Santana Row 20th anniversary: A big gamble on San Jose that paid off

Santana Row will celebrate its 20th anniversary as the epicenter of consumer culture in San Jose on Monday. But when the swanky shopping center opened Nov. 7, 2002, it was far from a sure bet.

The opening of the $450 million, 42-acre destination had been delayed nearly two months after the largest fire in San Jose’s history destroyed one of its buildings that August. And only 34 stores and three restaurants were ready in time for the holiday shopping season.

Federal Realty Investment Trust had invested a lot in the mixed-use development, which was bringing together residential, shopping and dining, along with a hotel on the site of the old Town & Country Village. It was building across the street from Valley Fair, one of the hottest shopping malls in the country, and it was facing opposition from old-school San Jose boosters who believed it would put the final nail in the coffin for downtown retail.

San Jose’s Redevelopment Agency was pursuing a $1 billion project with New York developer Palladium to transform several blocks into what might have been a “downtown Santana Row,” but Palladium pulled out in March 2002. And remember that all this unfolded as the dot-com bust was melting Silicon Valley’s riches. Santana Row had the potential to be another Titanic — the ship, not the movie.

The guy who really believed in the project was Steve Guttman, Federal Realty’s CEO and chairman, but observers at the time said it cost him his job. Before Santana Row even opened, he had already stepped down as CEO and left the chairman post in March 2003 after a 22-year career there. He left the real estate business for the art collecting world.

In 2002, Guttman had moved to San Jose to oversee the project, and he and his wife lived in an apartment there. His vision was that it would be a place where people would walk around and grab a bite at a sidewalk cafe. “I want to hang out here,” he told columnist Leigh Weimers days before Santana Row opened. “I hope the rest of the city will embrace that.”

Guttman turned out to be right. People do want to hang out there — 13 million of them a year.

Its faux-European streets are filled with people, even on gloomy fall days, gawking at the Ferraris and Lamborghinis lined up outside the Hotel Valencia. It now boasts more than 100 shops and eateries and more than 1 million square feet of office space. The YWCA brought legions of high-heeled guys to parade at Santana Row instead of downtown San Jose in 2015, and San Jose Jazz has used it as a venue for its Summer Fest kick-off for more than a decade.

Live music concerts, makers markets and annual holiday events draw hundreds of people. Monday’s 20th-anniversary party should have a big crowd, too, for strolling, wine tasting and entertainment from 4 to 8 p.m. (Tickets are available for $50 at www.santanarow.com, with 100% of the proceeds benefitting Second Harvest of Silicon Valley.)

But, from where I stand, the secret of Santana Row’s success has come from an unexpected place. It’s not shopping; it’s all about the food.

As a shopping destination, Santana Row always has aimed for the luxury consumer — whether it was Burberry, Gucci and St. John at the start or today’s Kendra Scott boutique and Tesla showroom. But tastes change, and stores have moved in and out over two decades. What was once an Urban Outfitters is now a Hot 8 Yoga studio.

A stunning number of Santana Row eateries, however, have been in place almost since the start: Straits, Maggiano’s Little Italy, Cocola, Pizza Antica, Left Bank and Amber India are some of the oldest. As spaces open or new ones are built, they’ve been joined by hot newcomers like Momosan, Dumpling Time and Mendocino Farms. And that’s been a boon not only to Santana Row “shoppers” — who I’m not sure actually buy anything — but to the people working at the Splunk and NetApp offices.

None of this praise is meant to invalidate criticism that Santana Row is too plastic, too bougie, too whatever. It is what it is: a private development that can keep homeless or disruptive people off its pristine sidewalks, quickly clean up any graffiti or litter. Does it rain at Santana Row? Yes, but they’ll give you an umbrella if it does. Of course, all this perfection costs customers, residents and tenants a premium.

Where downtown San Jose may have signs for long-gone businesses like Zanotto’s, Voodoo Lounge and Firato Delicatessen on its buildings for years and maybe decades, once a business leaves Santana Row, it’s scrubbed away like it was never there. (Didn’t Roots + Rye used to be where Sauced is? I don’t know what you’re talking about. Gucci? Never heard of ’em.)

As for the charge that Santana Row finished off downtown San Jose’s hopes to become a significant retail destination, it’s hard to envision many of the upscale retailers choosing downtown even if Santana Row didn’t exist. High-end Japanese store Muji gave it a go in 2013 and lasted until it closed all its Bay Area locations during the pandemic. But one store doesn’t make a shopping destination.

The lesson that downtown San Jose needed to learn from Santana Row is that if you can create a critical mass of restaurants, you’ll draw a crowd. Look at downtown Campbell, which has seen a resurgence the past 15 years driven by restaurants and bars, not shopping.

But there’s hope for downtown yet. San Pedro Square has become a vibrant hotspot most nights of the week, with the wildly popular San Pedro Square Market and restaurant/bars like Farmers Union, Olla Cocina, District, the Brit, O’Flaherty’s and Dr. Funk. Sure, it helps if there’s a Sharks game and lunches aren’t great yet, but it’s a start.

If Santana Row teaches us anything, it might be that in 20 years a long-shot gamble can look like a no-brainer.

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