HANDSOME HOWIE

Handsome Howie was two years older than me, but at sixteen Howie looked like he was in his mid-twenties. While I was struggling with the embarrassment of acne, Howie was daily shaving his heavy black beard. He seemed to have skipped adolescence and preceded directly to adulthood. And it wasn't just physical maturity; Howie acted like a grown man conversing confidently with men and women much older. I and my callow friends were impressed and jealous - especially when it came to women. At sixteen Howie was dating college girls and rumor had it that he was sleeping with a sexy sales girl who worked at Marshall Fields Department Store. Imagine how impressive that was to me and my sex-starved fourteen-year-old pals. No question about it; Howie Shapiro was a neighborhood hero. The accolade wasn't as great as it would have been for a star athlete, but still impressive.

I didn't actually see that much of Howie. My connection to him was mostly through his brother, Ralph, who was my age and a friend. I think that Ralph was proud of his older brother while kind of resentful of his popularity.

Ralph, told me one day after school, "Mel, I hear all the time how cool, how good- looking Howie is. It's enough already."

"Yeah, that's gotta be annoying."

"Sometimes it gets to me; although I'll say this for Howie. He doesn't make a big deal about his looks or, what would you call it, charm. He doesn't brag."

"That's something."

"You'd think that with Howie's looks, he'd give up something in other ways -- like smarts. But he's a real good student, too. So am I, but it's like nobody notices."

"Well, like you said, he's not a dick about it."

Ralph and I remained good friends through high school at Lakeview on Chicago's north side and then both of us moved on to the University of Michigan in Ann Arbor. Two years earlier handsome Howie had matriculated at the University of Chicago on the city's south side. Ralph would fill me in on Howie's life, which was impressive. Howard Shapiro graduated magna cum laude from the University of Chicago. He was also elected student body president.

"What would you expect," Ralph said with a knowing smile.

The year was 1965. Much was happening in the world, but three things stand out in my mind: The war in Vietnam began in earnest; the use of marijuana, and to a lesser degree, LSD was becoming widespread; Sandy Koufax pitched a perfect game. Naturally, it was against my Chicago Cubs.

After graduating from the University of Michigan, Ralph and I continued our education. Ralph at Illinois College of Medicine and me at DePaul School of Law. Howie was already in his final year at the University of Chicago law school.

Ralph and I lived with our parents. Ralph, in the handsome 11th floor apartment of the Barry at 3100 Sheridan Road and I on the second floor of a three- flat building nearby on Aldine just a half block west of Lake Shore Drive. Howie had his own apartment in a high-rise building in Streeterville on the near North side.

"It's a really nice apartment in a great neighborhood. It must be expensive," Ralph grumbled one freezing morning in February when we had one of our infrequent breakfast meetings at the Pancake House just off Rush Street.

"Howie says he does some legal work for a couple of law firms. I guess they pay him well. "

"You know your clever brother; You can't be surprised."

"You're right, Mel. To tell you the truth, I wouldn't be shocked if I found out that Howie was making a bundle."

But Howie did surprise both of us after graduating from the law school, second in his class. Ralph half joked that he couldn't believe that anyone could beat his brother -- at anything. After passing the Illinois Bar Exam, Howie announced that he was moving to Miami, Florida to join a small law firm there.

Ralph said that he didn't get it.

"Howie was offered positions with all the top law firms in Chicago. Big money. Big future. And Miami - What does he know about Miami? "

Evidently, Howie knew quite a bit. He explained his decision to move to Miami to Ralph and me at his apartment while we helped him to pack the night before he was to make the drive to Florida.

"First, I'm ready for a completely new gig. I've been here all my life. No complaints, but this is the time in my life to start fresh where everyone doesn't know me since I was a kid. Different people - an entirely new environment. A fresh start.”

"Second, I don't want to be another cog in the machine of one of these huge law firms - working 80 hours a week. Maybe make partner someday if I don't make any waves. I don't see me doing that. This outfit I'm joining, Hardacre and Platt - they started just seven years ago. Smart guys. Young. Independent. From scratch, now they're one of the go-to law practices in Miami. Twenty very sharp lawyers. No fat. No corporate bullshit to get in the way. High on results, not corporate rules. I think that I've got a chance to write my own ticket.”

"And finally, it gets too damn cold here in the winter. I'm ready for sunshine and bikinis year 'round."

So in 1968 Howie became a resident of the Sunshine State. My conception of Florida at that time was that a lot of old people lived there as well as a big Cuban community. And also that the state produced an abundance of oranges. In the coming years, I was to learn much more.

