Portland was the scene of Sammy Davis Jr.’s big break

Star performer of the Will Mastin Trio was a regular sight in Portland nightclubs during the late 1940s and early '50s; a telegram from old friend Frank Sinatra took him away to the big time.

EDITOR'S NOTE: A revised, updated and expanded version of this story was published in 2024 and is recommended in preference to this older one. To read it, click here.

By Finn J.D. John — November 27, 2011

If you hang around the right entertainment venues in Portland, sooner or later someone will tell you that Sammy Davis Jr. got his start here.

Well … that’s not exactly right. But the City of Roses definitely had a special place in Davis’s heart. You could say he caught his big break here — but it would be more accurate to say it was his big break that caught him, rather than the other way around. Portland just happened to be where he was when that finally happened.

Here’s the story:

On the Vaudeville stage at age 2

Sammy Davis Jr. was a showman born and bred. His parents were both respected Vaudevillians — his mother was a chorus singer and his father already a storied song-and-dance man, both of them living in New York when he was born. The gregarious young lad didn’t have a chance — he was sucked into show business at the age of two, when his dad took him on stage and sang with the lad in his lap.

They became a trio then — Sammy and his dad and his dad’s best friend, Will Mastin. They called themselves the Will Mastin Trio. Later, as little Sammy got bigger, they started calling themselves “The Will Mastin Trio Featuring Sammy Davis, Jr.” The kid was that good. But, of course, you knew that.

When World War II came along, young Sammy was called up as soon as he turned 18. The Army quickly figured out he was more useful on stage than he was in a trench, and he spent much of his time in the Army performing.

In the Army: Sammy’s loss of innocence

The Army was a horrible shock to young Sammy, who for the first 18 years of his life had never really left the world of Vaudeville performers. Like a lot of high-performance professions, Vaudeville was a world in which ability was king. A young black fellow on the Vaudeville circuit would certainly see some racism — segregated facilities, rude hotel clerks, that sort of thing. But it was nothing like the outside world. And it was nothing like the vitriol and outright hatred that young Sammy found in the Army.

This was somewhat ironic. It was the Army that taught a whole generation of white Americans to drop 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. For young Sammy, perhaps because the people he encountered weren’t in combat, the experience was much different.

It was particularly shocking for Sammy because 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.

But the Army was different. There was no mistaking getting one’s face spat on, wristwatch smashed and nose broken, or having racial slurs applied to one’s forehead in oil-based paint, as mere jealousy.

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

Sammy after the war

Sammy left the Army more determined than ever to use his talents to change the world in whatever way he could.

But 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 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.

Friends in high places

But some of Sammy’s old friends had made it big — really big. One of those people was Frank Sinatra. The Will Mastin Trio had performed with him in 1941. Now, in the postwar years, Sammy managed to reconnect with the Chairman of the Board, whose 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.

Sammy Davis Jr.’s Portland years

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.

But then, in 1947, a telegram arrived from Frank Sinatra’s agent, Harry Rogers.

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

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

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: Davis, Sammy Jr. & al. Yes I Can: The Story of Sammy Davis Jr. New York: Farrar, 1965; Stanford, Phil. Portland Confidential: Sex, Crime and Corruption in the Rose City. Portland: West Winds, 2004; Dietsche, Robert. Jump Town: The Golden Years of Portland Jazz. Corvallis: OSU Press, 2005)

TAGS: #PEOPLE: #famous #showmen #largerThanLife #charismatic #promoters #artists :: # #cultureClash #race-#black #showBiz #luckyBreak #underdog :: LOC: #pdx :: #157

 

 

 

 

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