Features & Columns

Silicon Alleys: Diamond Laundry's Iconic Vintage Billboard Is Finally Getting Restored

SIGN LANGUAGE: Thanks to the blessing of Diamond Laundry's retired proprietor, the beloved 'Miss Careful' billboard is in for a long-overdue touch-up. Photo by Dan Pulcrano

Miss Careful is being restored. What many claim is the oldest billboard in San Jose—that legendary sign on the Highway 87 overpass outside Diamond Laundry & Cleaners—shall soon return to life. As you read this, local artist MESNGR, who also helped paint the crazed VTA bus on the side of Alameda Artworks, is hard at work restoring Miss Careful to her old glory by painting a brand-new sign.

Everyone who's driven along San Carlos Street as it enters downtown for the last 70 years has noticed Diamond Laundry & Cleaners because, according to the sign, Miss Careful works there. And for the last few decades of those 70 years, many local connoisseurs of underbelly have offered to help restore the sign, especially in recent times as the sign had long since deteriorated beyond repair. But now, thanks to the blessing of newly retired proprietor Mary Jane Hulbert, a team of locals have banded together to make it happen. For many years, Mary was hesitant to allow anyone to mess with the sign, but just recently she finally changed her mind.

To get the skinny, I showed up not only for Miss Careful, but also to reacquaint myself with the Diamond Laundry business in general. Upon crossing the threshold and ringing a buzzer on the side of the counter, I spoke to Peggy Sutton, who immediately appeared and told me the building used to be a gas station pre-1950.

"That's why there's three driveways out front," she said, pointing to the parking lot.

The Diamond Laundry business actually dates all the way back to 1931, to an old location on Grant Street. Then in 1950 proprietor Harold Hulbert bought the property on San Carlos Street, where the business sits today. Hulbert passed away just over 20 years ago, but Mary, his wife, worked right up until recently, even into her mid-90s. Today, her son Gary C.H. Burton along with his children, Jason and Janielle, operate the place.

As I stood there, Sutton schooled me on the history. She told me about El Patio, the bar that used to sit next door, before Highway 87 existed. Soon after Sutton graduated from Piedmont Hills High School in the '70s, she bartended at El Patio before she was even 21. Decades ago, Pete's Bakery sat across San Carlos from Diamond Laundry. The guy who ran it was the brother of the guy who ran Dick's Bakery on Meridian.

And in the back, Sutton showed me around, pointing out ancient but still functioning industrial laundry machines. Three old-school washers, like the three wise men, sat there plugging away and refusing to die. An old "mangle"—a contraption with huge rollers and cogs for pressing sheets—still functioned, although not many people needed their sheets pressed anymore. I saw an old army dryer, plus huge tumblers, various steaming equipment and other machinery I couldn't identify. There was even an old boiler from the '70s in the back corner, the heart of the whole operation, pumping steam through various pipes to all the machines in the complex.

"Without that boiler, we're dead in the water," Sutton said. "We can't work. Everything is powered by steam."

Back at the front counter, an interior remodel was underway. A new era of Diamond Laundry seemed to be around the corner. All the ancient wood-colored paneling had been replaced. The walls were painted white for the time being. On the counter, I saw red Sharpies, receipt books, collar stays and rubber stamps. Customers came in every five minutes with their own personal requests. Peggy seemed to know them all.

When it came to the staff, people tended to spend their entire lives working at Diamond Laundry. One employee, Martha Rodriguez, recently retired after 38 years. A few current workers are going on 29 years now. It's not an industry to which people beat a path looking for employment. Most people are cringing for Google jobs instead, Sutton quipped.

"We don't get that many people walking in here wanting to work for us," she said. "So we're pretty honored that these guys are still here. Every person we use, it's hard to replace him."