Rudy
Rudy was the manager of the bar where I worked part-time for four years. The bar was part of a restaurant and country inn that was built inside an old estate home on a little hill. There were four of us: two other bartenders, me, and Rudy. Whenever Rudy didn’t want to work a shift, he’d leave us a tidy little gram of cocaine slipped underneath the stack of 20s in the cash register drawer. We’d pick it up there before our shift. Rudy never worried about anyone discovering what he did because he was supplying just about everybody who worked there with blow. It was a perfect marketplace. He didn’t need to go looking for customers they came to him.
I wasn’t interested in the coke Rudy left for me on the few shifts I covered for him, so I’d give it to the waiters. They always knew when I was covering for Rudy, and they’d be right there hoping I’d slip them the little packet. It wasn’t sly or mean or anything, they just wanted to be around and make sure I had someone to give it to since they knew it wasn’t my thing. They were always grateful and it was comforting to know that, at least to some degree, they were indebted to me for the night. Later on in the evening, they might be a little more patient when there was a rush and all of them were lined up at the counter asking for drinks.
I took the job because I needed one. A few months earlier I’d dropped out of graduate school unsure what to do next. So there I was, a bartender working for a drug dealer. At the time, I thought it was a little unusual and part of a secret world I knew little or nothing about. It was only later I discovered that, really, none of this was that unusual.
The inn, restaurant and bar were a place where rich people could eat, hang out, relax and make a deal or two. All of it built up or “restored” inside the shell of a 100-year-old building. It was intended to be a pseudo retreat for the CEOs that lived in the neighborhood but really it was more like a mix between a cottage at Versailles and a Southern country home. There was money, gossip, great food, and even better wine. Pleasure was the name of the game, and everyone who worked there and everyone who came there knew it.
Rudy, as manager of the bar, was responsible for ordering and maintaining the wine collection. This was a bad idea. Bad because whatever work he was given was seen as another opportunity to grow his little empire. In this case, for every dozen cases he ordered Rudy became very good at making sure that a case or a few bottles would go ‘missing’ and then pointing back at the vendors and letting the owners know he was “looking into it.”
The owners of the restaurant were a different species altogether. Two ladies in their sixties. I call them ladies because that’s what they asked us to call them. “The ladies”. Talking to them was like being thrust back a hundred years or so into late Victorian England. I remember during my interview sitting bolt upright on the edge of my chair, and holding myself in that position, spine ramrod straight, for the twenty minutes they spent with me. When they’d ask me a question I’d slowly turn my head toward each of them as they spoke, lowering my eyes and nodding my head in gestures of agreement and deference like something I’d seen on episodes of “Upstairs, Downstairs”. It was an odd feeling, utterly out of body. Looking back, I’m not sure what was going on, but if I were to venture a guess, I’d say it was like falling under the spell of a powerful fantasy invoked by the desperate attempts of these ladies to create some sort of sanctuary from the misery of being married to their rich, otherwise engaged, husbands.
The ladies LOVED Rudy. After all, he was still young, early thirties, tall, good looking, dark hair, dark eyes and I’m sure he had no problem being deferential to them with a hint of rebelliousness that might inspire a fantasy or two. For all I knew then, maybe he was giving them blow too. I don’t know. But what they said to me at the end of my interview was that I was to take my marching orders from him and do whatever was asked. Having not met Rudy at the time and considering the alternative of taking guidance from this retro-Stepford pair, I was more than happy to oblige.
The first time I met Rudy, he was behind the bar. I call it a bar, but it was really a small room inside the old house where someone had installed a 14-foot-long service bar with an ice bin at the end where the bar curved around with a flip top for getting in and out. It was the end of the lunch shift, and waiters were coming in and out asking for drinks, and Rudy easily poured or concocted what was needed while talking to me about the job. He was not overly friendly and mostly focused on scoping me out. The transition was jarring, having just come from being interviewed by the royal court to feeling like I was standing on a street corner in front of a Seven-Eleven being vetted to see if I could be trusted.
Nonetheless, I seemed to have passed whatever criteria both the ladies and Rudy had in mind and I was in. I had a job. I was the new bartender.
Bartending at the place was pretty easy. Essentially, you were a back-barman since the bar itself had no real counter service, although it did have a few small round tables in front of leather-wrapped, cushioned benches where couples could come in and sit and have an aperitif while waiting for their table. Occasionally, 2 or 3 couples would wander in before dinner, hang out, have a drink and leave a tip. But for the most part, the job consisted of making sure waiters got their drinks in a timely fashion so customers could have a couple of drinks, run up their bill, and leave a bigger tip.
