As far as I know, aside from stamping out ice cream cones in a factory when he was a teenager, my father’s entire working career revolved around the selling of alcoholic beverages. He began as a high school student helping out in the tavern purchased by his father, who had accumulated a fortune building houses before losing it in the Crash of 1929 and trying another avenue to get back on his feet.

My father served as a gunner in the Air Force during WWII after graduating high school then returned home to complete two years of college pre-med courses. The subsequent choice to get married, however, tempered his ambition to become a doctor. He switched to business school and worked evenings in the tavern.

A year later he took his first full-time day job, peddling Narragansett beer—at that point the best-selling beer in New England and the chief advertising sponsor of the Boston Red Sox—to taverns and package stores around the city of Boston. His next and last job had him driving a similar beat, taking orders for wines and spirits distributed by the Italian import company Pastene.

The sales jobs provided his main income. It was partly out of obligation to his father that he continued to tend bar and help manage the tavern, which was called Tremont Gardens, on Tremont Street in Boston’s South End. Gradually my father assumed full management and ownership of the business. Later he purchased a second tavern, Tom’s Café, located in Mattapan Square, another area of the city. He would maintain these establishments into his fifties.

In the 1940s through the ‘70s, the South End did not sport the trendy reputation it has today. It was rugged, as was Mattapan Square. Operating a bar in such places during that era required one to position himself well with the right forces at the right times in the right ways. You needed… protection. Consequently, my father came to know and interact regularly with tough characters on both sides of the law: police, and mobsters.

An observant and crafty guy, yet a man of integrity and conservative by nature, he commanded respect amongst these types—or at least that’s how he told it. His success in running watering holes frequented by rough-around-the-edges clientele was largely due to the patrons’ perception of him as being “connected,” if you know what I mean. There, you were “connected” if you were part of the Mob. Which he certainly wasn’t. As he explained to me later on, he let people believe what they wanted.

He talked of breaking up fights in the bar. A graphic example was his rushing over in time to grab an angry arm poised to plunge a knife into some anatomy across the table. I guess emptying the till at night, or in the hours before dawn on weekends, and conveying the bag of cash down the street to the safety deposit box necessitated for many years his carrying a gun. He’d generally kept all specifics of his work with the taverns quiet from his family. (We never knew he had a gun.) Only once, late on a Saturday morning, when I was maybe 8 years old, did he take me inside Tremont Gardens.

The South End neighborhood started changing in the mid-70’s, for the worse as my father saw it, so he sold Tremont Gardens. Several years later he sold Tom’s Cafe, indirectly to one of Boston’s most notorious gangsters. (Perhaps I’d best not mention the name…) All the while, he worked full-time for Narragansett and then Pastene. When he was in his early sixties, another company took over Pastene’s alcoholic beverage division and terminated his employment.

He tried for a while to find other work but then settled into retirement. No longer was he a new-car-every-three-years man. Daily concerns with bars and liquor stores quickly faded into the past. Poker and Pinochle with his buddies, dutiful visits to his remaining siblings, brisk walks with a friend or two around the local mall, and late-night TV dramas became his routines.

Blocked arteries and heart attacks, then emphysema and debilitating chronic obstructive pulmonary disease, factored largely into his latter years. In 2006, at age 80, after an extended tour back and forth between the hospital and three different rehab facilities, he returned home with visiting nurses and hospice to live out his final four-and-a-half months.

My circumstances allowed me to spend at least a little time everyday with my dad throughout the challenging days of his decline. It was during a conversation one afternoon, about a month before he died, that a window opened up to give me a huge insight into a formidable dynamic between us. It shook my equilibrium.

Sitting back in his living room recliner, hands steepled on his chest, my dad had begun telling me about various package stores on his Pastene route. Little about package stores interested me, but it was comfortable terrain for him. Conversation never flowed easily between us, so in our constant unspoken mutual effort as adults to inch our way closer to one another, I stayed engaged and asked questions whenever he discoursed on his earlier life, wherever he went with it.

