Bob Goes to Jail

When I looked up there were eight to ten guys with DEA flack jackets streaming into the lobby with more artillery than you’ve ever seen in your life and it just looked too real. My mind slowed everything down. I was confused. At first I thought: This is Jordan’s birthday. This is Jordan’s birthday and these are friends of Jordan’s that I don‘t know…

And then I thought: No. This is a joke. This is a joke and these are friends of Jordan’s that I don’t know… even though I know all of Jordan’s friends…

…and then I was spun around and I saw myself in the lobby mirror with one of those cylinder machine guns at the base of my brain stem and then another gun at my side and one to the middle of my back. They swung me around and one guy was pistol-whipping Jordan on the ground and they dragged me to the elevator.

At the elevator there was a very prominent sign that said:


So all eight of us got on.

It stalled.

One of the guys brought out one of those huge hammers that belonged on an anvil and started hammering the side of the elevator like a moron. I said “I can get the car moving again,” and they said, “Okay, but you better not do anything stupid.” Now, what the fuck was I going to do? I had three guns on me and I was cuffed. What am I, Bruce Lee?

I placed my foot on the sliding door of the elevator and pushed it open, and that reactivated the elevator and we were on our way up. I told the guys about Tybalt, my dog, (the love of my life, the reason I get out of bed in the morning, hung over or not, more likely hung over). They said that if he did anything they would have to shoot him.

Then, one of the guys (named Andy, I would find out later) said, “Look, I got dogs, I know how you feel. I’ll let you in the apartment first. If you can settle him down and if he seems okay, we won’t shoot him.”

What the fuck?

But we opened the door and I spoke to him and loved him and he was fine.

In fact, Tybalt was all happy and gleeful the way he usually was when a load came in: jumping up and down, running back and forth, cocktails anyone?

I knew these guys were some kind of Cowboy Superhero Cops, but as we entered the apartment the first words out of anybody’s mouth was not “Miranda” but “Where’s the cash? Where’s the cash?” There was no Miranda Warning until we were well into the apartment. There was our one load, a refrigerator box filled with dope, standing sentinel in the dining room like an upright coffin. And there were all the other accouterments: Hefty trash bags to be filled to 20lbs each; Bounce to offset the scent; duffel bags from the now sadly defunct Morris Brothers (a neighborhood store from across the street that had been around since before NBC had a color peacock), which would later be filled with pot to sell to other drug dealers; and a scale.

The TV was on in the living room, the Knicks playing the Larry Bird Celtics, and one of the guys started doing dips on an exercise bar I’d set up there.

Ralph Scott, the bad black cop, asked me where the cash was. I said I didn’t know.

He indicated the 250lb refrigerator box filled with pot and asked me if that was for personal use.

I said no.

He asked what the Bounce was for. And I told him.

He asked me what the trash bags were for. And I told him.

He asked me who Jordan was. I told him Jordan was in charge.

He indicated the jar of Vaseline on the table in front of me and suggested that I would need that in prison.  It dawned on me that Ralph wasn’t very nice. So I thought maybe I should stop answering his questions and talk to a lawyer. This time, we left the apartment in two shifts so we wouldn’t stall the elevator. Amazingly, leaving the building, we didn’t run into any other tenants. I gave the narc-y doorman a look because he always stared at me like I was up to something and I was sure he was the one who tipped off the DEA. (I understand that he is now dead.) On the way out, I twisted my body Houdini-style so my fingertips could creep out the apartment keys to give him so someone could take care of Tybalt.

Off we went downtown.

I looked outside the windows of the car; saw the Town Shop for Brassieres, Shakespeare and Co., Zabar’s, and people freely walking up and down the wide boulevards of Broadway, doing stuff. My inalienable right to wander around footloose and fancy-free just got snuffed: I was in the back of a cop car with my hands cuffed behind me, going downtown.

The agent driving me was nice. He said he had a feeling I would be okay, that things would turn out all right for me. Then we came to 57th and 12th, home of car dealerships and DEA headquarters. It was a shitty, almost deliberately depressing area of town.

Jordan was already there. We were processed, fingerprinted, photographed, and put in a cell together, both of us very weirded out.

Jordan asked me what I told them and I said not much: just that the boxes were to be distributed, the Bounce was there to cover the odor, the bags were to divvy the stuff up, that we used the scale to weigh stuff, and that he – Jordan – was in charge.

Jordan said that those were probably not good things to say.


