What Makes Sammy Run? A Trading Assistant Races Up Wall Street

TC was a hedge fund equities trader when he got a cold call from an impetuous sell-side trading assistant. Sammy would cross TC’s path for the next ten years.

Around 2005 my crew really started hitting our stride on Wall Street. Said differently, the whole lot of us were finally making proper money. Money may not be the most important thing in the world. Sometimes it comes with its own problems. There may be diminishing returns to wealth once you have enough in your pocket to live well. But a million little nightmares, that might otherwise trip you up, simply disappear when you earn six figures.

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This was the frame of mind I was in when the outside phone line rang. It was unusual for our personal lines to ring on the trading desk. After all I had a turret, a telephone system with direct lines to 60 sales traders at broker-dealers. And there was a separate method for my fund’s portfolio managers to reach me to fix something for them or trade. Why would I want to take an outside phone call? That’s stupid.

I banged off a couple of orders, finished up an instant message, picked up the line, and heard the voice of someone who was to cross my path over the next ten years. Let’s call him Sammy. An avalanche of certitude came through the receiver.

“Hey! About time you picked up, I was just about to hang up on you and then you would’ve missed a real opportunity. I’m calling from Bernstein, we’re a buyer of Motorola on the desk and I saw your sales coverage is on the phone and I didn’t know if he was calling you or not. But I know you’re interested in the name and we have to buy it in size, like a major account, we have a motivated-buyer. We could take you out of your position because I saw your 13F and we’ll trade half of it on the offer. Why don’t you check around internally and ask if they want to sell the whole thing? I’m right here, I’ll wait, go ahead and make the call…

“Well, whaddya-wanna-do?”

Sammy had just broken about 500 rules on Wall Street. You didn’t just call up a buy-side client like us and talk to a trader that way. Especially if you’re a lowly assistant sales trader, as I was sure he was. I am in awe at the magnitude of his bluster.

I gather myself together and say to him, “You like your job, Sammy? Because you’re not going to have it very long - tell your boss to call me.”

And then I hung up the phone. I wasn’t really going to rat him out, I just don’t have time for cold calls. I get “IOIs” (indications of interest) over Autex and Bloomberg. Cold calling an offer like Sammy had done was just a waste of everyone’s time.

Half a second later the phone rings again. “Hey, it’s Sammy… sounds like we got disconnected. But you asked me a question and the answer is I do like my job. This year. But if I have it next year, it’ll stink.”

He sounded so tense and serious I almost laughed in his face. I liked him. As a rule, the trouble with Wall Street is that too many people who won’t leave are ashamed to be there. I didn’t get the feeling Sammy was ashamed at all. I say to him, “I’ll keep my ear to the ground for you kid, maybe in a couple of years you’ll have a chance to back up the salesperson on my account.”

What followed was the first time he ever scared me. Here I was going out of my way to be nice to him and he answered me with a tone that was almost contemptuous. “Thanks” he said, “but don’t do me any favors. I know this Wall Street racket. Couple of years as an assistant sales trader? So I make fifty grand. Then a stretch covering hedge funds? One-fifty. And finally you’re a big shot sales trader and get three hundred for the rest of your life. No, thanks”

I just held the phone limply, staggered. Then… “Hey boy! Over here, on the hop!” And he just dashed off, didn’t even bother to hang up the phone on me. Well, I guess he knew what he was doing. The world was a race to Sammy. He was running against time.

Sammy could be composed in the manner of all fictional characters, out of a writer’s recognition of similar and overlapping traits in various individuals who have passed within his circle of observation. But Sammy is real. He’s as real as you and me are right now. Even if we went months without speaking, I could hear Sammy crowing around Wall Street like a bantam cock.

The second time Sammy and I spoke was in person. He turned up at a big event thrown by the Robin Hood Foundation. Robin Hood’s mission is to fight poverty in New York City, but no one at the event gave a shit about that, because the evenings were loaded with celebrities, all mixing with the biggest names on Wall Street. John Griffin’s laughing with Jon Stewart. Lee Ainslee talking up the Giants defense to Tom Brady. David Einhorn trading healthcare picks with Martha Stewart. Alan Schwartz and Larry Robbins yucking it up with Aerosmith. Ken Langone drinking bourbon with folk rock legend Graham Nash.

A fundraiser on a boat may be more fun, but there was nothing like the Robin Hood events and there never will be again. I’d have bought a ticket to just stand there watching people watch each other.

Sammy had been promoted to sales trader. He swaggers in, meets my eye and blurts out, “Hey shake hands with God’s gift to Wall Street” while grabbing my hand before I had a chance to pull it away. He immediately launched into one joke after another and I laughed my ass off the rest of the night. Finally, someone in finance who didn’t see dark clouds behind every silver lining.

Just one thing rankled me about Sammy. Whenever he saw someone more important than us, which was often, he’d just break off mid-sentence and go introduce himself to them. At the time I shrugged it off as America; all the glory and the opportunity, the push and the speed, the grinding of gears and the crap.

