Life on the Corner: Cadillac Sam

Back in the 1960s limousines were a rarity in Boston. They were luxurious, elegant, and expensive, you had to be either very rich or very dead to afford one. Undertakers used them for funerals and rented them out for weddings so riding in one was a special treat. In all of Boston there were only a few limousine services but, strange as it may sound, there was one such limousine company right here in the North End.

One of my father’s friends, and a regular in Nick’s tavern, was a guy called Cadillac Sam. When I knew him Sam was an old, thin, stooped, white haired man who always dressed in black. Black pants, black shoes and socks, a thin black tie with a pure white shirt and a black jacket. Sam was right out of central casting as the perfect funeral driver.

Sam somehow came up with an enormous, black Cadillac Fleetwood limousine and that car was Sam’s baby. He kept it immaculate, constantly giving it Simonize jobs and vacuuming the interior. That limo was so beautiful I thought Sam slept in it, but in reality he had a small apartment on Fleet Street where he lived with his wife, a brassy, bleached blond who was committed to spending all his money.

The North End at that time had several funeral homes so Sam was kept busy most weekday mornings going to and from the various Italian cemeteries, which left his afternoons free to hang out in my father’s bar room. There was a wall telephone near the back of the tavern where the resident bookie, Shamricki, took action. Sam gave out that number as his office phone which annoyed Shamricki, especially when there were lots of calls coming in to place bets. 

Sam sometimes got calls from booking agencies asking him to chauffeur celebrities around town. He loved doing those jobs because the tips were much better than what he got from grieving relatives at a funeral. One day I was hanging around in the tavern when Sam got a call to ask if he could pick up a VIP at Logan airport and bring that person to McLean’s hospital in Belmont. Sam quickly agreed and off he went. About an hour later his limousine pulled up in front of the tavern and parked with two wheels on the sidewalk. Sam got out and came into the store where my uncle, Willie, was tending bar.

“Willie,” he said, “Let me have a double shot of brandy for my client in the car.”

My uncle reached for the bottle of Metaxa on the first shelf.

“No, no,” Sam said, “Not that. Give me the good stuff on the top shelf.”

My uncle reached up for the squat bottle of Courvoisier, VSOP and poured two fingers into a cocktail glass. “Who’s the celebrity” he asked?

“I can’t say, Will,” Sam replied, ”She doesn’t want anyone to know she’s in town.” 

Well, now my curiosity was peaked and I knew the person in Sam’s car was a woman.

About ten minutes later Sam came back in and ordered a second double of brandy.

“What’s going on?” Willie asked. “That’s a lot of booze.”

“I’m driving her to McLean’s out in Belmont,” Sam replied, “Where she’s going to dry out for a month. This is the last chance for her to have a drink before she goes cold turkey.”

Well, now my curiosity was peaked. There was a woman celebrity in Sam’s car and I wanted to find out who she was. I tried acting nonchalant, followed Sam out to the car and leaned against the brick wall.

Sam tapped on the darkened rear window and the woman in the back seat rolled down the window part way. As she reached out her hand to get the brandy I could see the top part of her face. She saw me staring and gave me a wink and I almost fainted. Those dark twinkling eyes, the short black hair, it was Dorothy from the Wizard of Oz, Judy Garland. 

Sam didn’t wait for her to finish. He got in behind the wheel and drove off. When he returned later that day he confirmed that his passenger was indeed Judy Garland. She had entertained him all the way out to Belmont with stories and tipped him generously. He said Judy was his favorite client ever. All this took place around 1966. A few years later Judy Garland died of an accidental drug overdose at only forty-seven years of age. A great talent was lost.

Judy Garland is best remembered for her role as Dorothy in the Wizard of Oz where she sang Somewhere Over the Rainbow. I heard an interview with her where she said that wasn’t her favorite movie. She was only sixteen years old when she made it and, much to her annoyance, the Munchkins acted up on and off the set. A much better movie was Meet Me in St. Louis. Judy was a bit older when she made that film and her future husband Vincente Minnelli was the director. In it she played Esther Smith, the older sister of Tootie Smith played by Margaret O’Brien, another famous child actress. In the film Judy sings two of her most famous songs, the Trolley Song and Have Yourself a Merry Little Christmas. You’re a tougher person than I am if hearing Judy sing Have Yourself a Merry Little Christmas to her baby sister doesn’t bring tears to your eyes.

Nicholas Dello Russo is a lifelong North Ender and columnist. Often using vintage photographs, Nick tells the stories of growing up in the North End along with its culture and traditions. It was a time when the apartments were so small that residents were always on the streets enjoying “Life on the Corner.” Read more of Nick’s columns.