Sammy Davis Jr. once called Portland home

By Finn J.D. John
April 21, 2024

EDITOR’S NOTE: This article is a rewritten and re-researched version of a much shorter article published Nov. 28, 2011, which you can find here.

BACK BEFORE WORLD War II, when racism was still a mainstream attitude with little or no social stigma attached, Portland was not a very friendly town for Black people.

It’s not that way any more, of course. There’s still racism; but the toxic race-hierarchalism that winked at lynchings and enabled the rise of the Ku Klux Klan — that, thankfully, is a distant and uncomfortable memory today.

And one has to wonder how much of that transformation — not just in Portland, but around the nation — can be attributed to the influence of one man, a man still today widely known as “The World’s Greatest Entertainer”: Sammy Davis, Jr.

Davis came to Portland with his dance group, the Will Mastin Trio — composed of Davis, his father, and his father’s best friend, Will Mastin — just after the Second World War. For a little while he was a regular in P-town’s clubs and Vaudeville theaters. In fact, he was in Portland, performing a regular run at Amato’s Supper Club with the Trio, when he got the telegram that changed his life forever:

“OPEN CAPITOL THEATER NEW YORK NEXT MONTH,” it read. “FRANK SINATRA SHOW. THREE WEEKS. $1250 PER. DETAILS FOLLOW.”

It was signed by Harry Rogers. Rogers was Frank Sinatra’s agent.

After getting that telegram, the three of them had to sit down for a bit.

“We passed that telegram back and forth like three drunks working out of the same bottle,” Sammy wrote in his memoirs, many years later.

They knew what it meant. It meant instead of going down slowly with the sinking ship that was the local Vaudeville theater industry, they were about to go nationwide.

SAMMY DAVIS, JR. was born into show business. He first came on the scene on Dec. 8, 1925, in Harlem; but he first made the scene just three years later, as a tiny toddler playing a bit part in a Vaudeville revue show called “Struttin’ Hannah from Savannah,” as part of the Vaudeville troupe his parents were part of.

Both of Sammy’s parents — Sammy and Elvera Sanchez Davis — were respected Vaudevillians. Elvera was a chorus singer, and Sammy Sr. was already a storied song-and-dance man. Both lived in New York and were part of a Vaudeville troupe led by performer-impresario Will Mastin.

At nearly the same time, Sammy Sr. and Elvera’s marriage broke down, and she quit the Mastin troupe and joined with a competitor. With fewer childcare options, Sammy Sr. started bringing the boy onto the stage more and more.

And little Sammy loved it. If you grab a dictionary and look up the word “Natural,” as in “the kid is a natural,” a picture of young Sammy Davis Jr. will be right there on the page. (Well, no, it won’t, but it should be.)

As little Sammy got older, he soon left bit parts behind, and Mastin and the two Sammys formed a song-and-dance group, calling themselves “The Will Mastin Trio.” Not long after that, they changed the name to “The Will Mastin Trio Featuring Sammy Davis, Jr.” The kid was that good. But, of course, you knew that.

For the elder Sammy Davis, what had started as an alternative to finding a babysitter soon evolved into battles with truant agents trying to force the boy to stop performing and attend grade school.

The legend is that the Trio’s response was to move on to the next town on the Vaudeville circuit they were working and introduce the 8-year-old Sammy Jr. as a 16-year-old “midget.” The story seems hard to buy with a straight face; but maybe the truant agent was willing to play along. Or maybe he was one of those “all Black people look the same to me” types and couldn’t tell the difference. Either way, Sammy was allowed to be essentially home schooled.

Possibly his most influential teacher was the tap-dancing legend known as Bojangles Robinson (the original Bojangles, not the street performer Jerry Jeff Walker met in the drunk tank in New Orleans and wrote a song about. Later in his career, Sammy would make Walker’s “Mr. Bojangles” his signature song, though.)

Sammy met the great Bojangles when he was 9, and Bojangles was about 44. He gave young Sammy the piece of advice that he would literally build his whole career on: Always make it look easy, and never let the audience even catch a glimpse of how physically demanding the act is. In fact, the more obviously strenuous the act, the more important this illusion of effortlessness becomes.

Of course, Sammy would likely not have had the chance to meet Bojangles and learn from him, if he’d been parked in a third-grade classroom somewhere like Tulsa or Atlanta.

But Sammy’s lack of public-school experience would have some rough consequences later in his life — not because of lack of knowledge, but because of lack of experience with racism in mainstream American society.

Because Will and Sammy Sr. largely protected little Sammy from any experience of 1930s-style racism. And the Vaudeville scene didn’t really show him any either. Like a lot of high-performance professions, Vaudeville was a world in which ability was king. And from infancy, Sammy Sr. and “Uncle Will” Mastin had shielded him from even what (relatively) little racism there was in Vaudeville. “That man was just jealous ‘cause we’re in show business and he’s gonna be pushin’ beans all his damned life,” Sammy Sr. told his young son on one occasion, after a drugstore lunch-counter clerk dropped an N-bomb on the three entertainers and ordered them to sit at the “colored” end of the counter.