Besides, no one else seemed to mind; Sammy always had the ability to do everything just well enough not to break his stride. He had a colossal lack of perspective. In 2007 this was a valuable gift, because perspective doesn’t always pay, it mostly slows you down and makes you unhappy. And there was money to be made after all.

As I left Robin Hood for a new afterhours place called The Box, I looked back and saw Sammy entertaining a group of the most important people in New York. He’d made his way into the center of the room, the focus of attention at a table where you can’t even buy a seat; strictly invite-only. He finishes his story with a dramatic two-handed jerking-off gesture at eye level, while gaping with his mouth open like an amateur porn star. Then he and Matt Lauer dissolve into laughter with their arms around each other.

The third time we met was at The Campbell. The Campbell was a beautiful bar in Grand Central Terminal. When you walked in you felt like you had been transported to an upscale speakeasy in the 1920s. Even though I didn’t commute, it’s wonderful what that scene and a few fingers of scotch will do on an empty brain. Sammy had called me up on my outside line again and wanted to meet. When we did, he wore a new expression that I disliked even more than the last one.

Back then you made your reputation on Wall Street by how much money you could publicly throw away. And good god, could Sammy throw it away. This was in the middle of the financial crisis, so even though he wasn’t the sales trader on our account, we must’ve talked about business. I remember people were afraid to trade through Morgan Stanley that Friday, thinking there was a run on them and their trades would not clear. I think their stock was $8 at the time. It was dramatic stuff and Sammy was making the case that Bernstein was a solid alternative to Morgan, being backed by the asset management business and parent company Alliance. I could hardly disagree, but the night was a complete bender and I can’t say what else I may have conceded that evening.

A week later my sales trader at Bernstein calls me up and says that he appreciated the opportunity to cover my account and that while he understood why I wanted Sammy to take over, he hoped we could stay friends.

Sammy had spent his time wisely since Robin Hood. He decided what accounts he wanted to steal from his colleagues and made a move on all of them. He knifed his fellow man in the back with such gusto and brilliance that it fascinated me as a tour de force. He was so conscientious about being unscrupulous that you almost had to admire him. But I could read him like the top line of an optometrist’s chart and I wasn’t having any of it. I tell my guy he’s still on the account, I’m not changing coverage, and to put his boss on.

Now I feel like I’ve used my position on Wall Street responsibly. I’ve rarely gone out of my way to hurt someone, but this situation called for all the sensitivity of a slaughterhouse worker slitting a steer’s throat. Sammy had to be stopped. Someone had to draw the line.

Todd, Bernstein’s then-head of sales and trading calls me back and I launch into him. How dare he just swap out the trader covering me without talking to me first, I decided who was covering my account, not him and certainly not that little twerp Sammy. Todd’s a little taken aback. He says Sammy told him we’d discussed the matter over drinks. He knew Sammy was one of my best friends and everyone figured it would mean more business for the firm if he covered the account.

I recovered a modicum of tact and realized I couldn’t recall much of the night out last week or whenever it was. Bernstein had a reputation as the good guys on the Street. Perhaps I was overreacting. I was under pressure at work and when you’re down the most trivial slight becomes persecution. But then I catch myself; if Sammy really believed we were friends, he shouldn’t be leveraging that friendship at work.

Sammy is taken off the account. His scheming becomes more transparent. It’s a setback for him with senior executives. The other sales traders are more wary. However, Sammy was built like a boomerang; the harder you throw him out the faster he comes back.

I didn’t hear from Sammy after that. Through the grapevine I gathered his career continued its meteoric rise. True to his word, he soon left the trading desk. Moved into sales. Then investment banking; mergers and acquisitions. The rewards for someone in murders and executions were unlimited, perfect for someone who believes going through life with a conscience is like driving a car with the hand brake on.

I’d often find my gaze wandering to my outside line though. Wondering when he was going to call again. Skip forward a couple more years and I was still riding high. My fund had navigated the financial crisis admirably and I was blissfully unaware I had a target on my back.

Broker-dealers were constantly trying to get me out to dinners and entertainment, but I was starting a family and had become more discerning about who I spent time with. Certainly where I spent my time. That said, one sure way to get me out was for the opening of a new restaurant. And that’s how I found myself at the opening of The Dutch down on Sullivan.

It’s one of the hottest tickets in town. I walk in and Sammy is there, holding court. He’s the same guy, all smiles and confidence and enthusiasm. Perhaps he’s put on a little weight, but that’s mostly offset by the cut of an expensive suit. There was something savage and tense about the group with him. They’re sharks. Ruthless. Predators at the top of the financial food chain.

But I seem to notice a momentary crack in his demeanor when he sees me. He extended his hand like he expected me to crack it with a ruler. I could feel the perspiration in his palm. As if he’d swallowed his pride, but it stuck in his throat like a fish bone.

But it’s just that - a moment. In no time he recovers. Regains his composure, tells me he doesn’t care a whit about sales trading or a second-tier firm like Bernstein. Nor me for that matter - he has more important people to hate. I tell him I’m married now and he says I’m on a fool’s errand; that if you chase after women you will run out of money, but if you chase after money you will never run out of women. Everyone laughs and just like that he’s back on top. Like a whistle sounded, the signal for him to forget about my previous slight and go about his business again.