He’d been friends going back a long time with the owner of one of the package stores. The man was very successful, due to good business sense and an affable way with customers. Then he let his son take over the business. The son managed the store poorly and drove it into the ground. As my father spoke, a charged nugget of anger seemed to rush its way up his throat. An uncharacteristic look of disdain filled his face and surprising words of rebuke toward the younger man spilled out. I had never seen such an unpredicated expression erupt from this man I’d known all my life. It was a brief transformation but enough to push a sudden wave of painful realization over me:

I, his only son and only child, largely the object of his wife’s attention and affection, had been a good student, gone to a prestigious college (at his expense), become a childcare worker, moved to New York, then to North Carolina, and settled in as a preschool teacher. My career changed direction over the years, yet it never followed anything like my father’s.

It struck me hard in that moment as he denigrated the package store owner’s son that my father—regardless of how he felt now in his older, wiser, and perhaps more appreciative years—for much of his life never could feel proud of his own son. I had never come close to fitting into the tough-guy world to which he had grown accustomed outside of his family and home friends. The things I did, achieved, and accomplished never had value to him as they did to me. And for the longest time, I had neither money, wife, children, nor house—the kinds of ‘normal’ things he might appreciate. As both salesman and bar owner, he conversed continually with his predominantly male customers and assuredly listened to numerous reports about their sons’ male-world achievements. He probably fielded as many gripes about their sons’ foibles, but even those likely had a concreteness to which he could relate. All the while, he never felt comfortable talking to his associates about his one offspring, the childcare worker, the preschool teacher, the enigma. It would be embarrassing. I suddenly knew that, for decades, this had been a quiet, persistent source of pain to him.

I thought, what could I possibly do about this now? What could I possibly say to him? I could do or say nothing—not to him or to anyone else. All I could do was sit with this heavy awareness. I didn’t feel bad—only numbed by it. I gave no thought or analysis to this thing too overwhelming for words. I couldn’t begin to absorb the hurt that it held. Big blunt numbness just occupied me. There was no place else for it to go. I could do nothing about it. I carried it home with me. I brought it back with me. It stayed with me for three days.

Then amazingly, it lifted. The awareness of the past remained, but the weight and every painful molecule comprising it evaporated. Granted, I could not have changed how he saw the world in those days. I had nothing to apologize for, and who knows what might have been stirred up had I tried to address what I now knew to have been his experience? In such a touchy situation, I had a very slim chance of coming up with helpful words for either of us. Nothing about this prompted me to speak.

The fact is, the potentially crushing pain of knowing how my father had justifiably or unjustifiably felt about me for so long never materialized. It was as if a huge mass had fallen upon me; I’d felt it land, but only with a tiny fraction of its full weight; and then it was gone, in its entirety, for good.

• • •

I can only wonder how I could have ever achieved, in the past or the future, the sense of peace and closure I have now over this issue of my father’s long disappointment, had he not unwittingly opened the door that afternoon by evoking the package store owner’s son. Perhaps I would never have become aware of the secret dismay he’d felt for most of his adult life. Looking back, there were signs, and maybe subconsciously I was aware. But I never heard him speak disparagingly about my lifestyle or career choices to others, nor did I ever catch any glance or grimace that would have given a hint. Perhaps I would have lived out my life oblivious and unaffected. But I no doubt would have missed what I have now.

It is a mystery to me how or why, in the midst of that afternoon conversation, my father was prompted to show such rare expression, such that the message of his long-hidden frustration could be communicated so indirectly yet so fully to me, and I would become able to bear the burden of that intense awareness until it lifted and freed me.

I cannot say what, if anything, of an equivalent nature might have shifted in my father’s consciousness. Maybe dealing with the sudden, weighty awareness was a last piece that I alone needed to work out. Or maybe my tacit acknowledgment of his long-experienced pain freed something within both of us. Once I’d felt the relief, I wondered whether the same freedom had touched my dad. Over the three years that have passed since, I’ve grown more and more convinced that it had. As today, I feel… and appreciate… and reciprocate… his love like never before.