My Two Days Working in the Mob
They made me an offer they later regretted.
I’m not proud of the fact that I served in the mob. And I’m even less proud of the fact that I got kicked out of it after only two days.
It started, as many things do, with a game of Whack-A-Mole at the local Dave & Buster’s. It was “Free Wings for Emotionally Stunted Men” night, and I was on fire. After a waiter doused me with water to extinguish the flames, I was able to really concentrate on playing Whack-A-Mole. I was good — real good. Everything was clicking and I proceeded to whack mole after mole, my blazer still smoldering.
After a 12-game winning streak and some half-hearted applause from the jealous waitstaff, a man wearing dark prescription sunglasses and a fedora approached me and offered to buy me a drink (Whack-A-Mole is thirsty work, as any enthusiast will tell you). I accepted, and we slid into a booth, both blaming the upholstery for the violent fart noises we made as we did so.
We were silent for a while as we waited for the farting noises to die down.
“You’re pretty good at that Whack-A-Mole game,” the man finally said, leaning across the table. “But what if I told you you could get paid to whack off men?
I got up to leave, but he asked if he could start over.
“I didn’t say that right,” he explained. “I don’t say things too good sometimes. What I mean is, you could get paid to whack people off for the mob.”
Now he had my attention. I was, after all, down on my luck and desperate. My day job had just been replaced by a machine. Ten years of studying to be a conveyor belt down the drain — poof. Just like that.
I thought this mob offer might be the boost I needed until I was back on my feet and could go find a foot specialist to look at the bunions my feet.
The mysterious man, who went by the name “Toledo,” told me he worked for some very powerful people and that he also knew a very good foot guy who could take a look at my bunions.
“When do I begin?” I said, sipping my diet cola with relish.
“Now,” was the response, and suddenly a black bag covered my face and I was picked up and hauled away. I screamed and kicked until Toledo finally promised he’d doggy bag my leftovers. Then I was able to relax and fall softly to sleep in the mobsters’ arms.
Mob approval ratings
I was shaken awake in a dim basement — it was swanky, complete with a pool table, a bar and a china cabinet filled with little porcelain figurines.
I was introduced to the leader, “Fat Nino,” who I quickly learned prefers just “Nino.” Same with “Big Nose Larry” and “Underdressed Nathaniel.” “Crooked Tooth Sally” suggested maybe I was projecting my own insecurities onto them, and I said I didn’t think so.
Things were off to a slightly tense start, but they softened when Toledo began to tell them about my Whack-A-Mole prodigiousness.
“Toledo, you idiot,” scolded “Jealous George.” “How many times do I have’ta tell ya that dumb game ain’t the same as workin’ in the mob!”
Toledo looked a little embarrassed and so I felt I had to prove myself so they wouldn’t all think he was some kind of moron. Thinking quickly, I picked up some of the pool balls and started juggling them. I wish I hadn’t, because I immediately remembered I don’t know how to juggle. But Toledo’s reputation was on the line — I had to be bold.
I tossed the balls in the air and, wouldn’t you know it, the 6 ball came down right on “Dumpy Malachi’s” head, knocking the poor sap out cold.
Fat Nino seemed impressed. He nodded approvingly as I took a well-earned curtsy. I started Monday.
The student becomes the mobster
The mobsters paired me up with Toledo for on-the-mob training. I asked him a lot of questions about being in the mob and he was a pretty open book. He said it was stable work, and he liked that you got to travel a lot and choke interesting people.
It involved a lot of moving furniture in and out of apartments around the city, and after a few hours it didn’t seem that much different from working for a moving company. But Toledo assured me that this was just a cover and an important part of being in the criminal underworld. Then he winked as he placed a customer’s Star Wars Funko Pop in his pocket and whispered “Don’t tell.”
After a lot of hard work and a disappointing amount of tips, Toledo informed me it was time to do some “serious” mob work: harvest the “strangling strings” from his grandmother’s upright piano.
Well, we took a trip to his grandma’s house out in the suburbs. When we got to the piano it took a while to figure out how to open the top up. I couldn’t help tickling the old ivories absentmindedly while we worked, and before I knew it Toledo was running upstairs to get his oboe so we could write a rock opera together.
We called it “Wonder of the Stars,” and it was about an alien with the gift of “true rock” who crashed on earth and had all kinds of wild relationships while searching for “the one” who could translate his music so it could be understood by humans. We worked on it until Toledo’s grandma got home and told us it sucked. Then we pretended that that was the whole point and that we were just goofing around and being ironic about it.
Then Toledo went into the bathroom for a long time and when he came out his eyes were all red.
By that point his grandma had cooked us both a huge plate of veal parmesan, which she said was made using a recipe that had been passed down by previous generations; they kept trying to pass it back up, but the previous generations had gotten savvy and wouldn’t take it.
We ate in silence, insanely hungry from all the physical work that morning and our mentally draining creative process. When we finished, Toledo’s grandma told us to rub our bellies for half an hour so everything would digest properly. Toledo argued that we didn’t have time, but relented, and we both ended up napping for 8 hours.
When we awoke, there was a hand-written letter on the porch from Fat Nino:
Importnt missn. Meet to tlk. Pen rnning out of ink.
The call had come, and after a full day of training, Toledo said he thought I was ready to tackle a mission on my own. It was time to get to work. But first, breakfast.
A mob well done
The job was a pretty easy one, all things considered. I just had to deliver a fish to a neighboring mob’s house. Fat Nino said it was a way of “sending them a message.” Seemed passive aggressive to me, but sometimes you just have to pick your battles at work.