Rudy was always relaxed. I don’t think I ever saw him hurry or sweat over anything. He never took shit from the waiters and didn’t worry too much about who he pissed off. At the end of the day, he knew they would come to him for what they wanted. Aside from the money he made dealing, Rudy was earning a decent income selling the ‘extra’ wine he ordered. It was a nice set-up. No need to hustle out on the street; all of his business was right there, and there were really no visible threats that I ever saw. Which is why I was shocked when I found out that Rudy carried a gun.
It was a little one. A 2-shot derringer that fit in his pocket. As far as I know, he never came to work without it, but he also never had any need to take it out, nor did he. He told me about it one day before lunch service started. I was sitting at a table by myself, eating my grilled cheese sandwich. I usually sat by myself because most of the wait staff spoke Spanish and liked to chit-chat at lunch and it felt creepy sitting at the table not knowing what anyone was saying.
Rudy said, ‘So you live in the city?’
‘Yeah’
“Do you carry a gun?”
“What?”
“Do you carry a gun?”
“Uh, no.”
“Hmm, might be a good idea, I mean, you never know, right?”
“Well, yeah, but I don’t live in a bad area. It’s close to midtown, there’s hardly ever any trouble and I’ve never heard any gunshots or anything.”
“Ok, yeah, but still, you never know, right”
“I guess”
“I do”
“What?”
“Carry a gun.”
“Really?”
“Yeah, it’s in my pocket.”
“Here?”
“Yeah.”
And then Rudy stared at me like there was some message he was trying to convey. I looked him in the eye for a few seconds and then went back to my sandwich.
Later, after the rush of lunch service had quieted, one of the waiters, Albert, came by the bar to hang out. I couldn’t resist asking,
“Hey, did you know Rudy carries a gun?”
He chuckled gently. “Oh, yeah.”
“He told you?”
“He showed it to me. I think he wants everyone to know. This is not surprising my friend. Rudy wants everyone to know he’s a bad hombre.”
“I guess”
“Don’t worry my friend, it’s a little pistol thing like girls used to carry in the movies.”
“Like a Derringer?”
“Yeah, that’s it!. You’re a smart kid. You like the movies?”
“I guess.”
“Don’t worry about Rudy’s little gun, ok? He’s got no reason to take it out here but he’s a paranoid little motherfucker so keep your distance.”
And that was how I found out about Rudy’s gun.
At first I couldn’t help thinking about it. I’d never known anyone that even owned a gun, much less carried it at work. I had friends who became cops but I’d never hung out with someone who casually walked around with a gun in their pocket while they did their work. After a while I forgot about it. Rudy never mentioned it again and I never brought it up, so eventually it was like it was never there.
During that first summer Rudy let us all know he had a new girlfriend. The girl’s name was Daisy. None of us had ever met her but we’d seen her several times when she dropped Rudy off at work and drove away in her little red Miata. “She was a looker” was what Albert said to me during a shift. It was an old expression from the movies and it sounded funny coming from him but it did capture the mystique we all sensed.
She was blonde, always dressed nice and whenever she dropped Rudy off she always kissed him. It was clear how he felt about her from the look on his face when he would get out of the car. He was dumbstruck in love. Each time he got out of the car it looked like he was coming from an out of body experience. Another world. And somehow in the transition between the car and stepping onto the pavement the look on his face would change from the world of their love back to the cool look of suspicion he usually had, looking left and right, being careful to clock whoever was watching.
While Rudy was suspicious of everything and everybody he was never shy about telling us how great she was and how their sex was hotter than hot. Those were his words. He would never share details but always described it in those terms. The “hottest of hot” and “super hot” and things like that. He also talked about how nice she was, how she’d do all these little things like putting flowers in a vase, placing it on the counter in front of their kitchen sink. How nice it was to live with someone who liked to do all those little things that made life better. He was crazy in love there was no better way to put it. I’d never seen anything like it before.
One day, while we were doing the wine inventory and sticking the odd bottle in his “special box” he told me he was going to ask her to get married. It surprised me. Rudy and I were not close. I only saw him at work, at most maybe once every other week, when some form of inventory or maintenance was needed at the bar. Most of the time I came in to work, did my shift and got back on the train and went home.