A young Black fellow on the Vaudeville circuit would certainly see some racism — segregated facilities, rude hotel clerks, disrespectful white people at venues — and would quickly figure out that discrimination existed. But to learn about the dangers of knock-down-drag-out toxic-racist cruelty, one had to go outside that world a bit — to a segregated public school where other, less-sheltered kids could tell you about it, or … or into the United States Army, where you could experience it firsthand.

THE ARMY WAS a horrible shock to young Sammy Davis, who was drafted when he turned 18 in 1943. Throughout his life, Sammy had learned to deploy his talents — by now he was a gifted performer who could tap dance, sing, do celebrity impressions, and deploy his magnificently expressive face to great comedic effect — to charm people and make them like him.

This did not work in the Army. Fellow draftees and drill sergeants and officers in the Army came from all over the country, including parts of it where segregation and racial roles were so locked down that even meeting a white person’s eyes and smiling at him (or, worse, her) was evidence of a kind of insubordination punishable with attempted murder.

And attempted murder — the kind where the person administering a beating clearly doesn’t care if it’s fatal or not — became a part of Sammy’s life, for the first time, in the Army. His father’s pocket watch was smashed, and so — several times — was Sammy’s nose. It ended up permanently flattened.

Eventually the Army figured out that Sammy would be more valuable as an entertainer than as a combat soldier, and after that he got better protection. He still never got promoted, though, and mustered out of the Army at the end of the war holding the same rank he had coming in: Private.

It was all somewhat ironic. It was the Army that taught a whole generation of white American men to question their racist views, which they found hard to square with what they learned of the quality and character of Black soldiers who fought beside them and occasionally saved their lives.

But for young Sammy, perhaps because the people he encountered weren’t real combat veterans, the experience was much different.

It was a harsh way to lose one’s innocence, and it left an unmistakable bitterness that took a long time to fade.

But it left something else, too. There is an old saying that the fire that burns the straw also purifies the gold. Sammy left the Army more determined than ever to use his talents to change the world in whatever way he could.

But there was no denying that he was profoundly demoralized. You can’t mistake the bleakness in his prose when he writes in his memoirs about that time in his life. Where once he’d been a proud show-biz man, feeling like his life was glamorous and going places, now he felt the rut he was in.

And by now it was definitely a rut. The fortunes of the Will Mastin Trio were fading like the Vaudeville era they were part of — fading to a starvation diet of bad-paying shows in different towns, to occasional grueling strings of one-night stands, to the dreaded day when they’d have to give it up and start “pushing beans” themselves.

Some of Sammy’s old friends had made it big, though — really big. One of those people was Frank Sinatra. The Will Mastin Trio had performed with him in 1941, when Sammy was just 15 and Old Blue Eyes was 26, and the boy had struck up a strong friendship with the legendary Chairman of the Board. Back then, Sinatra had been just another promising young singer, but now, in the wake of the war, his star was rising like a rocket.

It was good to have successful friends, but that didn’t pay the bills. Sammy’s group played on. Los Angeles, Chicago, Boston … Portland.

The Will Mastin Trio was in Portland for two years, playing regularly in the Clover Room nightclub, among other local hot spots. Sammy and his team were one of Stumptown’s hottest draws, but still, it wasn’t exactly a prestige gig. Although it had a sizzling jazz scene at the time, Portland was not an A-list town, and it was on the way to almost nowhere. Portland has to have been one of the lowest points for the trio. It’s certainly among the least important cities they performed in.

But Sammy was a showman. He loved to be loved. And there’s no question but that Portland loved him. Plus, there may have been racism in Portland, but at least it wasn’t a back-of-the-bus-boy kind of town. He doesn’t talk about this in his memoirs, but it’s at least possible Sammy was planning on sticking around a while, settling for being a big fish in a small pond.

And, that’s where he was when that fateful telegram arrived from Frank Sinatra.

Significantly, Sammy stuck around Portland for several years after his big break, basking in the glow of its audiences and hanging out with its show-biz people, as his career started lifting off — stuck around well after his roster of options had expanded to include much more prestigious cities.

After 1947, the Will Mastin Trio was on its way … with a little help from an old friend. Life for the three of them would never be the same. And for fans of Frank Sinatra’s “Rat Pack,” it would be remembered as the dawn of a golden age.

(Sources: Yes I Can, a book by Sammy Davis Jr. published in 1965 by Farrar; Portland Confidential, a book by Phil Stanford published in 2004 by West Winds Press; Jump Town, a book by Robert Dietsche published in 2005 by OSU Press; “1925-1950: Early Life on the Road,” an un-by-lined biographical essay published on sammydavisjr.info, an independent fan site)