I love Dad very much. He does the best he can. I suppose with all that old-line inbreeding, Sedgwicks are bound to have had a screw loose, or many screws loose, somewhere. We came from New England aristocracy. Some say, descendants of the Mayflower. Theodore Sedgwick, being the first to free a black slave in the US courts, beat Lincoln to the punch.

In Stockbridge, the sacred family stomping ground, there is a graveyard called the Sedgwick Pie. It’s called that because the Sedgwicks are all buried in concentric circles around the family patriarch, Judge Theodore Sedgwick, so that, come Judgment Day, when we all rise, each Sedgwick will see nothing other than other Sedgwicks.

It’s a long fall through the centuries to where I am now.

Our house in Croton-on-Hudson where we live from the mid to late 60’s is called “The Gingerbread House.” It is a real live Gingerbread House. There’s the white picket fence with the little sign that says “The Gingerbread House” in the most elegant fairy tale script you ever saw. And there’s the dell with a playhouse, the red clay tennis court, and the family dog, who is now whirling around my father and me. His name is Golden Boy.

He is sprinting around us like a racehorse and there is so much laughter I can’t breathe anymore and I am getting dizzy. We keep spinning around to look at him, this beautiful golden dog who is so proud and magical. He seems like he must have come from a land of fairy tales. But, then again, all dogs come from a land of fairy tales. My father is so young and happy in his new lumberjack jacket and he loves the dog so much and we love each other so much and the dog loves us both so much he can’t stop whirring around us at an almost blinding speed.

He will fly soon.

During the winter we freeze our asses off waiting at the top of the driveway for the bus to take us to our depressing school. From across the road (the mysterious side) wolves come down from their lairs down the steep mountainside to see what my brother and sister and I are up to and if anyone happens to be looking after us. Golden Boy trots across to the mysterious side of the road right into the middle of the pack, and I suppose they all just reason it out because the wolves always leave very peaceably and no one says anything.

Once Golden Boy bites into a live telephone wire after a storm and he should be dead. He is dead. My father throws him into the tiny Volkswagen convinced he’s dead. We all drive to the vet crying. Halfway there, in the rear view mirror, up pops Golden Boy, resurrected, panting, bleeding, happy to be going for a ride somewhere and thrilled to be the center of attention. When my father tells the telephone company about the incident, they say it isn’t possible for any living thing to absorb that much voltage. They’d be dead.

The Gingerbread House itself is flat-out Hansel and Gretel territory. The top half is exposed splintery wood. The bottom half is painted all white and covered with hand-painted hearts, flowers, roosters, sparrows. When you walk in the front, thick, airtight, blood red door, the smell hasn’t changed in 200 years: wood older than the Declaration of Independence, stake-sized rusted nails in half-moon warped floorboards, and mildew. You’re immediately thrown back to a cozier, more welcoming time: “Hello, and how are you?” Not like today, where everything smells like an airport and some person asks in a faraway voice, “Do you have a reservation?” Of course you don’t. You’ve failed. Go away.

The ceiling downstairs is so low that, at 6’4 & 1/2, my father perpetually has to duck. In the summer it gets broiling.

“Get your bathing suits on!” says Dad, running up the blood red staircase to the living room where my brother Nikko and I are watching TV. The face boards, like the outside of the house, have hand painted pictures of chickens, roosters, flowers, and phrases in French that I don’t understand.

“But Dad,” we whine, “It’s about to rain.”

“I know! That’s the whole idea!”

“But Daaaaad!”

“No whining! And put your sneakers on!”

We obey. We dress. We are as ready as we’re ever going to be. Dad is hopping like a child and is so happy and we lift up the old metal latch and open the airtight door and you have never seen such rain! Millions of gallons plopping down from a black sky. Dad skips out and starts laughing and shouting. Nikko and I start out dubiously, slinking, but we’re immediately drenched, so any fantasy of somehow keeping dry vanishes.

Dad is ecstasy unhinged, dancing, spinning, such a great idea he had about our sneakers because the pebbles underfoot in the driveway are painless.

We start laughing and yelling, because Dad is laughing and yelling. We start running up the driveway. What could be better than this? No one else is doing this, just us!

Golden Boy comes out of the woods from his own adventures to join ours. He is so red he looks like an Irish setter. He barks and jumps high up and laughs with us because he is so happy that we are all so happy, and the rain is just ridiculous it’s pelting so hard – but it now feels like some giant massage, and we all four must look so silly because we’re all just jumping up and down and running and laughing uncontrollably and doing these weird movements to some odd music no one else is hearing.

We are all so in love with everything.