Rudy was sitting on some crates and I was counting bottles in the wooden storage cubes when, with no lead, he said,
“I’m going to ask her”
“What?”
“Daisy”
“Yeah”
“To get married”.
“Wow. Really?”
“Yeah.”
“I love her.”
“That sounds great.”
“I got a ring.”
“Yeah?”
“See” Reaching into his pocket he pulled out this little golden-pink band with a single diamond at the top.
“It was my grandmother’s.”
“Oh”
I was surprised to see him carry the ring this way. It looked fake. Like he’d gotten something out of a Cracker Jack box and stuck it in his pocket. But when I looked close I could see it was real. He held it up to the light for a minute and we both looked at it. Then he put it back in his pocket.
“So what do you think?”
“What?”
Rudy never asked my opinion about anything. Even stuff at work. So to be asked about something in his personal life left me speechless. I needed a moment…
“About me getting married.”
“Oh, well, it sounds great. Sounds like she’s a great girl. You guys have a really good thing together so why wouldn’t you do it, right?”
“Hm. How many Lafite?”
“What?”
“The bottles.”
So anyway, that’s how I found out Rudy was going to ask Daisy to marry him. Of course the talk that night amongst the waiters at service was all speculating when Rudy was actually going to ask her and if he would actually see it through and get married. There were a lot of riffs about how successful a marriage would be for the gun carrying, drug dealer/wine thief and wondering how much Daisy knew about how Rudy made his “living”.
I think Rudy was a more serious person than most of the wait staff gave him credit for but I never really got to the bottom of it. One reason I thought this was because one night later that spring, I came to work and found a little package, gift wrapped, on the bar with a card addressed to me on top. It was carefully wrapped with this paper that had little soldiers on it. I opened it and inside was a book, “Meditations” by Marcus Aurelius. I had never heard of it. I flipped open some pages and it looked like some kind of diary or something.
I read a few sections,
In a sense, people are our proper occupation. Our job is to do them good and put up with them.
But when they obstruct our proper tasks, they become irrelevant to us-like sun, wind, animals. Our actions may be impeded by them, but there can be no impeding our intentions or our dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.
The impediment to action advances action.
What stands in the way becomes the way.
I had no idea what to think. I set it aside and went about my shift and only thought about it at the end of the night when I was closing up. I grabbed it before I left and opened it up on the train. It was a revelation to me. The diary of an emperor, it was filled with insights, many of which spoke to things I’d been struggling with for some time. I loved it but could not figure out for the life of me how Rudy would have known that this book would speak to me the way that it did.
I never had any personal contact information for Rudy and in those days there were no cell phones or internet so I had to wait until the next time we were doing inventory to ask him about it.
“Thanks for the book.”
“Welcome. Look over there,” pointing to some bottles on the floor, “I think those are Jordans too.”
I picked the bottles up and put them in their proper shelf.
“So, how did you know about the book?”
“What?”
“Have you read it?”
“No. I just thought it sounded like you. You know, thinky, like the stuff you read in college right?”
“Yeah, Ok, well thanks, It’s great, you should check it out sometime.”
“No thanks”
And that was all he had to say on the subject until later that night, after service, Rudy came back to the bar as I was closing up. He looked a little frazzled, like he’d been running or something, he was sweating and his clothes looked like they weren’t fitting right.
“Rudy.”
“Hey.”
“What’s up? You ok?”
“Sure, yeah, I’m good, just need to sit for a minute.”
He sat down at one of the little tables in the bar and looked out the window. He was lost in thought or memory, I’m not sure which but I waited and went about my business closing up the bar. When I was done I came out from behind the bar and he looked at me and said,
“Alexander.”
“What? Who’s that?”
“You know, the king”
“Oh, right, that Alexander.”
“He had it right, you know…no matter how hard it is, how far you have to go, whatever you have to do, you have to give them what they want.”
“Hm”
“He took over when he was 20.”
“Yeah.”
“He understood what had to be done and did it. He only knew one way and did not hesitate. Took over cities, gave them what they wanted and moved on. He understood what he was doing. Those wars were bloody and horrible and still he kept right on going knowing what he was doing was right.”
Rudy stared out the window for a long time. Like he was remembering something, trying to piece it together. Finally, I said,
“Rudy?”
He turned, “huh?”
“Ok if I close up?”
“Oh, yeah, sure. I think I’m gonna ask her on Friday.”
“Oh. Wow.”
“Yeah.”
