The Fantastic Adventures of Will & Grayson The story of two G-Men and their crime fighting escapades. Volume #1: The Pint Sized Bootlegger

Entry One: Will

The Ford Model T, or more commonly known as a Tin Lizzie. Sporting a wide array of colors like black, black, and just black.

It was one hell of a ride to Chicago, I'll tell ya. These Tin Lizzies are way too small for my comfort, and I could tell I was in the wrong neighborhood as soon as I stepped out of the car. I guess I had the look about me, then. They don't bother even cleaning up around here. The streets are trashed, and there are seedy sorts all around us. Some bent Airedale almost tried to mug me! Luckily, his little vamp knew better and pulled him back before I laid him out. Grayson knows this city better than I do, but that doesn't mean I'm taking crap from any sap here just because Grayson has "connections". Anyways, we must look like some private dicks, because we didn't get lip from anyone else. I mean, not a thing on our ol' boy Sledgehammer. Grayson might have, though.

Entry 2: Grayson

The man was old, waiting for the world to give him a break that would never come.

I've read over Will's entry, and he's about right: people are awfully protective of each other in this neighborhood. However, when he was tussling with that brute, I managed to pick up a lead. I almost missed him too, had he not asked for some change. I gave him a nickel and looked him over. He was obviously an alcoholic, so I asked him where I could get a "quilt" on this cold night. He spat out some unsavory goo and told me the whereabouts of a guy that supplies him when he has the cash. Said the guy works for Sledgehammer - that is, Harrison Dawes, or Sledgehammer Harry as he is called by the locals. I thanked him for the info, and all of the color drained from his face. I guess he realized I'm a federal agent, because he shushed me. I looked around and spotted some baby grand on the corner with a fag hanging lazily from his mouth. He looked straight at me, and walked off. I walked back to Will, who was still in a lather about being assigned here. I hope this assignment goes better than the last, because I'd rather not shoot anyone if I can help it. It's a lot of paperwork nobody will read.

Entry Three: Will

The Classic .35 S&W Auto, the same gun that federal agents at this time would utilize.

Yes! That tip Grayson got must've been the best break we've ever had working with the feds, because that guy the drunk turned Grayson onto was a total pushover. He broke as soon as we walked in the door, and started begging for us not to let him go. Obviously confused, we sat him down and demanded he told us what he knew. "I didn't mean to get into this business, I swear!" he said, blubbering all over the place. Grayson managed to calm him down and he told us everything he knew. He claims that he gets his bootleg booze from Sledgehammer's right hand man, "Skinny." He also mentioned that the house they get it from supplies their entire operation; we're talking the works, too: stills and all. Man, from the sound of it, we're gonna need some backup. Hope this guy ain't fibbing, because if he is, this whole deal is going to go bad VERY fast.

Entry Four: Grayson

A lot of people (like Will, for instance) cared not for the ban on alcohol.

Again, I've read over Will's entry, and it seems that he always misses something that happened. Probably "examining" the whiskey, I imagine. Regardless, we went to the warehouse that the homeless man pointed us to and we caught the guy dumping that foul coffin varnish out the window, obviously trying to get rid of evidence. This seemed to particularly irritate my partner, so he pulled him in and threw him in a chair. Tommy, as he told us after Will frightened him, was one of the distributors for the North Side Gang, working under "Skinny", whose name isn't on file. Interestingly enough, he also informed us of one of the warehouses being used as a distillery, to which most of the supply goes to a speakeasy hidden around town. I'm hoping the location of this speakeasy is at the warehouse, otherwise we've hit a dead end here.

Entry Five: Will

Both the local law enforcement and the feds got rid of bootleg liquor anyway they could (save drinking it).

Wow. Just as I was hoping for a day off. Things started off a little wonky, as most of our back-up didn't even show up. The police department said they were "booked." Sounds like a load of bull to me, but we did manage to get a couple of cops to show up and we busted in. Unfortunately for them, they weren't expecting this kind of attack early in the morning. Most of the guards were asleep, with tons of bottles all over the place. However, a couple of conscious guards were about and asked us to leave ("Private property, old boy, now beat it!") with a bribe if we were cooperative. Ten minutes later, one was dead and the other one was tasting the pavement. Don't threaten me. Anyways, we made a deal with this gentleman: tell us the info we want, and you get a one way ticket out of this city. Eventually, he cracked after a measly two hours in lockup. We're hitting a speakeasy tonight, and hopefully putting Sledgehammer behind bars (or in the ground) by tomorrow.

