Being a Pinkerton
- swbutcher

- Jul 11, 2021
- 9 min read

Pinkerton image off internet)
July 1985
Ted and I stand at the front desk of the Pinkerton Security offices. We are on the second floor of an old wooden building beneath one end of the grandstands at the Saratoga Race Course. We are going to be part of the Saratoga horse racing experience, part of what everyone talks about when they think of Saratoga in August. We are going to be a part of the long horse racing history that started in 1863 at one of the oldest racetracks in the country, part of the Travers Stakes and so many other Grade I thoroughbred stakes that race at the nine-furlong flat track. We are going to be Pinkerton security guards and be right in the middle of the whole scene, tasked with protecting dignitaries, celebrities, jockeys, and making sure the whole operation runs smoothly.
A tall, imposing sergeant stands before us on the opposite side of a wooden counter. He looks every bit a veteran of security and law enforcement, with wide shoulders covered by a dark blue short-sleeved button-down shirt, a gold Pinkerton badge on his right breast, an American flag patch on the right shoulder, and a Pinkerton patch on the left. He wears slate-grey uniform pants and a utility belt with a sidearm, cuffs and ammunition. He is a Pinkerton. I am going to be a Pinkerton too.
“Hello, we heard that you might be hiring for security work?”
The sergeant looks us over. I suddenly feel ridiculous in my sneakers, shorts and tee shirt, but it’s what I had on when we drove into town. The sergeant pushes two pieces of paper across the desk toward us and tosses two pencils on top of the forms.
“Fill this out,” he says.
The forms are brief, not much more than name and address, not what I expected from this elite security institution.
The sergeant eyes Ted.
“What’s your waist?”
“Thirty,” Ted says.
The sergeant turns to a rack of pants and pulls a pair off a hanger. He grabs a uniform shirt off a different rack and a hat from a stack, and hands the three items to Ted.
The sergeant turns to me.
“Thirty one,” I say.
The sergeant grabs another set of clothes that make up a uniform, and hands them to me.
“Thirty-four is the closest I have. Take them to Tony on Caroline Street. He’ll take them in for you for two bucks. Turns them around in a day. Be here tomorrow morning at nine, sharp.“
“Yes sir,” we say in unison.
“Thirty-two dollars a day. Nine to five. Do you carry a gun?”
“A gun?” I ask.
“Thirty-seven bucks if you have a license and you supply the sidearm.”
“No, I do not have a gun.”
An aside. A few days later, I cross paths with a kid who took the sergeant up on the five-dollar side-arm bonus. He is short and skinny, probably five-foot-three or -four and maybe 120 pounds in a soaking wet uniform. His pants and shirt are baggy on his small frame. But what makes him memorable is the gun he carries, a .357 Magnum straight out of the Clint Eastwood movies. The barrel is as long as the kid’s femur. He and three other armed Pinkertons escort cashiers from one clubhouse to another. I see them coming toward me from across a yard, three big men who look the part and one kid who looks like the goober who sells tickets to the movies in Fast Times at Ridgemont High. I wonder if, when the need arises, he will be able to lift the pistol and whether the kick from firing it will knock him on his ass.
“OK, then,” the sergeant says, “thirty-two dollars a day.”
And that is that. We are officially Pinkertons. We are part of the scene.
The next morning, some of the Pinkerton shine has begun to wear off. Tony, true to his billing, did a fast job of alteration but in his haste he altered the pants from a thirty-four, not to a thirty-one, but to a twenty-nine inch waist. The result is not just that the pants are tight and uncomfortable but that in making such a drastic change in waist size, Tony had to sew the rear of the pants so much that the two back pockets have the appearance of being one large pocket that spans the width of my backside. Worse, in creating this one, ass-spanning pocket, he has rendered both pockets useless and has sewn them shut. Ted finds this tailoring very funny and immediately gives me a nickname I bear for the summer: “Pockets.” The Pinkerton shine wears off further when, while walking to our first post, another new recruit turns to me and says, “So, this is what it’s like to be the lowest form of rent-a-cop.”
Later in the day, a sergeant leads me to a locked door beneath the grandstands and through a maze of stairways and narrow hallways. We turn right, then left, then right again, finally arriving at a door that he holds open for me. I enter the space to see a long row of tellers, their backs to me. Without pausing, the sergeant leads me to the opposite end of the tellers and stops at the threshold of a small room.
“The guy who is usually here is on break. You stay right here until he returns.” The sergeant points to a metal stool, tall, like a barstool.
“That is the vault. No one goes into or out of the vault unless they show you ID. Got it?” ‘Got it’ is not a question. I lean across the threshold of the vault and sure enough, there are stacks of money on desks. A few people counting, sorting, scribbling stuff on paper. Behind them are more tables and more money.
“You do not go in the vault. You stay right here.”
“So, you want me to sit on this stool and guard the vault. No one enters or leaves unless they show me ID, right?”
“Until the regular guy gets back from lunch.”
With that, the sergeant heads off, down the narrow space behind the tellers, without saying another word.
I climb onto the stool and look around. I am guarding the vault. To my right are the tellers, probably twenty of them. They sit with a cash drawer in front of them and some sort of keypad slightly off to the side. Through a small window they take bets on the races. On the other side of a plastic half-window I hear voices ranging from the tentative “I’d like to bet two dollars on the number one horse, Lucky Day, to win in the fifth race” to the rapid-fire experienced betters, “Twenty on a two-five quinella in the fifth.” The tellers repeat the bets to the customers and take their money before hitting a key that prints a receipt, and offer their unenthusiastic support: “Good luck.”