And that was it, he stood up, looked at me and said, “Good night” and walked out.
After that night, I didn’t hear from him for like two weeks. It was a little strange given the normal cadence of things around work, but I didn’t think too much of it until one Tuesday night I was working dinner service when he comes walking into the bar, his right hand all wrapped up in a bandage. I mean completely wrapped up around the wrist and thumb and up and over the index finger. I asked him what happened and he said, “I cut myself on a bottle that broke while I was loading in.”
“Oh, shit”
He smiled at me, “No biggie, had to get a tetanus and whatever but I’m good now.”
“Ok, well that’s good”
Then he looked around for a bit and was gone.
Later in the shift, near the end of the night, one of the waiters, George, came by the bar and stood as close as he could and said in a low, neutral voice
“Did you hear what happened to Rudy?”
George was a gay man in his mid-fifties and thoroughly enjoyed gossip. If he couldn’t get a hold of something that was true then he had no problem hinting at something else that maybe wasn’t.
I said, “Yeah, I saw his hand. He said he cut it on a broken bottle.”
“No, I mean, what really happened.”
“Oh, no, what was that?”
“Rudy shot himself.”
“What?”
“He shot himself with his little gun.”
“Shit.”
“Yeah and Webster’s husband patched him up.”
“Webster” was Mr. Webster, husband of Joanne, one of the ladies. He was a plastic surgeon.
“No shit, really? And they didn’t fire him?”
“No.” (George had a smirk on his face you could read a mile away)
“What?”
“Well?” George said, in possession of some kind of knowledge well beyond my ken.
I said, “Well?”
“Well, why do you think he wouldn’t be fired?”
“I don’t know.”
“That’s true, but Rudy does.”
“Rudy does what?”
“Know something.”
“Oh, shit, about the Websters? Oh man, that’s wild.”
“I know” (now George was in full smile)
After that there was a ton of speculation going around. Everyone you spoke to or even looked at had it on their mind. What actually happened? Was someone else there or was he on his own? And why did Webster patch him up and send him home instead of firing him on the spot? What did Rudy have on the Websters?
When you are in your twenties, for most of us, you have very little idea of what actually goes on all over the world on a day in, day out basis. I mean, you think you know or at least have some clue but the truth is you don’t. You can’t believe it. It’s too much and so if you want to appear ‘worldly’, you accept the wild things you’ve seen or heard but for the most part you tend to think of them as blips, little fragments outside the norm but the norm, you tell yourself, is for the most part just that – normal. Not much happening. Just people being good and nice and trying to go to work each day, do their jobs and get ahead, little by little. But, of course, that’s not really how it is.
When all this went down I was so shocked at the idea that I was working at a place where my boss had shot himself in the hand with his own gun, I really had trouble piecing it altogether until one night I had to take some drinks up to a room in the Inn. This was not uncommon. Sometimes the Inn guests wanted a cocktail brought up and we were more than happy to help because the tips were usually good. I had delivered the drink and was turning to walk down the hall, not really thinking about anything when it hit me. Four months earlier, when I’d started at the bar, I had taken some drinks up to the same floor and bumped into Rudy in this same hallway. He’d been coming out of a room, the top few buttons on his shirt unbuttoned and carrying 2 empty wine glasses and a bar tray.
“Oh, hey, yeah, cleaning up after some guests.”
I looked at him, knew he was lying, and looked away quickly.
“Can you take these down to the bar?” he said, handing me the tray and glasses
“Sure”
“I’ll catch up with you after the shift and we can go over how to do inventory ok?”
“Sure, sounds great.”
That was it. Rudy had been in that room with someone, and it wasn’t too hard to draw a line from “someone” to the possibility that that someone was someone at the Inn and to the possibility, given Mr. Webster’s reluctance to fire Rudy or call the cops, that the someone in question could have been Joanne Webster.
All of this became a lot more solid in my head when I started chatting with George during the dinner shift and hinting at what I’d seen. He was more than willing to come forward with an opinion
“I think something’s been going on between them for months.”
I thought, Months! Holy shit. Where was I? Does this kind of stuff go on everywhere? Where the hell am I working?
After I’d digested all this and my life in the city. the things I’d seen walking those streets for a year, it all began to feel like this was the world. Everyone hungry for something, willing to do about anything to get it. I can’t say it was life-changing but it certainly changed the way I looked at the people around me. Like they were all in on something and I had to make up my mind if I wanted to be part of it or maybe I was part of it already.