I received my first piece of Florida news in a phone call from Ralph about a year later. "Here's one for you, Mel. My brother changed his name. He's now Howard, not Howie, Shepard. No more Shapiro. It's Howard Shepard."

"Why?"

He says Shepard is more business-like, less ethnic. By which I think he means less Jewish; although, he denies that."

"I don't get it."

"Either do I or my parents, but it's a done deal. He gets pissed off if I call him Howie. Frankly, I have trouble calling my own brother Shepard instead of Shapiro."

This name change was to be only the first of many changes that would foreshadow the life and times of Mr. Howard Shepard, of Miami formerly known as Howie Shapiro, once a resident of the city of Chicago.

Ralph and I were soon starting our third year in med and law school respectively when I received a call from Ralph. "He invited me to visit him in Miami for a week and he told me that you're invited too. What do you think?"

"I've never been to Miami. And the timing is good. I'm not scheduled to start the new semester for three weeks. How about you?"

"Same here and I could use a little vacation. I've been working my ass off in med school."

"I know the feeling. Where would we stay?"

 "Howie, sorry, make that Howard, offered his place. He says there's plenty of room for us. And here's the kicker, he's sending us two round-trip airline tickets."

"That makes it easy. A week in Miami absolutely free. Why not!"

"Yeah, why not?" Ralph replied.

When Ralph and I arrived at the Miami airport, a limousine was waiting for us. The driver, a friendly young man about our age, wearing a stylish, form-fitting black suit introduced himself as Robert. "Welcome to Miami. Mr. Shepherd sends his apologies for not being here. He's running late and will see you at the house for dinner at seven."

What I remember most about the ride to Howard's home was the weather. It was early January, snow, ice and shivering time in Chicago. Here in Miami, it was a radiant 78 degrees. A gentle breeze barely rustled the palm trees. Attire we viewed from our comfortable limo ran to comfortable short sleeve shirts and shorts in contrast to the bulky parkas favored in our Windy City this time of year.

In about a half hour, Robert pulled up to an imposing home adjacent to some kind of waterway or bay. The house was of a contemporary design - lots of glass, blended with steel and wood beams. To Ralph and me it looked like something right out of Architectural Digest. The lawn, which ran down to the water would not have been out of place on the eighteenth green at Augusta Golf Club. And flowers everywhere. Exotic varieties that I had never seen.

Ralph and I shared a bewildered look as if to ask, "Howie lives here?"

Our spacious room was tastefully finished in restful tones of beige and cream. Atop a large greenish, glass table, that seemed more sculpture than table, a ceramic vase had been placed containing more of those gorgeous flowers we had admired outside . I could not identify their pungent scent. Alone now, I spoke first. "Your brother lives here… by himself?"

"I don't know. It's a mansion."

"And what's with the chauffeur? You think Howie is putting us on?"

"I don't know. And remember, it's Howard."

"Whoever he is now, he's not living like the Howie Shapiro I knew in Chicago."

"Well, I guess we'll get some answers at dinner. "

We did and I must say that Howard was quite forthright in answering our questions.

"My firm bought the place in a foreclosure and offered me a great deal. My rent is a terrific bargain cuz part of my deal is that I kind of look after the property. Better all-around that the place isn't vacant."

"Are you the only one here?" Ralph asked

"There are a couple of housekeepers who come and go and a guy that lives on the boat."

"Boat?" I blurted out.

"Yeah it's docked right here. It's just a cabin cruiser - nice, but not a fancy yacht. Charlie is in charge of it. The boat and Charlie came with the bankruptcy."

Dinner was ordered-out pizza. Evidently a live-in chef was not part of Howard's deal. Afterwards, over a couple of beers, Howard brought us up to date on his life in Miami.

"It's been only a couple of years here, but I'm building a reputation. It's a different setup than in Chicago where connections are everything. I'm not saying that money or family isn't valuable here. It helps. But mostly what matters in Miami is smarts, talent, drive - whatever you want to call it. If you have it, you're not going to be held back by anything. "

"How's your - what can I call it - your social life? Maybe, I should say love life." I asked.

"You guys probably won't believe me, but the truth is that I haven't had time for a love life. I'm working all the time. Really."

"No broads in my brother's life. Now that's a change. Ralph said shaking his head in disbelief. “So tell us about what kind of law you're practicing."

"Hardacre and Platt is all about action - very fast paced. I learned right away that if you couldn't keep up, you were gone. Some smart, young lawyers couldn't handle it and quit or were let go. But I'll tell you this. If you had the smarts and the hustle – and okay - the balls, you could make big bucks. Not just that. I get a high going to work - like drugs without drugs."