I look up at the wall that separates the tellers from the masses. It’s wood-framed, finished on the side facing the public but unfinished before the tellers. I see one-inch plywood nailed to two-by-fours. The wall is probably eight feet tall. A wire screen extends another two or three feet, and above that is open air for five or so feet before you get to the bottom of the grandstands.
To my left is the vault, which appears to be a big room with desks, tables, and lots of money. I lean forward but cannot see the big steel door that I think of as securing a vault. It all seems so casual. I turn back to the tellers and the wall separating them from the public and wonder: if I were a thief, how would I rob this place? I figure that a small group of even moderately athletic individuals could, with a running start, probably scale and clear the wooden wall topped with metal fence fairly easily. Unless one of these tellers is armed, once the robbers got behind the wall they would have quick access to the vault, and it would just be a matter of grabbing as much money as they could and running before the cavalry arrives. If these thieves had guns, there would probably be some sort of shootout but I imagine a well-planned and executed heist would be pretty easy.
I wonder what my role in the whole thing would be. What would I do if I heard the scream of a teller and saw five, three, or even one armed thief hurdling the wall? Me, in my blue and grey Pinkerton uniform complete with a single pants pocket, straw hat and tin badge. My mind goes to the line from a Tom Petty song “Yeah I got a permit, to wear this .38 but listen my life’s worth more than minimum wage.” Yeah. I’d probably step aside. Might not even ask for ID.
Later, after being relieved from my vault post, I help with the crowd control. I stand at my post, keeping an eye on the betting windows. My back is to the track and every thirty or so minutes there is a rush of people from the windows to the track where I hear the horses thunder past, the roar of a crowd, and then a rush from the track back to the windows as people place bets on the next race or cash in their winning ticket. To my right I see Ted forty or so feet away at a similar post, watching the teller windows, eating a bologna and cheese sandwich on white bread. A few days ago he told me that one of the girls working concessions, she might be in 8th grade, told him she had a crush on him. Since then she’d made him sandwiches every day and brought them to work so he wouldn’t be hungry. He thinks the whole thing is odd and hysterical but a sandwich is a sandwich. Ted turns to me mid-bite and gives me a nod. I curse him under my breath.
I turn back to the windows to see a woman, probably in her thirties, standing directly in front of me. With my acute Pinkerton security sense I determine that she is probably into her fourth or maybe fifth Saratoga Sunrise and it is barely noon. She works to focus pushing her glasses up onto her nose. She is several inches shorter than me, so as the glasses fall she scrunches her nose and lifts her upper lip. This results in a half-open mouth that expels fumes of cheap vodka and fruit juice. As she’s standing directly in front of me, uncomfortably close, I do my best with small talk.
“Nice day,” I say. “You picking winners?”
“Oh, I just like watching the horses and the people.”
“Do you come to the races often?”
“We come a couple times in the summer.”
Her daughter, maybe five, stands beside her, close enough to me that she too has to crane her neck and scrunch her nose to lift her glasses so she can see me clearly. The daughter is the spitting image of her mother, right down to the glasses but minus the concerted effort to maintain balance.
“I live out by Saratoga Lake,” the mother says. “You get out to the lake? You should come by some afternoon to… you know.”
She lets the words hang there. I say nothing. I look at her, confused, hoping that I’ve misunderstood. She sways before me and I pray she does not reach to me for stability. I turn to the daughter, who is still scrunching her nose. The daughter reaches for her mother’s hand but that hand is occupied, holding a plastic cup.
From behind the woman a man approaches from the teller windows holding a couple betting slip. He’s got soft features and wears a white t-shirt that doesn’t quite reach over his protruding stomach to his pants. A few inches of pale pink flesh. He stands beside the woman. Now there are three of them standing well into my personal space. My mind flashes to all the ways this whole scene is wrong.
“I hope you enjoy the races,” I say. “I have to check in with my supervisor.” With that I find Ted to ask how he enjoyed his lunch.
Some days are more exciting than others. There is a moment of panic, like when a sergeant and I are rushing a woman to an ambulance after she passed out due to the heat. We have her lying face up on a gurney with an oxygen mask over her mouth, and are taking the freight elevator to the ground floor, except that the elevator door on the ground floor is locked and when we arrive all we see is the faces of two ambulance attendants and a couple of Pinkertons struggling trying to lift a locked metal gate. As the sergeant pounds elevator buttons to get us to another floor, the woman starts to vomit in her mask. I remove the mask and roll her on her side so she can vomit on the floor. By the time we get out of the elevator, the woman is conscious and probably could walk back to the grandstands on her own.
There are moments of hilarity like when a little girl, at the request of her mother, asks me to talk to a group of bikers. “My mothers says she thinks she smells… marijuana.” ‘Hang on,’ I think, ‘better call backup.’
But most days are much less eventful, a lot of standing around in the heat and watching people. Most days end with Ted and me walking back to the one-room unfurnished apartment that we’d sublet for the month, Ted talking about the lunch his middle-school admirer made him and me complaining about how the too-tight pants are giving me a rash.



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