I finished the task early and decided to call it a day. I was lounging in the park and looking over the notes for “Wonder of the Stars,” pondering where we went wrong, when I got a random text from Toledo:
Meet me @ pier n 1 hr. Pen rnning out of ink.
Now, Toledo had spent about an hour the day before explaining that they took “Fredos” to the special mob pier to nix them and then chuck them in the river. Why would he want me to meet him there? I was super curious and also pretty bored, so I texted him:
BRT! should I bring my undercover cop friend? lol jk.
I arrived at the pier three hours late (stopped for a quick suit fitting), and saw Toledo pacing nervously.
I lumbered over. “Hey, Toledo,” I said. “So I was looking over the music again, and I think — ”
“Shut up!” Toledo snapped. I was taken aback. Where was this rudeness coming from? Maybe he’d learned it from his grandmother, I thought. There’s a time to be blunt and a time to be gentle, you know?
“You screwed up big time,” Toledo continued. I tried to think about all the mistakes I’d made in the past 48 hours, but there were so many I couldn’t settle on just one guess. So instead I decided to pretend I didn’t do any screwups at all and just act confused.
“Huh?” I said. “What ever are you talking about?”
“This!” Toledo said, and he held up what appeared to be a thank you note from the mob family I’d delivered the fish to that afternoon.
We just wanted to thank you so much for the fish you had delivered here this afternoon. I don’t know how you did it, but it was fried to absolute perfection. Our crew can’t stop talking about it! I don’t say this often: it was life-changing. Was that cajun in the sauce? In either case, your kind gesture has made us rethink some things and we’d like to meet to discuss peace.
All the best,
P.S. If you ever need any pen ink, it’s on us.
“So what?” I said. “I did my job. Plus I got a great DoorDash rating.”
“You idiot!” Toledo continued, getting ruder every minute. “You were supposed to deliver it dead and wrapped in newspapers, not cooked and seasoned to delicious perfection! You made us look like fools! How could you do this to us?”
I couldn’t believe the way Toledo was speaking to me. Is this anyway to talk to a junior mobster trying his best? It cast the entire industry in a new light and, frankly, I began to wonder if this job really valued my talents at all. Then I started to wonder if this job was right from a moral standpoint (no recycling). Finally, I started to wonder what I was going to do about the pizza cutter Toledo was shakily pointing at me.
“Now I’ve got to do something I didn’t want to do,” he said. “Nino wants you gone — for good. And he also wants to know what the hell you did to that fish to make it so good.”
“Toledo, you don’t have to do this,” I said, realizing that he probably had to do this, because at this point there was no way I’d ever forgive him if he let me live, even if he said “I’m sorry” like a million times.
“It’s not personal,” he said, taking a step toward me. “It’s just business — mob business.” And with that, I watched as a long katana shot up from a hole below the pier and ripped through Toledo’s chest.
Toledo dropped to the pier with a thump, like a bookshelf of blood. I stood there, stunned.
“No one steals Funko Pop from the Pinocchio family and gets away with it,” a wise-guy voice shouted from below me. “Now we’re gonna come up there and kick your ass!”
I watched with horror as multiple wet mobster heads began to poke up from beneath the rickety pier. This is the end, I thought. But then — like the dark, surrounding waters — a strange calm washed over me.
Unthinking, moving with instinct now, I picked up a rotted plank and proceeded to whack the angry heads popping up, one by one by one. I moved with a practiced finesse and efficiency — when one went down, I hit another, then doubled back for the return of a previous head. There were dozens of them, but the more I whacked, the better I became, drawing strength from their groans and chattering.
It took six hours, but I won — I’d whacked until there were no more mob heads peaking up to whack.
Once I was sure they’d given up, I dropped the plank and sank to my knees. The sun was setting over the water now, and I wondered if I’d be able to make it back in time for The Masked Singer. Just then, I heard a moan.
I crawled over to where Toledo lay and propped his head up in my hands. But his hair was all gross and sweaty so I laid it back down and just kind of looked at him from the side.
“I’m — I’m sorry,” he coughed.
“Uh-huh, but sorry for what?” I said, wanting him to say it.
“I’m sorry I tried to kill you with a pizza cutter,” he said. “I’m sorry a million and one times.”
Without warning, my eyes filled with tears.
“I forgive you,” I said.
“Look,” he continued, kind of ruining the moment for me. “Remember how the alien from ‘Wonder of the Stars’ didn’t know how to communicate his music to earthlings, and needed to find ‘the one’ to help him?”
“Well, deep down, I’ve always felt that, in a lot of ways, I’m that alien,” he said. “And, well, I think you’re my ‘one.’”
Now we were both crying.
“I want — I want you to continue on with ‘Wonder of the Stars.’” he continued, fighting for air. “I want you to tell my story.”
“I will,” I sobbed, my salty tears splashing through the cracks of the pier, adding to the ancient, mysterious sadness of the earthly waters below. “I mean, we kind of wrote it together, but I’ll definitely give you half credit for it.”
“Send it to Tony Bennett,” he coughed.
“Tony Bennett? That’s kind of random,” I wailed.
“He’s the best,” Toledo said. “The best!”
And with that, Toledo died the way he lived — wrong.
But despite all the trauma and dry cleaning bills those two fateful days with the mob left me with, I still very much regret my time with Toledo, not to mention all the other zany mob characters I met and whacked along the way.
And I guess the reason I’m writing all of this to you now, Mr. Bennett, so many years later, is to remind you that you never know what horrible things you’re going to experience when you make an uninformed decision out of desperation and greed.
So, read the attached ‘Wonder of the Stars’ outline. And enjoy the attached fish.
You won’t regret it.