My Brush with the Mob

Gary Indiana was built in the early 1900s. It started as a steel mill on the shores of Lake Michigan and the city was designed around the mill to house the factory workers. Gary was only 25 miles east of Chicago and a railway line connected the two cities. Soon there were many mills and a huge metropolis.

My mom grew up in Valparaiso, Indiana, which is very close to Gary. Her uncle Freddy was in charge of the numbers racket in Gary, and reportedly worked for the Chicago outfit run by Al Capone. But Uncle Freddy retired when the first big syndicate crackdown took place. His father (one of my great-grandfathers) had been a prominent rabbi in Chicago, and according to family legend, his dad never knew his son had become a gangster. My dad’s side of the family were mostly Germans who’d homesteaded in western Kansas after the Civil War and then drifted back to southeastern Kansas, a tiny town called Hepler. My parents met while attending Valparaiso University, a Lutheran college.

When my parents first began dating, Uncle Freddy would sometimes order his muscle to drive my mom and dad around. My parents told me about the parties at Uncle Freddy’s that they had attended. Freddy’s men also served as the bartenders and when they took off their jackets, they revealed their revolvers. No one messed with Uncle Freddy and his men.

Despite having a well-known local ex-gangster in the family, I never met any others and I don’t think the Jews in the USA ever created the sort of multi-generational crime families that were embedded in Sicilian society. We had some relatives that opened the Pink Pussycat strip club in Los Angeles, which became a favorite hangout for Frank Sinatra’s rat pack, though. The club even ran a school for strippers. My cousins went to California in the early 1960s, and even though they were underage, they were allowed to watch the floor show from backstage. Shortly after that, my cousin Tom bought a subscription to Playboy.

So that constituted my total awareness of the mob when I moved to New York around 1979. My first job in NYC was working as a reporter for Leo Shull’s Showbusiness, which really gave me a solid introduction to the seedy underbelly of Broadway (that’s Leo on the far left in the black shirt). From there I worked at several magazines, then the New York Daily News, and finally became a freelancer for a few years before I got hired by High Times. At first, that magazine was on the West Side near my apartment, but right after I got hired, they moved to 211 East 43rd St., which really disappointed me because that address was in the heart of midtown. I was riding a motorcycle at the time and midtown had zero parking for motorcycles.

However, on my first day to work, I decided to look around to see if I could find a free parking spot close to the office. I soon discovered a little horseshoe called Tudor City, a residential area hidden in the heart of midtown that allowed free parking on the street. I pulled into a spot next to a driveway and walked a block to work.

When Gary Pini heard about the location of my new office, he remarked there was a mob restaurant across the street. I never walked in the place. However, that night, when I went to pick up my motorcycle and drive home, someone had bumped my bike over. Fortunately, the damage was minimal. While I was picking the bike up, however, a black doorman appeared from inside the building and came out to talk to me. The upshot of his conversation was that there were some guys that parked here that I should not “mess around” with. I was too dumb, however, to pick up on his clues.

The next morning, I drove my bike back to the same location and pulled in between two cars, not wanting to park next to the driveway again. When I got off my bike, three dudes exited their vehicles at the same time and approached me.

“You can’t park here,” one of them said. These three guys did not look particularly intimidating. They certainly weren’t dressed in suits or expensive clothes.

“Why not?” I said.

“There’s not enough room,” he answered.

I looked around. There was plenty of room for my bike and I wasn’t really blocking anyone so I just said, “Hey, there’s plenty of room,” and just walked away off to work.

Many hours later, when I came back to ride home, I discovered the seat on my motorcycle had been completely slit from front to back. The knife had cut as deep as possible, so the seat was basically destroyed in a very violent fashion. I was thinking how dumb it was for those guys to do that since I knew who they were and what their vehicles looked like. My immediate thought was to whip up some concrete mix and stuff it into their three tailpipes.

When I got home, I went up to my apartment and got a needle and thread and some glue. I sewed the seat up (it took a hundred stitches at least) and then glued the thread so it wouldn’t come undone and the seal would remain water-tight. That night I realized my real situation. See, those three guys, they were obviously wise guys. I’d been warned by the doorman, and warned by them, and unless I got my act together, I was probably going to get kneecapped or worse.

So the next morning I parked on the other side of Tudor City and nowhere near where those guys kept their cars. I never saw or heard from them again, but it taught me an important lesson. When dealing with wise guys, make sure you read all the signals.