Tenderloin San Francisco

Hard-boiled stories from San Francisco's 1960s and 1970s Tenderloin

Tenderloin San Francisco

Hard-boiled stories from San Francisco's 1960s and 1970s Tenderloin

A Memorable Experience



     Tripper Bob woke up, groaned, put the coffee on, and sat there staring out the window at a brick wall across the alley enjoying the view from his $1.50 a night room.  He thought about his recent fall from respected professional gunman down to a flea-infested room, a few bucks in his pocket, no prospects, and a $50 a day habit.  A few minutes later he poured himself a cup of hot black coffee and sat down to breakfast – half a roll of bennies and a vitamin pill.  While sipping his coffee he carefully cooked up his last balloon of smack, shot it, and nodded out.  Ten minutes after that the bennies kicked in and he suddenly sat up.  He double checked his .32 semi-auto, got dressed, put on his long black leather coat, sunglasses, and hit the streets.  It was dark and the night crew in the Tenderloin would be out soon.  San Francisco’s Tenderloin is an area of about thirty blocks which is known as a dangerous anything-goes inner city.  This was Tripper Bob’s turf . . .

     Bob hadn't eaten in a few days so he hoofed it to Compton’s to try to hold down a meal.  Compton’s was a 24 hour cafeteria in the Tenderloin which served cheap meals without a time limit – a coffee could last for hours, a meal could last all night.  Compton’s served as a gathering place to hang out, make connections, or simply gossip.  Tripper Bob was in a desperate situation and needed a big score to get back on his feet.  He knew by later tonight he’d be so dopesick he wouldn't be able to function.  His luck needed to change, and fast.  Compton’s was a good place to kill some time waiting for the clubs to get going and sometimes information he could use passed through there.  

     Tripper Bob got his meal, sat down, and tried to eat.  He kept his eyes on the door looking for some action when Eddie the Flash came in.  He might have something he could give Bob a lead on.  Eddie knew everyone and everyone liked Eddie.  He had a Polaroid Instant camera – made the rounds to all the clubs – took pictures of the queens and trannies with their sailor boyfriends for a buck – put them in a nice little display folder for another buck.  Because he got around so much and knew everyone Eddie heard a lot.  He didn’t talk much unless he knew you well and you showed your appreciation.  Tonight Bob couldn’t show much appreciation - he was down to his last two bucks.

     Eddie came over to Bob wearing his permanent smile, “Hi’ya Bob, good to see ya.”  Eddie didn’t really care if you were dead or alive, this was his image – a guy with the Polaroid who was happy to see everyone.  As with most everything else in this world it was a complete lie.

     Bob: “Hey Eddie anything going on I should know about?”

     Seeing Bob didn’t look too good Eddie turned to leave but still smiling, “Naw, nothing much going on . . .” he trailed off while hurrying towards the door.  Eddie knew if you were eating in Compton’s and looking sick you were flat broke.  To soften his exit yet keep on good terms with Bob, Eddie finished with, “But I’ll keep my ears open for you – if I hear anything I’ll let you know.”  Translation: no money, no info, but we’re still on good terms.  People wanted to be on good terms with Tripper Bob – he was a gunman with a reputation.

     Bob didn’t try to put the touch on Eddie for a few bucks, or push him for any news.  Hardcore street junkie though he was, Bob had some sort of ethics where he didn’t ask, or beg for favors.  He would take, rip off, set up, or shoot when necessary, but not ask.  The word ‘please’ didn’t exist in his vocabulary.  In that regard he didn’t fit the usual description of a long-time user.  

     Finishing about half of his meal knowing that's all he could hold down, Bob left Compton’s heading towards The Trapp, a well-known Tenderloin bar.  He hoped to find Gary there.  He did.  Big, tough, and good-looking, Gary was a regular in The Trapp.  It was known he’d hire out to do anything.  Gary and Bob were friends as much as any two bad-ass junkies can be.  No ‘hello’s,’ or ‘how’ya doin’s’ or anything like that – they knew each other too well.  Bob just started in, “Hey Gary – look I’m gonna be in trouble in a while.  I need some quick action. Know of anything going on?  I’ll cut you a piece.”

     “Oh, yeah, hi’ya Bob.  Naw, too early.  Haven’t heard anything.  Couple punks gonna do a few liquor stores down the coast - I don’t think you want that.  But I mean if you do . . .”