The Dutch was a great restaurant, but with Sammy there it had all the intimacy of Madison Square Garden. Something had changed for the better with us though - we knew where the other stood now. I took him for what he was, not what I expected him to be. For his part, he just wasn’t that interested in business with my hedge fund. Our antipathy towards each other became a bond. As our colleagues departed, we found ourselves sitting together again and recalling our evening out during the financial crisis. He told me how nervous he was to cold call me a second time, how he misjudged our conversation and how bad he felt about it afterwards. There was a vulnerability that comes from seeing yourself in someone else.

Around 2am, the two of us are nursing drinks while the staff cleans up around us. We’d been drinking all night but somehow felt sharp and sober, reflecting the give and take of a meaningful conversation. As we say our goodbyes, we make heartfelt promises that have no chance of being fulfilled.

A year later I found myself dismissed from my position on the trading desk and rightly so. The job had changed and I refused to change with it. My firm was gracious enough to allow me to work out the rest of the year at my station. You couldn’t ask for more than that. I put my head down at the office and took every meeting I could outside of it.

If you find yourself suddenly unemployed, it’s useful to know that every meeting is an interview anyway. So just get the meeting, the rest will take care of itself. The easiest way to do that is simply to ask people for advice; 99% of people will be flattered by that approach and the other 1% weren’t going to help you anyway - screw those guys.

Unconsciously I had already made a career out of meeting with anyone, no matter how unimportant, so this part of my job search came easily. But inevitably, I found my eyes drawn to the outside line. Surely Sammy had heard I had been fired? I’d spoken to other people at his firm. They must’ve told him. He was so switched on and plugged into Wall Street. Why didn’t he call?

Looking for a new job is like being on a desert island to some extent - waiting for a message in a bottle. Nowadays I don’t take it personally; if you’re out of sight you’re out of mind. It’s just business. It is almost Christmas when Sammy finally contacts me. We’ve been playing a game of chicken and he has waited until my last week in the office before reaching out.

I marvel at how different the call is from the first time we spoke. For a start his assistant connects us, then after an arguably inappropriate length of time on hold, he launches into the conversation with a patrician’s air. Says he had just heard I had decided to move on to greener pastures and he’d be interested in hearing my plans. And of course, perhaps he could be of assistance. He is going to be out east. He’s sure I will be out there soon as well, after all no one spends New Year’s in the city anymore. Why don’t I drop by and see him? His assistant will follow up with his address and a time that works.

And in the new year, that’s where I found myself. I plugged his address into my Garmin GPS and made the pilgrimage out to Amagansett, Long Island. I drive through the gates towards his house and Sammy meets me at the top step. He has that old twinkle in his eye. Says, “Well? You finally came to kiss the ring?”

And thank God I already have a job offer in hand. Because that day would’ve been unbearable otherwise. Yes, Sammy would’ve helped me. A man in his position can move mountains. But I would pay. Pay one way or another. A week prior, I would have climbed a mountain of broken glass to get to him; barefoot, uphill both ways.

Instead, I casually inform him I have moved to a family office. That yes, I’m a partner now. I begin to tell him some more details, but he’s not interested; his quarry escaped him. But then we fall back into our previous friendship. Recall the good times at trading conferences in Savannah, golf outings at Winged Foot, fundraisers at the Intrepid, restaurant openings in Midtown. For an hour we reminisce, the sort of animated conversation where you forget to refill your drinks, interrupt each other with minute details, and enrich the stories meaningfully in so many other ways.

Eventually, we fall back into a contented silence. But it doesn’t last; Sammy being Sammy, he tries to break it with a joke. He had every material possession, but didn’t seem to know what to do with himself when he wasn’t talking.

Perhaps life is a choice between being a nice guy and a flop, or the way Sammy is now. But I don’t think he even had that choice. The world decided it for him. As I drove off, I saw him standing outside on his palatial steps, under the giant American oaks, looking out over his hundreds of yards of landscaping that terraced down to the wall that surrounded his property. Sammy was a lonely figure in the shadow of millions, the terrible little conqueror, the poor little guy, staring after my car as it drove out the main gates, waiting for the next guest to kiss the ring or perhaps bring some laughter.

I drove back slowly, heavy with the exhaustion I always felt after being with Sammy too long. I thought of him wandering alone through all his brightly lit rooms. Not only tonight, but all the nights of his life. And I looked ahead to the warm comfort of my family and my rented apartment.

TC is the pseudonym of a buy-side equities trader who produces the “autobiographical novel” podcast “Occupy a Job on Wall Street.” Many of his finance and New York City stories take place in the 2000-aughts, a time he claims was “when my business and New York City were fun.” But he also admits that when people complain that times used to be fun, they really mean they used to be young. TC’s website is here and his podcast is available on  Amazon, Apple, Soundcloud, and Spotify.

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