouble dealing with him before he could escape and the dirt on the ground was Rich's only potential weapon, which Mac knew well enough how to prevent. He knew he'd be on the run for the rest of his life, but right now he saw no other option.

Seeing the red stallion's hoof make a movement downwards, Rich backed off and loudly objected: ''Hear me out, Mac!''

Mac had already drawn his knife and was more than prepared to end his adversary; though by no means an experienced killer, his skills were more than enough to deal with the pony in front of him.

''For Luna's sake, calm down! What're you gonna do? Just kill him like that? Let alone the fact everypony would notice him missing right away-'' Alright, alright!

He supposed there was no additional risk to be had from at least hearing the stallion make his case. Mac nodded for him to continue, making sure Rich knew he wasn't letting down his guard.

''I just got back from the mail depot. It was innocent enough, I swear. Pickin' up a gift from a friend of ours''. He presented a small box as proof of this.

Not quite in the mood for a story, Mac felt his patience wear thin and he towered over, staring into the azure eyes with his own brilliant green ones. ''That don't concern me. What reason do I have to let you live? Speak quick, now!''

Rich scowled back at his aggressor (though part of his mind was indeed terrified). ''Well, the fact that you wouldn't last a week before the guard got you- let's think about that now''.

Mac brought his hoof down on the pony's front leg and Rich fell to the ground. ''I'm well aware. That doesn't help you''.

Filthy Rich gritted his teeth from the pain, but recovered quickly enough and looked up to his assailant. He paused and then grinned. ''I'll ignore that little transgression.

''Okay, so you know where I was going. Ms. Ditzy started goin' on about how she'd lost some money. I wasn't too interested at first but then she mentioned you and your little 'incident'. Sounded familiar. I remembered back a couple months ago: Rainbow Dash and some fella from the Wonderbolts came over to buy from your farm and she accidentally got served alcoholic cider instead of regular cider? Of course, everypony knows she can't handle a drink well. She cries all over town about how she lost her jacket. Almost got kicked out of the 'Bolts for that, I hear. Then the jacket turns up on the black market in Fillydelphia; official Wonderbolts merchandise, worth hundreds''.

''You think I got all day, do you?''

Rich sighed. ''Fine. If you promise never to raise a hoof against me again, I think maybe I got a way you could reduce your debts''.

''Blackmail? I think you're getting a little too brave now''.

''Nothing of the sort, my friend! Think of it as a deal. A way to ease our families' relationship, just like how it used to be. You prove yourself, maybe I'll even start paying you for it. Whaddaya say?''

''I don't believe you,'' growled Mac.

Filthy made to reach into his shirt pocket. Mac responded by flipping the knife grip and drawing back to strike downwards. He relaxed a little, however, when all Rich pulled out was a folded piece of parchment. Content there was no trick here, Mac took it from him and opened it, glancing between it and his subject.

''This is to confess that I, Filthy Rotten Rich, proprietor of Rich's Barnyard Bargains, Ponyville, am complicit in whatever illegal activity McIntosh of the Apple family, has henceforth decided to engage in, having solicited his involvement in said acitivity''. It was followed by his signature and looked convincing enough. Mac was still unsure.

''He wrote up his confession for your crimes, signed and dated it? This is just weird dude''. Yeah, but he found it convincing enough and practically speaking it would work. Paying off his debt was a pretty good incentive too. ''Uh-huh, the same way a fish has a 'good incentive' to take the bait from a hook''.

That was true, Rich certainly wasn't somepony Mac would deem trustworthy and this did come off as unusual. Then again, what better way to ask for Mac's trust did Rich have? It kinda made sense it that regard. Mac was not at much liberty in terms of choice either, he was the one who'd been discovered as a criminal, he was the one who owed the debt and now that he was thinking more clearly, killing his associate wasn't really a solution given he'd face legal consequences either way.

''Making a mistake, dude,'' the opposing side of his mind shook its figurative head. ''Keep what's left of your decency. You cross this threshold, you might not ever go back. You heard enough about how the 'Underworld' tends to work''. If he refused and kept trying to pay this debt off, it wouldn't exactly be a good alternative though.

The stallion's more distant and hesitant behaviour was noticed and Rich interjected: ''You okay, boy? You're awful quiet right now''. Mac returned to the situation at hand.

''Thinkin'. Not something I expected... so, now I have leverage and I should trust you. That what you're saying?'' questioned Mac, allowing his subject back to his feet.

Rich turned to face his opponent. ''Indeed. Think what you want of me Mac, but I ain't stupid and I know you ain't either. It might take a while for us to earn each other's full trust,'' he conceded somewhat sternly, ''but now we got dirt on each other and we both got something the other wants. Surely that's enough to get us started here?'' he slowly held out his hoof. Although he put away his knife, Mac was hesitant to shake on the offer.

''What you got planned?'' Mac inquired, holding up his hoof.