     Annoyed, Bob interrupted, “Gary, man, if I want a goddamn liquor store, I’ll do my own.”  And continuing with a little muscle in his voice, “Now c’mon, I’m not fuckin’ around.  I’m going to need something soon.”  

     Gary stiffening up enough to push back on Tripper Bob a little, “Yeah well that’s all I got.  Go to Kenny’s tonight, might be some action, might be some money.  I’ll be there early.  If I hear anything I’ll let you know.”

     Bob mumbled, “Yeah, yeah,” shaking his head as he went out the door, turning right and slowly walking up Eddy.  The bennies began wearing off.  He still had a half roll, but wanted to hang onto it as a last resort.  He thought, “Fuck, I gotta kill another hour - I’ll go back to Compton’s with my last buck till Kenny’s opens . . .”  

     Kenny’s Upstairs was right in the heart of the Tenderloin, 292 Turk street, second floor.  It officially opened at 2 AM and closed at 6 AM.  One dollar got an Irish coffee which had some decent booze in it.  Two beat cops came in regularly, collected their $100, then left.  They never saw anything wrong there.  Kenny’s was a hot spot for the sailors and every queen, hustler, straight, working girl, and anyone looking for a good time, a bad time, or money.  They were all untouchable in Kenny’s as long as the cops got their hundred and no one got shot.  

     Inside the front of Kenny’s was very dimly lit and there was no light at all as you moved further from the door.  In back there might be someone shooting up, or maybe a queen or two being intimate with a sailor-boy.  Everyone knew everyone. Straight men sometimes came there looking for a girl.  Any straight man or group was always welcome - sailors especially.  The Kenny’s crew would go out of their way to welcome newcomers.  On any given night there might be twenty or thirty regulars there - the finest the Tenderloin had to offer.  They were all waiting to make your trip to Kenny’s Upstairs a memorable experience.


     Just about 1:30 AM Phil the doorman at Kenny's let Tripper Bob in - they knew each other and got along well.  One of the bouncers was Tiger, an ex pro boxer who could be counted on.  Bob’s nose was running.  He’d lost the bounce in his step an hour ago; he was slowing down and not feeling well.  He crumpled into a chair at a small table facing the door.  

     Phil said quietly, “Shit Bob, you’re not looking good – dopesick?”

     “Yeah. You hear anything, let me know, okay?”

     “You got it Bob. Give me a while - could be a hot night.  I’ll find something.  If nothing turns up I’ll spot you a sawbuck to hold you over.”

     At two AM right on time, with the ironic, “Ain’t Nothing Like the Real Thing,” blaring on the Wurlitzer the show was on.  By 3 AM, Bob’s vision was becoming blurred, his whole body was aching, his nose was running like a river, and he was about ready to go out and stickup some schmo on the street.  A lot of people milling around, but Bob was becoming too sick, too fast, to pay much attention.  Sick as he was Bob noticed when Phil hurriedly walked over in his direction.  

     Grabbing a chair, sitting, and lighting a cigarette Phil said, “Group of three over there. The guy built like a grizzly bear has the money.  I saw hundreds, wallet’s thick with ‘em.  He’s a heavy boozer, big mouth, big guy, bad news if he gets hold of you.  That’s all there is right now.”

     Bob thought, “Looks like the schmo just came to me,” and asked Phil, “What about the other two?

     “I can separate them at the door when they leave. I’ll give them something to do – give you one or two minutes.  Oh, and Bob, don’t shoot him - awright?  I don’t know how the hell you’re gonna do it, this guy is three times your size and probably eats rocks for breakfast.  But just don’t shoot him – we don’t need the heat.  And get the hell out of there quick.  That’s all I can do man, good luck with this.”

     Bob warily asked Phil, “Gary around – does he know about this?”  If Gary knew there could be a problem.  The last thing Bob wanted was to have a problem with Gary.  He didn’t want to shoot him – but he would if he had to.

     “Naw, he’s on the lam.  Heat’s on for him big time.  Word has it he might have killed a squid outside the Trapp a few hours ago.  One hit, guy went down and didn't move.  So this is all yours, but you’re alone on it.”  