"You make it sound like some kind of cult." I said.

"No - not like that. No blood oaths demanded. You just have to be sharp and not afraid to do whatever is needed to get the job done."

"You mean to win." I said.

"Yeah, you could put it that way." Howard replied.

As it turned out, Ralph and I saw Howard only two other times on our visit before returning to Chicago. Once, when he took us to a Jai Alai match and again when he joined us for dinner at a small, rather elegant restaurant where we were introduced to an unforgettable stone crab and shrimp dish. We, however, didn't engage much with Howard at that delicious meal because he was on the phone during most of the dinner.

In the next five years, I did not see Howard, although Ralph provided me with regular reports of his life in Miami. The information that I received related a story of great financial success. Ralph told me that his brother was now a senior partner at the thriving firm of Hardacre and Platt and a very wealthy young man.

In that half decade I had graduated from law school, passed the Illinois Bar Exam and was one of the many lawyers working in the State's Attorney's Office in Chicago assigned to the Criminal Prosecutions Bureau. Like Howard, I was young, however, unlike my fellow legal practitioner; I was very far from being wealthy.

Ralph had almost completed his residency in Nephrology at Northwestern Memorial Hospital in Chicago. He too was not rich. As a matter of fact, he was still living with his parents because money was tight. Ralph's financial problems were exacerbated by the fact that he and his girlfriend, Millie, wanted to marry - sooner than later. Howard had offered financial help, but Ralph was not the kind of person to accept it.

It was at that time that Ralph told me that Howard would be in Chicago in two weeks. The purpose of his visit was to introduce his fiancé to his family and friends.

The introduction to his betrothed, Katherine Elizabeth Reynolds , was held at the venerable Union League Club of Chicago. I was surprised that site had been chosen rather than the Shapiro's handsome apartment at the Barry. But Ralph informed me that Howard had invited over a hundred family friends and especially business associates to the party - far too many to be comfortably accommodated in the Shapiro's apartment . Clearly, three thousand square feet was not nearly enough space to properly entertain all these important guests.

My first impression on seeing Howard at the party was a bit of a shock. If Howie Shapiro at sixteen had looked like a man of twenty-five; the appearance of Howard Shepard now in his late twenties, was of a somewhat jaded gentleman of perhaps forty. Although still handsome, Howard's black hair had turned to gray at the temples and the beginning of a double chin could not be missed.

His soon to be wife, Katherine Elizabeth, (call me Kate) was tall and model – beautiful. A feeling of confidence seemed to flow from her. Even though she was a stranger to most of the crowd, she was in complete charge of the situation. Later, I learned that the Reynolds family was prominent in Florida Republican Party politics. It was rumored that Kate's father, Liam, owned several prime office buildings in Miami, Orlando and Tampa.

The invitation had described the party as informal, albeit the event was conducted in the Club's exceedingly formal, oak-paneled ballroom adorned with paintings of fine early American art. Cocktails and hor d'oeuvres. After about an hour of indulging themselves in those refreshments, the partygoers were formally introduced by Howard to his stunning fiancé. His speech was not long. I remember this line.

" I've been looking for Kate all my life. I'm a lucky guy. I won the jackpot."

 Personally, I wouldn't have portrayed his imminent wife quite that way, but I imagine that everyone there got the point.

I spoke to Howard briefly. As usual, he was in a hurry. So many influential guests with whom to chat. I understood. Howard asked perfunctory questions about my family, although he appeared to genuinely be interested in my job with the State's Attorney. I was fortunate to spend some time with Ralph whom I hadn't seen in months.

"So Howie is getting married. Did you ever think that would happen?" I asked Ralph.

"I honestly don't know, Mel. I haven't seen much of my busy brother these past couple of years. I guess we've both been busy."

"What do you think of the future Mrs. Shepard?"

"Well, she's keeping her maiden name, Reynolds – not Shepard. Howard is fine with that. Anyway I can't say I know her very well. She seems smart.”

"I know what you mean. I talked to her for a few minutes and she gave me the impression that she was really interested in what I said. "

"Yeah, no question – Kate will be good for Howard."

Another three years flew by. I didn't think much about Howard. Then one morning at my office, I got a phone call from my boss, Dan Sullivan.

"Mel Rosen, I understand that you know a guy, Howard Shepard."

"I do. I've known him since I was a kid. His brother is a good friend. Why do you ask?"

"I heard that you might know him and I wanted to talk to you about him. I don't want to get ahead of myself, but Mr. Shepard is part of a joint investigation involving our office and the Miami District Attorney office."

"Howard Shepard? Investigated for what?"