Rich frowned at this but soon softened back up again. He began walking around the barn slowly, looking about and pondering. After a brief pause, he turned. ''Alright, well... since we're sortin' through the details, you tell me something first. You ever actually killed anypony before, Mac? Till now, I'd never have suspected you had it in you''.

Mac hesitated. ''Twice,'' he grimaced, not wanting to remember.

Rich seemed rather amused. ''You really that disgusted by it? Now, I've never been involved in that kinda business- really, I haven't- but I recognize a natural when I see one. Now, I know you're gonna say it were just an act, you were tryin' to scare me, but I've met one or two rough sorts before and- ''.

''Where's this goin'?'' interrupted Mac impatiently.

''These two ponies you killed. What brought you to do it?''

''Fight that got out of control and an escape that didn't go how I meant it to''.

''Interesting,'' answered Rich, as if he were just musing over regular business . ''See, I need to know you got the right composure for the job. I ain't sure about somepony who kills cause they lost control. You're not the squeamish sort, are you?''

''Nope. Hang on though, you hiring me for a hit?''

Mac found the idea off-putting, he did have to admit. He was sure he could become accustomed to the personal ramifications of the act if needed, but assassination tended to be a risky business, solicited often by the most treacherous of ponies who would quite happily set the killer they'd hire up to take the fall, thereby avoiding both the consequences and having to pay out- Mac certainly could picture Filthy Rich as the sort. Not to mention it left a far greater impression on those involved than anything he'd done in the past and Mac did not like drawing attention where he could avoid it.

''No, no. Nothing like that. This first job's more of a bit of sabotage, a rival business of mine in Manehattan. They're still small but I reckon they'll grow.'' the pony explained. ''Thing is, maybe you'll find you have to kill somepony in the process. Hypothetically, see. Would that be a problem? Would I have to hear from anypony about it? Or can I trust you to deal with what I bring you?''

''I suppose so...'' Mac answered with uncertainty.

Rich wasn't impressed enough, it seemed. ''Now, Mac I will say right here that I'm gonna expect results and quickly too. I wanna hear you're serious, that you can get it done. I think this discussion's over now''. He held out his hoof once again.

''So, what'll it be? Yes or no?''

In spite of the more calculating side of his brain, Mac reluctantly held out his own hoof and shook on the deal.

Rich looked very pleased indeed. ''You just made a very wise decision, sir''.

''Signed your life away to be some rent-a-thug. Forward planning skills, dude''. It was only a hoof-shake though, not exactly a binding contract. ''Pa would'a disagreed''. Pa would've done a lot of things, his son being an outlaw for instance probably would've been something he'd want to address.

''If you say so,'' said Mac distantly, looking between Rich and the floor. ''Well, I'm still busy right now. You got further details?'' Rich shook his head.

''No, no, friend. This ain't work two ponies such as you and I just discuss,'' he gestured around him, ''not here anyhow. Be at Manehattan station one week from today: my associate will be there at about noon. Just wait once you're off the train and he'll approach you. I'll send him the word this afternoon. This kinda business is more his... expertise,'' he chuckled. ''Simple enough, am I right?''

''Eeyup''. '' 'Cept normally I kinda like simple plans''.

FIlthy Rich beamed at this. ''Excellent! I look forward to our families doin' business again, sir! I'll show myself out''.

''Eeyup,'' Mac muttered as the pony exited the barn.

Mac was an Apple farmer, not some lap dog for whatever kind of criminal mastermind Rich was professing to be. He had done things he wasn't proud of yes, he had acted immorally before and could do so again if needed sure but all he wanted was to get his life back on track so he could earn an honest living again. Now this? This was not where he wanted his life to go. He gave a deep sigh.

''Crap''.

(Present)

A cerulean mare with a rainbow mane, present in the large circular room of Princess Twilight's castle took a gasp and eyed Mac angrily.

''Wait, you stole my jacket?! That had all my medals on it, jerk!'' She leapt over and slapped his face with her hoof.

Mac recoiled from the impact, surprised that given the circumstances, that was something she felt the need to address.
''Uhh...sorry?''

''Oh, you will be sorry!'' She was engulfed by a magenta aura and lifted away from him by an annoyed-looking Twilight Sparkle.

''Honestly, Rainbow Dash, I really don't think this is a good time''. Dash pouted and folded her forelegs.

''What is going on here? Did Luna put you in a trance and now you're dreaming? This isn't what I'd expected''. Meh, that's just how Rainbow Dash was he supposed. Not quite as disturbed by the fact she was dealing with a hardened killer as the rest of them.

The Princess of Friendship deadpanned briefly, then returned her attention to her captive. ''I'm sorry to hear you went through that Big Mac, but I don't think it quite excuses what you've been charged with,'' she scolded.

Mac shrugged. ''No excuses, Miss. Just thought I'd come clean''.

Twilight raised her eyebrows. ''I see. So, if I remember the events correctly, this new 'partnership' didn't end up very well, did it?''

Mac smiled sadly. ''Nope...''