All this was going through me as the end of summer was approaching. I had decided I would give graduate school another try and I wasn’t sure how much longer I was going to keep working at the bar. I was at the Inn, sitting outside behind the kitchen, talking to one of the busboys, when Rudy drove up and parked. It was a little strange to see him driving his own car and the busboy said, “yeah, no Daisy.”
Rudy parked, turned off his car and sat there looking out the window for a minute. I walked over and he rolled down the window and said, “Get in”. So I did. At first we sat there in the car, not saying anything. It was awkward. 2 guys sitting there, no words, just staring out at the trees on the property. Then Rudy said,
“I’m going to tell you something but you can’t tell anyone ‘till I’m dead.”
“OK”
“I mean it.”
“OK”
“Daisy broke it off.”
“Shit. Rudy.”
“Nah. “Is what it is, right?”
“Yeah. I guess, but it still sucks. When?”
“You know that Sunday about a month ago when I said I was going to go in and do the inventory?”
“Yes.”
“She dropped me off like normal but then like 5 minutes later she came into the cellar and said she was done, it was fun and sorry and bye.”
“Shit”
“Yeah. I lost it for a minute you know, watching her walk out, up those steps, I couldn’t believe it, everything was so good. I freaked out and reached into my pocket for the ring, thinking this would show her you know, that it wasn’t a casual thing for me, that I loved her, that I meant it, that it was real.”
“Yeah”
“Then the gun went off, and she screamed, and the fucking thing hurt so bad I had to do something, so I yelled, “Daisy!” and then I pulled out the ring from my pocket. But she just looked at me and my bloody hand. Then she left.”
“Shit”
“Yeah. Fuck her.”
“Yeah.”
“I still think it was real.”
“Definitely”
“What we had.”
“Yeah”
“But you never know right?”
“I guess.”
After I said this, we sat there in the car for a while, then I got out of the car and shut the door. I waited for Rudy to get out too, but he didn’t. Eventually, he started the car, backed out of the parking spot and slowly pulled out of the driveway. That was the last time I saw him.
A month later, the Maitre’d of the restaurant asked me if I’d be interested in ‘managing the bar’. He said he would take over inventory and ordering, and all I would really have to do is work three days and ensure we had enough qualified bartenders to staff the place when I wasn’t there. I said I was going back to school, but thought I could handle it and so that’s what we did. I worked there for another 2 years then moved on.
I hadn’t thought much about the place in the last 40 years until I saw this obituary online. It was from the local paper.
Rudolpho Valentino Degregorio, (1955 – 2025) a beloved bar keeper, mentor, and friend to many, passed away at the age of 70. Known for his steady presence behind the bar and his unmistakable warmth, Rudolpho dedicated his life to giving people what they needed at work and at home.
Rudolpho, owner of “Harry’s Place” a beloved watering hole on Second Street for more than twenty years, was more than a barkeep—he was the heart of the room. With an easy smile and an encyclopedic knowledge of spirits, stories, and people, he had a rare gift for turning strangers into regulars and regulars into family. He took pride in his work, believing that a well-run bar was built not just on good drinks, but on respect, consistency, and care for others. Many who worked alongside him credit Rudolpho with teaching them not only the craft, but the values of patience, professionalism, and kindness.
Outside of work, Rudolpho was known for his generosity, particularly with kids and the homeless. He carried himself with quiet dignity and a sense of humor that could lighten even the longest night. His presence will be remembered in the laughter shared across the bar, the advice given without judgment, and the countless small moments of connection he made seem effortless.
Rudolpho Valentino Degregorio leaves behind a legacy measured not in years, but in lives touched. He will be deeply missed by his family, friends, colleagues, and the many patrons who were fortunate enough to know him.
He is survived by his wife, Ellen, and his two children, Mickey and Daisy.
It was hard for me to explain the tears on my face to my wife as I read this over a couple of times. She asked if we’d become friends over the time I worked for him and I said, simply, no. Maybe it was a coincidence I met Rudy as my life was changing and I was coming to know the world. But I don’t think so. He was a mentor to me without either of us knowing it. He did all the wrong things for all the right reasons. I like to think he wanted to be good but nobody ever really showed him how, so he cobbled together bits and pieces he’d gathered and tried to figure it out. I was glad to see he’d had a life after the Inn and it sounded like some real good came from the things he tried to do. Maybe that’s all any of us can ever really ask.