At the top of the driveway, Dad turns right, so we all turn to follow, I don’t think our feet are touching the ground, Golden Boy running brilliant, extended, effortless, Dad a little ahead of us.

A car stops next to him; the driver wants to tell him something. Dad and the head sticking out of the car confer. The car leaves.

Dad comes up to us and says that the guy in the car said: “You all look like you’re having more fun than anyone else in the world.”


Jordan and I got our phone calls. I called my brother, Nikko, because I figured he’d be home. He answered. “Hello.”

“Hi Nikko, it’s your brother, Rob.”

“Hi, brother Rob. It’s your brother, Nikko.” He sounds as usual, like an above-it-all asshole. He always did this and it always annoyed me. He was not grasping the severity of the situation.

“Okay. Write this down. Have Mom and Ben” – my all-powerful, art-dealing stepfather – “come down to 40 Foley Square at noon.”

I heard him mumbling as if he were doing an assignment for class. “Hold on, hold on.” He stopped. “Are you in jail?”

“Yes!” I was glad I was able to stick it to him, that my plight was a serious one, impressive, and that he would have to drop his obnoxious tone for a change.

“Is Jordan–”

He was going to ask, “Is Jordan there?” Knowing the phone was probably tapped, acting the experienced pro, I hung up the phone before he could get the word out. It was a very slick move on my part. I was confident that it would throw the DEA off the track.


All this because one pleasant fall evening in 1988, while walking Tybalt, I saw Jordan talking on a pay phone.

At 6’5” and 190lbs, his body shaped like a question mark, Jordan looked like Ichabod Crane. I’d always disapproved of him and felt superior: he was a drug dealer while I merely consumed them. But, on that particular night, I yearned for a connection to someone so I could feel good about myself. Work was not good; money was bad. I had asked my grandfather, who was off to the West Indies for his annual midwinter retreat with my grandmother, if I could stay in his huge Upper West Side apartment while they were away.

He said yes.

So, that’s where Jordan was, right in front of my grandparent’s snazzy old-world apartment building on 85th and Broadway, talking out of the side of his mouth on a greasy pay phone about God knows what. Whatever it was I got the distinct impression he was up to no good.

On that night, however, I was lonely enough that I just wanted to make nice with Jordan. I needed companionship. He was best friends with my brother Nikko. I wanted to exude loyalty. Once I made nice, we could hang out at parties. It would be fun.

When he hung up the phone I asked, “Are you doing nudge, nudge, wink, wink?”

He said yes, that he had a “load” up the street in some house with a bunch of schvartzes. So I asked if he wanted to come upstairs and use the phone.

He said yes.

After he was done mumbling his phone calls, pretending not to hear them, I offered him this:

“Any time you’re in the neighborhood, doing whatever it is that you do, I insist you come up here and use my phone.” Here was my opportunity to be magnanimous, to be the big man. To be liked. To be well liked.




“In fact I insist that you use this apartment for whatever contraband you have. For all your needs.”



After a quick tour of the twelve-room apartment, (he cased the joint! I’d always wanted to use “case the joint” in a sentence!) he came back to the kitchen and said, “You know, this could really work out.”

“I insist it work out,” I said, with an exalted flourish of my hand.

“And you would be paid.”

“Nonsense. How much?”

I was within a cunt-hair of food stamps.

“A lot.”

“What’s a lot?”

“Three grand a pop and I do two loads a month. So that’s $70 grand a year for sitting around with your thumb up your ass.”

“No shit?” I said with my thumb up my ass.

And on that day, God created The Moron.

10 Comments on Bob Goes to Jail

  1. I just read your excerpt in the N Y Times mag and was compelled to check out your story. Good Luck . . . I like your writing style.

  2. Not only is it a funny and compelling read but I can already imagine it as a great Hollywood movie. I especially loved the description of the DEA agents interactions with you “what is the bounce used for?’ and that the drug dealer is using old yiddishisms like schvartze. It has the ring of a bestseller can’t wait to buy my copy and read from end to end.

  3. “I was within a cunt-hair of food stamps.” Sorry, but your writing sucks. I empathize with your story’s particular horror, and have lost a sibling (lesbian female) to a similar, DEA-related raid. But why a gender-specific hair, and the negative tone? Please take care not to alienate your female readers.

  4. You invoked Morris Brothers. What are you doing in this picture? You look like you have hives. Nice work. When can I read the whole thing?

  5. Compelling excerpts that paint vivid images through the deft use of language. I am eagerly awaiting the release of the complete book.

  6. I’ve been a friend of Rob’s for many years, but he never told
    the story to me. I am captivated and interested to read on.

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