Letter From Milo: The Toughest Jew in Town

Gary, Indiana, in the middle to late 1960s, had a sizeable Jewish population. Like a lot of other families in town, including mine, many of the Jewish families were post-WW2 immigrants.

As is the case with most immigrant groups, Gary’s Jewish community was hard-working and industrious, their lives centered around traditional values like family, faith, education and a belief in a better future. Some did pretty well for themselves.

For example, there was a kid who went to my high school named Joey Stiglitz who was pretty good with numbers. Like any Gary kid with a knack for math, I’m sure Joey aspired to be a bookie. When that career choice fizzled, young Joey Stiglitz tried his luck in the field of Economics and eventually won a Nobel Prize.

I don’t want to give readers the wrong impression about Gary’s Jews. Not all of them were pillars of the community. They had their quota of drunkards, druggies, whoremongers, thieves, gangsters, bookies, murderers, tough guys and rotten bastards. Some of them, I’m proud to say, were very good friends of mine.

The Greene brothers, Stu and Ducky, were young thugs with bright futures as unlicensed pharmaceutical distributors. Another friend, Sonny Feigenbaum, spent more time in reform school than in high school. Morry Frank may have been, pound-for-pound, one of the toughest street fighters Gary ever produced. And, for all I know, my old poolroom companion, Josh Litvak, may still be serving out his life sentence for shooting two guys who he mistakenly thought were screwing his wife. Josh was always the jealous type.

Meyer Lansky would have been the second toughest Jew in Gary….

That said, the most feared Jew in Gary was a man who made other dangerous men tremble in fear. His reputation as a hard, unforgiving, vengeful badass was legendary. He was a mean, vindictive, cold-blooded, pitiless son-of-a-bitch with a long history of dealing with crime, violence and bloodshed.

His name was Judge Richard Kaplan and he ruled the Gary City Courthouse with an iron hand.

Although Judge Kaplan’s given name was Richard, he was known throughout the City as Judge Max Kaplan because he always handed down maximum sentences. Miscreants who appeared before Judge Kaplan always expected the worst and they were rarely disappointed. He believed everyone was guilty until proven innocent — and he refused to believe that anyone was completely innocent. Rumor had it that he once sentenced his own nephew to 30 days in jail for some minor infraction, although I doubt the story was true.

As far as I know, only one person ever got the better of Judge Kaplan – and that person was me. Here’s how it happened.

I was 18 years old and going nowhere. I had dropped out of college after one semester and was hanging around Gary, trying to figure out what to do with my life. One night I ran into some friends, went out drinking, got into a wild brawl, got maced by the police and ended up in jail. The charges were illegal possession of alcohol, public intoxication, creating a public disturbance, assault and battery and resisting arrest, although, to this day, I believe the last charge was a bum rap.

When I was released on bail the next morning, I was given some paperwork informing me of my upcoming court date, which was just a few weeks away. The presiding judge was going to be “the Honorable Richard Kaplan.” My goose was cooked. I was a goner, as doomed as it was possible for a young man to be. To make matters worse, I had a couple previous run-ins with the law, and I was fairly certain that Judge Kaplan would hold that against me.

That evening, I was hanging out in Stu and Ducky Greene’s basement with a few other guys, drinking beer and listening to the brothers’ collection of mostly shoplifted 45s.

“You are fucked, man,” Ducky said, sadly. “You’re looking at 90, maybe 120 days in Crown Point.”

”That’s if Judge Max lets you off easy,” Stu Greene added. “If he’s in a bad mood it could be worse. It’s a good thing you’re not Jewish.”

“Why’s that?” I asked.

“Because he’s extra tough on his own kind. He sent Sonny Feigenbaum to Plainfield for a year just for stealing a few cars. Said he was a disgrace to his family and his people.”

Dickie Kaiser, another friend who had an unpleasant experience with the City’s justice system, spoke up. “Too bad you’re not in the military. That’s Judge Max’s only soft spot. He takes it easy on soldiers. He’s an ex-Marine Captain, fought in World War Two.”

The next morning I went down to 7th and Broadway, walked into the Navy Recruiter’s office, and said, “I want to join up.” I spent several hours filling out paperwork. The only thing I had to do to officially be in the Navy was sign on the dotted line. But, I hesitated to sign. “Do you mind if I take these papers home and show them to my mom and dad?” I asked.

“You’re 18 years old. You don’t need your parents’ permission.”

“I know. But I’d like to show them anyway. I’ll be back tomorrow. I promise.”

The next morning I went down to the Courthouse, explained my situation to a secretary and asked to see Judge Kaplan in his chambers. After a two hour wait I was ushered into Judge Kaplan’s office.

“Tell me what you want and make it quick,” the Judge said, not even bothering to look at me.

The last place on earth I wanted to be was in a courthouse, talking to Judge Kaplan. I was nervous as hell, scared actually, but somehow I got through my poorly rehearsed pack of lies. I told the Judge that I was terribly sorry for any trouble I had caused. I explained that my inexcusable behavior was due to immaturity and the influence of bad companions. I said that I had given my situation a lot of thought and realized that by joining the Navy I would get away from bad influences and be in a disciplined situation where I would have the opportunity to become a responsible member of society.

Judge Kaplan quickly glanced at the Navy paperwork I laid on his desk, then looked at me for the first time. “I dislike young punks and criminals because they usually grow up to be old punks and criminals,” he said. “Had your case gone to court, it wouldn’t have turned out well for you. But I have a feeling that you’re a sincere young man. Your decision to join the military is a wise one, especially with our nation at war. I’m going to dismiss this case. Good luck in the Navy, son. Just remember, be on your best behavior. If you get in trouble, I can assure you that the officers who sit on military tribunals are not as good natured as I am. Now, get the hell out of my chambers.”

As soon as I left the Courthouse, I went back to the Navy Recruiter and handed him the paperwork. “I’m sorry,” I said, “But I changed my mind. I think I’m going to study for the priesthood instead.”

There was a strut in my walk when I left the Recruiters’ office. I was pretty proud of myself. I had gone into the lion’s den and come out without a scratch. I had outwitted the dreaded Judge Kaplan. I had gotten the best of the toughest Jew in town.

My euphoria was short-lived, however. A month later I received my draft notice. And a few months after that I was in Vietnam.

Many years later, when Judge Kaplan died, an old Gary friend sent me a copy of the judge’s obituary. When I read it I noticed that Judge Max had served on the Lake County, Indiana Draft Board, which meant that he had a say-so about which local boys were eligible for the draft. I imagine when he saw my name on the eligibilty list he didn’t hesitate to put a check mark beside it.

I opened a bottle of wine and spent some time thinking about my old Gary friends. Where were they, what were they doing? When my thoughts turned again to Judge Kaplan, a big smile spread over my face. Maybe, just maybe, the tough old bastard got the best of me after all.

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