When I was about eight or nine, our family had a tradition of escaping the northern winters and heading down to North Miami Beach to visit my grandmother. It was a time before cell phones, internet, and helicopter parenting — when kids were free to explore, get into trouble, and stumble into stories that would sound unbelievable years later.

During one of those winters, I met a man named Ruby. He was older — at least to my young eyes — maybe in his 60s or 70s. He wasn’t family, but he felt like a sort of honorary uncle. Ruby had a boat and a calm, easy presence. He didn’t talk down to me like a lot of adults did. He listened, told stories, and laughed easily. For reasons I still don’t fully understand, he took a real liking to me.

Almost every day, Ruby would take me on his boat to the Diplomat Hotel, a grand resort on the water in Hollywood, Florida. It wasn’t just a hotel — it was one of the places. Even then, without understanding why, I could feel the energy. It had palm trees that seemed taller than the sky, bellhops in white gloves, a marble lobby that echoed every step, and the kind of buzz that made you feel like something special was always about to happen. And usually, it was.

We’d pull the boat up to the dock like it was the most natural thing in the world, walk through the back entrance, and head into the restaurant or bar area for lunch or dinner. Ruby was well-known by the staff, and nobody ever questioned why he brought a kid along. They always had a table for us.

Eventually, the staff got to know me too — but more surprising, so did the guests. And not just any guests.

What I didn’t know at the time was that the Diplomat was a magnet for the stars. It was where celebrities stayed, where musicians and comedians performed, and where the Rat Pack partied when they weren’t in Vegas. And somehow, I had wandered into that world, totally unaware that it wasn’t normal to be chatting over a sandwich with Sammy Davis Jr.

Yes — Sammy Davis Jr.. He was one of the first big names I got to know. He was funny, kind, and generous with his time. I must have amused him, because he always welcomed me over when he saw me. It started there. And then one by one, the circle grew. On any given day, I might have lunch or dinner with Frank Sinatra, Dean Martin, Bing Crosby, Maurice Chevalier, Art Carney, or even Jackie Gleason.

Looking back, it feels impossible — like a daydream stitched together from old records and black-and-white movies. But it was real. These men were legends to the world, but to me, they were just the guys at the next table who liked my boat stories and didn’t mind footing the bill for a burger.

By the time I turned ten, Ruby gave me a gift I’ll never forget — a 16-foot boat. It was old, a little beat-up, but fully mine. That boat became my passport. I would cruise up and down the intracoastal on my own, feeling like the king of the world. And yes — I kept going to the Diplomat, on my own now. I'd pull in, tie off, walk inside like I belonged (because at that point, I really did), and wave to whoever was around.

The stars saw me as a little novelty. I was that bold, funny kid who showed up alone by boat, sat at their table, and never acted starstruck — because I honestly didn’t know I should be. That innocence made it work. They’d laugh, buy me food, and tell me stories.

Some days it was just Sammy and me. Other days were something out of a Hollywood dream: Frank, Dino, Bing, Chevalier, Art, and Jackie — all at the same table, sharing laughs and drinks while I sat there with wide eyes and zero understanding of how rare that was.

One day, I finally told my father. I remember casually mentioning over dinner that I’d been eating with Sammy Davis Jr. and friends, and that they usually picked up the tab. My dad gave me a look. You know the one — the classic “you’ve got a wild imagination” look that parents perfect by the time their kids can talk.

He didn’t believe a word of it.

So I said, “Fine. Let’s go. I’ll introduce you.” He called my bluff — and off we went. Not by boat this time, but by car.

We walked in through the front entrance. I led him toward the restaurant, and like clockwork, there was Sammy Davis Jr., sitting near the back. I walked up, said hello, introduced my father — and Sammy stood, shook his hand, and invited us to dinner.

Then, something incredible happened. Over the next 30 minutes, Frank Sinatra, Dean Martin, Bing Crosby, Maurice Chevalier, Art Carney, and Jackie Gleason all arrived.

It was like a scene from another era. My father sat there in stunned silence, watching his son being treated like one of the gang by some of the most famous entertainers of all time. He didn’t say much that night. Honestly, he couldn’t. But I’ll never forget the look on his face. He looked at me differently — with a kind of awe I hadn’t seen before. That moment changed something between us. I wasn’t just a kid anymore. I was someone with stories, someone with a life outside of what he imagined for me.

Not all the stars were as friendly. Jackie Gleason, for example, wasn’t quite like the others. He had a reputation, and even as a child I could sense it. He could be gruff, impatient, even rude. He once brushed me off mid-sentence and gave Ruby a dismissive glance. I didn’t take it personally — I just noticed. Art Carney, on the other hand, was a complete gentleman. Warm, attentive, humble. Their personalities off-stage were a real contrast to their TV personas.

All of that — the boat, the hotel, the stars — became a core part of my childhood. But more than the glitz or the stories, what stayed with me was the unexpectedness of it all. I didn’t chase it. I didn’t plan it. I just showed up with a bit of curiosity and the willingness to say hello. That was enough.

Now, decades later, it feels like a dream I got to live while the world wasn’t looking. Those moments remind me that sometimes the most extraordinary things happen when we least expect them — and when we don’t even know they’re extraordinary.

And to think, it all started with an old man named Ruby... and a little boat.