     The grizzly-bear guy and his buddies went to the back.  Two minutes later there was a scream, a thud, more yelling, another thud, and another.  The big guy came back into the light laughing and bragging.  A queen was out on the floor, along with two sailors.  No one knew what happened, no one asked.  Tiger and another bouncer ran to the back, but Phil quickly gave them the signal to back off, allowing the human grizzly and his buddies to stagger towards the front door as they loudly dared anyone to get in their way.  Phil had his work cut out for him.  

     While this was going on, Tripper Bob reached in his pocket, grabbed the half roll of bennies, popped them all, chewed them to a fine dust, grabbed someone’s drink at the bar, and washed down most of it.  The rest of the powdered bennies he snorted.  Then he waited.  He watched Phil and the three guys at the door.  It looked like Phil was working some kind of con or something, but whatever he was doing he had the attention of the grizzly bear and his two buddies.  This went on for a few minutes. 

     Bob could feel his eyes opening up and that nervous jolt as the bennies began to kick in.  He bolted upright quickly, brushed his hands back over his hair, adjusted his sunglasses, and straightened his three-quarter length black leather coat – Tripper Bob was ready to go.  

     The grizzly bear now fully enraged, bellowed to the others he was going outside to, “Find more queers to pound.”  Phil gave Tripper Bob the chance he said he would, he somehow got the bear’s two friends to go run back inside Kenny’s – right into Tiger.  Meanwhile shoving people aside, the grizzly stumbled and lumbered downstairs to the street.  A small crowd of people followed him outside because they knew he had too much money to be allowed to simply walk away - this was going to be tonight’s entertainment.  Some were going to watch, others might try, but whatever happened was going to be good.  Question was who was going to do what?

     One or two of the gunmen were quietly moving around.  It looked like they were going to get him as soon as he walked around the corner.  The drunken grizzly just stood there a minute waiting for his buddies when suddenly there was a blur.  A quiet flash of dark light, almost like a bolt of shiny black lightning and moving sideways - it just appeared without warning.  Even later no one was sure where it came from, maybe somewhere near the stairway to Kenny’s.  Everything suddenly seemed to be in slow-motion.  And there was no noise.  Almost like a Twilight Zone show.

     Tripper Bob wasn’t merely running, he was airborne, flying four feet off the ground - leather coat fanned over him like superman’s cape.  He landed behind the grizzly bear with both hands on top of the bear's pants.  With everything he had Bob tore downwards with so much force the enormous rip sounded like a train locking up its wheels.  And he got the grand prize.  

     For two seconds Bob stood there clutching the wallet triumphantly overhead with both hands displaying his trophy.  This was a beautifully done Tenderloin heist in full view for all to see.  Also in Bob’s hands was another trophy - a large piece of the guy’s pants and all of his underwear.  The trannies, queens, and just about everyone clapped and cheered.  Bob never heard it – he was gone.  Once he was around the corner Bob might as well have dropped off the face of the earth.  Half a minute later the grizzly’s two friends staggered downstairs, one spitting up blood, the other clutching his stomach in pain.  It seems they met Tiger . . .

     By the time they made it downstairs they found their leader standing on Turk street leaning against the lightpost outside the entrance to Kenny’s.  His pants were down to his ankles, no underwear, everything hanging out, frozen there, blank expression, with a crowd around him.  A few of the girls and queens were pointing and laughing.  Bob had ripped off the entire back of the pants.  His buddies tried flagging down a few taxis, but no cabbie was stopping for two guys bleeding and throwing up, with a half naked grizzly bear in shock and naked in the rear from the waist down.  It just didn’t look good - even for the Tenderloin.  Like I said earlier the Kenny’s Upstairs crew always tries to make a newcomer’s visit a memorable experience.

     And as for Tripper Bob, a minute later when the crowd broke up and things quieted down, KP picked up the sunglasses that Bob had dropped while he was flying – they were still intact - put them in his pocket, and casually went to his car.  He drove around the corner and up the block, stopping by a dark entrance to an apartment building.  Bob stepped out of the shadows and into Phil’s car. 

      Driving nice, Phil brought Bob to his place on upper Eddy Street.  There Bob quickly downed half a bottle of Nyquil Phil had on hand to hold him over.  He gave Phil some of the cash to hold for him, put the remainder in his pocket, and cleaned himself up.  Ten minutes later Phil drove Tripper Bob, wearing his sunglasses and carrying $1,200 in cash on him, to his dealer’s to score big . . .