"Look, Mel…nothing is final right now. But Mr. Shepard may be involved in some serious shit."

"Like…?"

"Drug trafficking – big time."

"Christ Dan. Howard is a real estate lawyer. I can't imagine him as a drug dealer."

"I'm sorry to be the one to tell you, but your old pal, Howard, seems to have gotten himself involved with some very bad people. "

"He's a partner in a top Miami law firm. I don't get it."

"Hardacre and Platt, right?"

"Yes."

"They're a big part of the problem. Hardacre and Platt represent the Sinaloa Cartel. As far as we've discovered, almost all of their business involves the cartel."

"My god, Dan. I can't believe it."

"I'm afraid it gets worse. Mr. Shepard is in a very bad place. Our case against him and his partners is solid - more than solid."

"When you say drug trafficking, what exactly do you mean?"

"Essentially, being a principal participant in the smuggling of illegal drugs into the United States and distributing said drugs."

"Fuck me."

"More like fuck him. Mel, I'm not telling you this for kicks Howard Shepherd is in deep shit. His choices are all lousy, but the one we can offer is his best option. You know this guy. Maybe he's more likely to listen to you than to strangers."

"I don't know that he'll take any advice from me. I think that he considers me a kid from the old neighborhood who is a pal of his little brother. "

"Well, you're our best shot - his best shot."

"What can you offer him?"

"The moon and the stars. A get out of jail card."

"Please, in plain English, Dan."

"Bluntly put, here are his choices: One - fight us and go to trial . It's never a slam dunk, but he'll very likely be convicted and spend at least the next twenty years in a maximum-security prison. Assuming, the cartel doesn't kill him before he ever gets to court or once he gets to prison. Or two: cooperate with us . Provide us with names, dates, all the details of the operations - the whole nine yards. We have most of it already, but there are a few blanks that Mr. Shepard could fill in. We'll protect him 24/7 and then place him and his wife in a super-secret witness protection program where no one will ever find them. A new life - new identities. A chance - his best chance."

"You're my boss, Dan. Are you telling me to do this?"

"Mel, this isn't the army. It's not an order, but you're in a unique position to help us as well as a friend in a huge jam. And yes, it's a plus for your career here."

You lead a predictable life. You go to work. You like your job. You think that you're making a contribution to society. You're getting ahead. The future looks promising. Then you get an unexpected call from your boss and your life is turned upside down. That was my dark thought as I stared into the blacker sky from my window seat on my flight to Miami that night.

My instructions for meeting with Howard reminded me of the intricate plotting of John Le Carre novel. Our secret discussion took place in the dental office of Sidney Kanter, DDS. Doctor Kantor was not present. I never met him, but an unoccupied room among his offices served as the site for my conversation with Howard.

Dr. Kantor was Howard's dentist. Our clandestine meeting was being arranged there because it would arouse no suspicion among those who would be disturbed or worse by a meeting involving Howard and a government legal representative.

The room was sparsely furnished - two chairs, a desk , bare walls. While I waited, I thought about Howard Shepard (formally Howie Shapiro) and the curious nature of this interview. I had been instructed to present our proposal to Howard as not negotiable - take it or leave it. It was alright for me to listen to anything that he had to say, but to make sure that he knew that I was not there to bargain. I was there as an old friend who had been given the assignment of delivering the best, the only deal he would receive. Somehow fate had determined that I would be the bearer of this life-changing information. It was a job that I did not want.

As I was nervously musing, Howard walked briskly into the silent room. I had not seen him since the union club introduction of his then fiancé. Howard was attired in a perfectly tailored blue pin-stripped suit. the knot of his cyan silk tie complemented an egg -white dress shirt; although, the large diamond cufflinks struck me as a bit much. Howard did not look like a man in grave trouble.

He flashed a perfect bright smile (Dr. Kantor could be proud of his work) and addressed me in the confident matter of an extremely successful attorney.

"Long time no see Mel."

"I'm sorry it's under these circumstances."

Howard slipped into his chair across from me and exhaled a big, audible breath. Close up I saw that the old neighborhood handsome hero had aged badly. His hair was now all grey – with an emerging bald spot at the crown. His body did not appear fat, but his face was bloated and there were gray bags under his eyes.

"Me too. I didn't think that I'd ever be having this conversation with you, Mel – or with anyone. Have you talked to my brother?"

"No, I was instructed not to speak to anyone about this."

"Well, so you know – he knows. I told him. But my folks don't know. I'd like to keep it that way for now."

"I certainly don't plan to say anything to them."

"Thanks. So let's talk about what brings you to Miami."

