Rollati Ristorante opened across from San Jose City Hall and closed after a two-year run, with locals filling its final night. The restaurant emerged after early-aughts redevelopment that demolished dives, a car wash, and several Vietnamese-owned businesses to create a parking lot that sat empty for years. Lenny's Cocktails opened in January 1958 by Leonard "Lenny" Macchiarella, later sold to Thomas and Sebastian Basile and Anthony Brigiotta while retaining its name at 171 E. Santa Clara St. Lenny's also participated in local adult basketball leagues overseen by San Jose Parks and Recreation.
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.
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.
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