.There Goes the Neighborhood…Again

Last week, locals filled up Rollati Ristorante, a swank Italian restaurant across the street from San Jose City Hall, to celebrate the eatery’s final night after a short two-year run.

Rollati was the result of an all-too-familiar sequence of events. In the early aughts, as City Hall construction began to take shape, the politicos wanted to gentrify the downmarket riffraff across the street, including the legendary dive Lenny’s Cocktails at 171 E. Santa Clara St., plus another dive, the Quality Café. There was also a popular car wash and a few vibrant Vietnamese-owned businesses. In textbook San Jose fashion, the city wiped out the whole block and replaced it with a parking lot that sat empty for years.

In the end, Lenny’s was the bottom of the barrel—in all the right ways—so at Rollati, surrounded by people from the polar-opposite end of the social and economic spectrums, I sat there and contemplated the memory of Lenny’s and the endless births, deaths and reincarnations of this particular block.

The history of Lenny’s Cocktails is quite colorful. Hard-working Italians were involved from day one. Namesake Leonard “Lenny” Macchiarella opened the bar in January of 1958 with his partner Tom Vicario, a recently retired navy chief. Macchiarella had previously owned other joints, including Kelly’s Club on Monterey Highway and the Del Rey on Almaden Road. 

A few years later, Macchiarella sold the bar to Thomas and Sebastian Basile and Anthony Brigiotta. However, the name Lenny’s never left 171 E. Santa Clara St., while Macchiarella went on to operate several other establishments including a few bowling alley lounges.

In the mid-’60s, the San Jose Parks and Recreation Department oversaw an adult basketball program with many local businesses participating. One year, Lenny’s Cocktails had a team in the same division with Santa Clara Lumber, Southgate Liquors and a men’s store at 2nd and Santa Clara called The Wardrobe, whose team was led by John Arrillaga.

Unfortunately, throughout the ’70s, downtown San Jose deteriorated into a skid-row-style crime zone. In 1984, the Merc wrote a real estate article, citing a property with the lowest rent at the time, $280 a month, which included “the roar of buses, 24-hour insecurity and a view of Circus Adult Books, Lenny’s Cocktail Lounge, Minit-Man Car Wash, Open Door Christian Bookstore and women in bouffant hairdos and leopard-skin miniskirts.”

For years, a greasy-spoon dive called the Quality Café sat right next to Lenny’s. Around 1991, I remember breakfast tipping the scales at $2.99. By 2000, it had skyrocketed to $5.50. The dude behind the grill looked like Captain Lou Albano from the World Wrestling Federation. Pickled drunks stumbled out of Lenny’s at 8am and hit up the breakfast. Hungover twenty-somethings would roll in after a long night at the rock clubs on South First Street, ahem.

Then the San Jose Redevelopment Agency changed everything.

With City Hall slotted to relocate back downtown, the politicians wanted to remove the unwashed masses, so Lenny’s Cocktails needed to go. Around 2000, the city devised an absurd cockamamie scheme, which included a new symphony hall at Fourth and Santa Clara. It never came close to happening, but they leveled the whole northern side of the block and then waited for the next idea, which later turned out to be the Miro Towers.

At the time, George Rich owned Lenny’s Cocktails. After the city bought him out, he took the money and then bought the Caravan from Tommy Thatcher. Rich then passed away in 2011, after which I wrote a column in this very space.

Don’t get me wrong. I am sad that Rollati couldn’t make it work. There absolutely should be a swank restaurant near City Hall where all the politicos can congregate and hold court at the bar with lawyers, judges and newspapermen. Every real city has, or had, a place like that. Something else will surely emerge. I’m certain of it.

Yet the unwashed masses need somewhere to go as well. The entire concept of the neighborhood bar has mostly disappeared.

These days, even upscale restaurants can’t guarantee success in downtown San Jose. Rollati itself has joined the long list of places that exist only in memory. We will have to wait to see what comes next.