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New era for ‘Miss Careful’ at San Jose’s Diamond Laundry

The past few decades had not been kind to “Miss Careful,” the icon featured on Diamond Laundry and Cleaners’ wooden billboard sign. For years, her image greeted the dry cleaning store’s customers and drivers heading into downtown San Jose on San Carlos Street. Over time, though, the sign’s paint had faded and chipped away, and pigeons began using it as a roost, leaving deposits dripping everywhere.

But by the end of last year, things brightened dramatically. The old sign was torn down and replaced with a new one, its color scheme and design matching a version from Diamond Laundry’s heyday in the early 1960s. San Jose artist MESNGR recreated the hand-painted lettering and updated “Miss Careful,” with a look that somehow manages to be both retro and modern compared to previous incarnations.

This month, Jason C.H. Burton — who now runs the business his grandfather, Harold H. Hulbert, started in 1931 — brought his grandmother, Mary Jane Burton, to see the new sign. The 97-year-old matriarch, who still worked at Diamond until a few years ago, smiled ear-to-ear and you couldn’t help but notice that the pearl earrings and blonde locks on Miss Careful matched her own.


“She is Miss Careful,” Burton said. “They ran this place together forever.”

Taking over the family business wasn’t in Burton’s life plan, but when his father, Gary Burton, fell ill a few years ago, he moved back to San Jose from Southern California and took a crash course in the laundry and dry-cleaning business over a matter of weeks. He learned how to run everything from the industrial washing machines and old-school shirt pressers to the dry cleaning equipment and the massive mangle used to steam iron large items like sheets and tablecloths.

Nearly all the machinery is “vintage,” to put it nicely. Some of the old pressing machines are kept around to cannibalize for parts, and since working on old laundry machines is a rare craft these days, Jason Burton has started learning to fix things himself as well as he can.

“It’s all about the family,” he said. “This is about as blue-collar as it gets. But we also take pride in everything we do. We want to give our customers the best product we can.”

His sister, Janielle, who helped run the business until she started looking after her grandmother full-time, agrees. “When you work for a family business, you put all your heart into it,” she said. “It was exhausting, but, yeah, I miss it.”

Harold Hulbert originally opened Diamond French Laundry on Grant Street and dropped the “French” when the business moved to San Carlos and Delmas in 1950 (Interstate 280 runs over the original location). A widower, Hulbert married Mary Jane Burton in the early 1960s, gaining an instant family that soon became well-versed in the ins and outs of the business. Mary’s daughter, Rosaleen Burton Zisch, said everyone in the family worked at Diamond at some point or another, and she remembers Harold and her mom zipping off to dry cleaning conventions around the world.

The shop had four vans to provide pickup and delivery service to storefront cleaners in strip malls — and a Cadillac was a constant feature out front. Diamond survived the construction of Highway 87 The original billboard went up not long after and had at least three different looks in the ensuing decades. And interestingly, the current Miss Careful is the first time the image has had a face in more than 20 years.

The story goes that San Jose sign painter Norman Hollingsworth was touching up the sign in 1997 but died before he could finish Miss Careful. Harold Hulbert also had passed away that year, and Mary Jane Hulbert decided to keep it unfinished. And that’s the way it stayed until this year, when the diamond-shaped pieces on the sign were so badly deteriorated they were falling off.

Last fall, Dan Pulcrano, publisher of the alternative newspaper Metro Silicon Valley and a longtime Diamond customer, called Burton and said it was time to replace the sign. With Diamond footing the bill, Pulcrano used wood chips to get the original paint colors to match and got in touch with MESNGR to see if he would take on the painting job. Rainy weather forced some delays, but the job was completed by New Year’s.

With the sign finished, Burton plans to add more polish to Diamond Laundry, giving the Mid-Century Modern building a fresh coast of paint and fixing the smaller, freestanding sign in the parking lot. He knows it’s a lot of effort to continue a business in an industry that’s dwindled in an era of casual clothes and no-iron shirts. There are fewer smaller dry cleaners to contract with them as in the past, and most modern hotels do their laundry in house, now.

“I’m doing my best and putting everything I’ve got into it,” Burton said, adding that maintaining the quality without cutting corners — doing things the way his grandfather did like cleaning stuffed animals — is important to him. “Sometimes it comes down to pride versus economics, but that’s how I want to keep it. Otherwise, why do it?”

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