Entry Six: Grayson

What a mess. This morning's raid did not go as planned. Most of the officers didn't even show up. They said that they were just too busy, but I know this place: corruption is at the heart of half of these officers. What few that came were veterans, so that gave me enough confidence to continue through the building. We must of locked up ten guys that were just lying on the ground, fast asleep. There must have been a party, because there were bottles strewn across the facility. Too easy. Regardless, we only ran into two guards that were even awake, let alone patrolling. One didn't bother even talking to us, as he ducked behind a corner and opened fire on us. One officer got hit in the shoulder before I hit the assailant in the chest. He crumpled in the distance, and we pushed into the office, where the manager was having a cup of coffee. We had our guns trained on him, but he offered to forgive us for "breaking into his place and killing a very experienced employee." Will wasn't having it, and punched him in the jaw. Of course, in the reports, he pulled a gun on us and we had to use extreme force. We dragged him outside, where Will and the manager made a deal.

Entry Seven: Will

Gah! That two-timing snake charmer! I love flappers, but man do they get me in trouble! To start with, we went to a barber shop on some street long run down. There was only the owner there, who motioned us toward the door with jerk of his head. Grayson knocked on the door with a particular tune, and a hidden door was revealed. Some bent greeter ushered us into the room, where I met a choice bit of calico waiting by the bar. Grayson told me to blend in and wait for backup, so I did. She and I got to talking, and she got a little excited and asked me to come to the back room, with a kiss and a wink. I'm just a man, how could I resist? Well, she must've left her girlish attitude by the bar because when I entered she knocked me on the head with something. I came to by the time the place was cleared out. I had no pants and both my wallet and sidearm were gone. I'd say that now she knows that I'm a fed, Sledgehammer is gonna go back into hiding. Plus, Grayson is still laughing about the whole incident while I'm writing this. I'll never live this down, I swear it.

Entry Eight: Grayson

Why do I even bother? Classic William, caught with his pants down in the back of a bar that shouldn't even be there. When we entered the place, the greeter mentioned something about Sledgehammer actually being there. Of course, I told Will to just act natural and get ready for backup. By the time I came back from the police department, the place was nearly gangster free. Of course, there was one poor sap in the bathroom that we took into custody. He gave us the location of Sledgehammer's safe house after he realized how much his "family" cared for him. He asked not to be detained, as if he was still in Chicago after Sledgehammer was taken down, he'd be bumped off within a week. I let him go eventually and the officers thought I should see something in one of the back rooms. Well, I found a passed out William sitting in a chair with his hands tied and his pants gone. I flicked him in the forehead and he woke up. The first expressions on his face was surprise, then disappointment. Will told me all about it, and I assume that the dame was working for Sledgehammer. Women were always good about telling a man's true nature, and this one must have spotted Will right away. We are en route to Sledgehammer's safe house as I write this. Hopefully the next entry in this journal will be one of celebration.

Entry Nine: Will

God, I love this job. There is nothing that feels better than bagging a big one. Unfortunately, Grayson sustained some heavy injuries, so Lieutenant Davis will be filling in for his part in this entry. Our boss would like a perspective from each agent, but Davis was close enough to give a good report. Davis, Grayson and I breached the house, expecting only a couple of guards. What we got was a fresh hell. I guess they were expecting an attack, because we must have killed ten people just at the front room. None of them could shoot well enough, which I guess is why they were the first to have a go at us. After those guys, we gathered some weapons from the fallen gangsters and continued through the house. We found out the hard way that not all gangsters are terrible shots, as Davis caught a bullet to the leg before we were able to take down his bodyguards. Davis stayed behind to cover the door as we entered his bedroom. Let me tell ya, this Sledgehammer guy was not exactly what I was expecting. The guy swung at us as soon as we opened the door. Funny thing is? This guy was a freaking gnome. Must have been a little above my waist in height. His favorite toy, the sledgehammer, caught poor Grayson right in the ribs, causing him to drop to the floor screaming. He managed to hit him in the thigh with another swing before I had to put him down. The whole damn thing was a mess to be honest, but I got the bad guy. Ol' Sledgehammer Harry tried to be as big as Capone, but he came up a little short.

Entry Ten: Lieutenant Davis

Davis here. This whole thing is going to go up in local history as one of the most violent raids ever done by police around here. I guess I am happy to be a part of cleaning up the streets, even if I am putting myself in more danger by trying to fight the gangs instead of letting them just run free. The raid was botched from the start, now that I look back on it. If we had more men, we may have been able to make them stand down. However, like Grayson would say, corruption has taken hold of some of those behind the badge. We managed to take care of two threats behind the booze operation in this part of the city: Jack "Skinny" Moriarty (his body was identified as one of the bodyguards) and Harrison "Sledgehammer" Dawes. Both former saloon owners turned "criminals" by prohibition. What a load of bull, I say. However, the law is the law, and it's my job to enforce it, even if I get paid a miser's fee for it.

Created By
Gabriel Petree


Created with images by jon rubin - "The Untouchables" • katherinetompkins - "1923 Ford Model T" • Leon F. Cabeiro - "Where Have All the Good Times Gone?"

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