"Howie, sorry Howard, I'm just the messenger. I think that the idea of my bosses is that hearing this deal would be better coming from someone you know than from strangers."

"Maybe, but frankly what's most important to me is the deal you're delivering."

"I understand. Here's the deal in a nutshell.” I then carefully spelled out the offer my superiors had given me to deliver.

Howard listened carefully while I laid out the details. He did not interrupt me and it was impossible for me to read his reaction as I studied his facial and body language. When I was finished, he asked me a question.

"That's it?"

"Yes. As I told you, there's no wiggle room."

"You did. So it's a take it or leave it deal?"

"They emphasized to me that this was the best and only deal they would offer."

"And you're only the delivery guy? No negotiating with you?"

"No, I'm instructed to make sure that you understand the terms of the deal being offered. I can note your response, but I cannot work out any other terms."

"Yes, as you said, you're just the delivery guy."

"That's exactly right."

"Well, Mr. Delivery Man, what do you think – any ideas – any advice you have for me?"

"Come on, Howard. I can't tell you what to do. This delivery job is one I wish I wasn't given. All that I can tell you is that I'm sure my bosses do not see this offer as a trial balloon. I know these guys. They are not fucking around. They need you a little - not a lot. I believe them that this is take it or leave it – period."

"And how long do I have to decide?"

"The offer is good for 48 hours."

"It's a hell of a thing, Mel, Howard sighed. "You know, I figured that I'd come a long way since those days when I used to hustle broads on Rush Street. Now, I've got 48 hours to try to salvage my life."

"Howie, I wish it wasn't so. I'm not here to judge you. You made some very bad decisions. I suppose we all do, but yours come with big time consequences. For what it's worth, I'd take the deal they're offering."

"Did your bosses tell you to say that?"

"No, that's my own advice."

"Thanks for your (Howard paused for perhaps five seconds as he searched for the correct word) honesty."

Then the once best looking , coolest guy in our old neighborhood rose from his chair, adjusted the cuffs of his crisp dress shirt to make sure that they showed just the right amount of white and diamond cufflinks, and with a too enthusiastic smile turned to me and said –

"See you around, pal."

I never did. Although, I did speak to him 24 hours after our meeting when Howard told me that he would take our deal. He said that he had a long and difficult discussion with his wife. The witness protection program was anathema to Kate; she would not be joining him in witness protection. That blow I thought must be devasting to him and I told him so. Howard, his voice barely audible, replied that he had hoped more than anything else that Kate would stay with him. He pleaded with her - acknowledged that the deal was extremely tough for both of them, but it gave them a chance for a new life. Kate was not moved. She told Howard in what he described as an icy voice that she did not want a new life. Her life and family she said, with the force of a blow, had been wonderful – until he ruined it. But she had no intention of running away in shame and disgrace. That was his problem. She would pick up the pieces and make a new life. She would not let Howard take her down with him. Howard made it clear to me that he would not judge her, but that his heart had been broken. I made a feeble attempt to lift his spirits by suggesting that in time he and Kate might reunite. Not likely, he mumbled and said that he did not want to talk anymore about Kate. He urged me to stay close to Ralph and to his parents. He could not talk about his soon to be new life but hoped for the best. He indicated that he was being closely guarded by the government prior to trial and that he was grateful for the protection but regretted the loss of freedom. His voice cracked when he told me that he accepted everything that he was about to lose. He could live with that, but the loss of Kate might destroy him.

Three months later, I was half watching the late news on Channel 2 in my Chicago apartment. The mention of Howard's name grabbed my immediate attention. An image of several FBI agents in a crowded Miami apartment. A body covered by a black canvas sheet. The agent in charge formally answering the reporters tense questions.

"Mr. Shepard was shot by a sniper when he stepped onto the apartment balcony. An agent accompanied him, but that agent had not been hurt. Mr. Shepard was hit by one bullet, which struck him in the left temple. He died instantly. A search was immediately conducted to find the shooter, but was unsuccessful. Our investigation continues."

I suppose that I'll never know the truth about Howard's violent demise. At least three government investigations produced an abundance of information, but no clear answers. That he was murdered was apparent. Who was behind the killing? Take your pick: The drug cartel, his law partners, a corrupt guard. One rumor even had his father-in-law involved. Another bizarre theory suggests that Howard arranged his own suicide. Ultimately, no one was ever brought to trial for Howard Shepard's tragic end.

Now, fifteen years after his death, the story of Howard Shepard is an ever-dimming memory. But for a handful of us who knew him 'way back' when he was Howie Shapiro, the handsomest, smartest, coolest guy in the neighborhood; we'll never forget.