“The Doom Loop “- Walking Through Downtown San Francisco

Downtown San Francisco, we are told, is in a “doom loop”. You probably have heard. Everyday, the San Francisco Chronicle, publishes the latest report on employers leaving downtown, retailers closing their doors, wasted public money on poorly managed programs (2 million dollar toilets!), the latest staggering statistics on homelessness, and so on. And if you didn’t hear it there, the national press loves these stories, Exhibit A on liberal governance run amuck. As always,, I like to the think the true story is buried somewhere underneath the headlines. To wit, recent walks through all of San Francisco have found the vast majority of the city every bit as vibrant and wonderful as ever. But unfortunately, the reporting on the center part of town seems to be an accurate chronicle of Downtown. And its not pretty.

So when I heard the term doom loop, I thought…. that would make a good walk!. So this walk takes one through two parts of downtown San Francisco; the financial district (mostly office) and the edge of Union Square (mostly retail). And yes, the street-scene was at times depressing, the missed opportunities of San Francisco’s horrid planning infuriating. But rather than endless photos of empty storefronts (and there are plenty) I thought I’d try at least to focus mostly on what’s there, “the bones” if you will, and opportunities- both missed and potential. Here’s the route:

Coming To The City

If you live in a metropolitan area, you have some relationship with a downtown. Perhaps you work there, or go to cultural or sporting events there, attend parades , or shop. And it can be exciting, its different from where you live. As a kid, trips downtown were always a special event, even if it was just a trip to the department store for clothes. And years later, working downtown, while at times a grind, still had an undeniable buzz, up to and including the buzz one often caught after work at a nearby bar.

I opted to come into San Francisco, from home in Berkeley, not on BART, but on a Transbay bus, which allows one to arrive at the spectacular Salesforce Terminal (1), perhaps the world’s most expensive bus station. This terminal, which replaced the previous aging bus terminal, is located to suit these busses, but little else. This is the Thursday morning rush hour:

Salesforce Terminal – Pelli Clarke Pelli Architects (2018)

It is not connected to incoming rail at this time, its not even connected to BART or Muni rail. Instead of figuring out how to bring electrified commuter trains downtown from 4th street, and likely Muni with it, the city separately built the second most expensive subway per mile in the country 3 blocks away, which travels 1.7 miles. Not surprisingly that line is not delivering expected ridership. It just seems like a missed opportunity, while acknowledging the challenge involved, to have tied all this together. One has to admit much of the “public works” San Francisco has developed in recent years have yielded largely over-priced, underutilized, and/or ridiculously behind schedule projects (Van Ness Rapid Bus comes to mind) . Too many times in my 30 years here, San Francisco just shows throws good money after bad. Just today, there was an article explaining that a process to select new public trash cans for the city is on hold because they suddenly realized the design would be vulnerable to graffiti. 32 months have passed since the city selected 3 prototypes before landing on the current choice. These are trash cans.

To be fair, the city’s master plans have yielded stunning new mixed use neighborhoods in Mission Bay and Rincon Hill. And the best part of the terminal is the rooftop park, which I profiled previously, and is a terrific public amenity , a unique destination. And exploiting unique one of a kind destinations has to be part of downtown’s future. But the focus today will be down on the street.

Salesforce Park

Financial District

L-Crown Zellerbach Bldg- SOM Architects (1959), C-Shell Bldg – George Kelham (1929)

Exiting the terminal , I walk to Market Street. I live in Berkeley now, work in downtown Oakland, but for many years worked downtown, living walking distance away. But one constant in my over 30 years in the Bay Area, in fact my longest relationship here, is with……….my dentist. How many hours I have spent on the top floor of that brick building on the right, getting scraped , or drilled , or lectured., all the while putting the dentist’s son through grad school. The one saving grace was a view down to this corner, where I could regard these buildings while strapped in my chair waiting for the bad news. And down below, the Crown Zellerbach Building , from 1959 on the left, and the elegant Shell Building, from 1929, in the middle. An anaesthetized architect who doesn’t apparently floss enough top floor on the right.

This pair a graceful testimony to early and mid-century densification of downtown San Francisco. The Shell Building respectfully anchoring its’ corner, and Crown-Zellerbach resolving its triangular lot in a very modernist way, a tower, a plaza, and a circular retail folly. This was San Francisco’s first International Style curtain wall, ala the Seagram Building in New York. Standing at this corner, one can’t regard the Crown Zellerbach building without thinking of the time it was born, the late 50s, the apogee of High Corporate Modernism. Most downtowns (San Francisco an exception) would begin a decline not long after.

And so this is as good a place as any to consider the state of the endangered downtown office worker, or if you will, their roll in“Post-Corporate Modernism” .Reasons why San Francisco has not been recovering like the other downtowns are well documented. It goes like this.: first, tech-heavy downtown SF has been and continues to be more remote than other locations. Second, the Bay Area’s more lengthy pandemic mandates made it both harder for businesses relying on workers to survive a longer period of vacated workplaces, and added to fixing in place a hybrid work, where other cities have seen more of a return to the office. And third, while worker foot traffic has decreased, the resulting percentage of that foot traffic that consists of “troubled individuals” has increased, and with that, the perception and reality of a place that seems, and may be, less safe .

I too am one of those newly-minted part-time downtown workers, splitting time between home and office. And I have liked the arrangement, I like the buzz of the office, and like too the generally more productive time working from home, particularly when I am creating. And while we are increasing our in-office requirement from 2 to 3 days, the hybrid schedule is here to stay. There just will never be the same number of people working downtown, at least in the Bay Area.

I arrived at California Street (3). With its iconic vista up Nob Hill, its wider right-of-way, and of course, the cable cars, California always been the most pleasant of downtown streets to me. I used to commute from Nob Hill, walking down here to work, and then jumping on the cable car back up at the end of the day. Being able to walk to work is a great thing, and the commute home on San Francisco’s cable car for locals was terrific.

Nearby was the iconic Tadich Grill. With a line outside, I was reminded that people will always come to unique destinations, always a crowd at the Tadich Grill, where little has changed. in 150 years. This place is a good fit for downtown, another classic one of a kind institution.

From California , en route to the Transamerica Building, I passed the Embarcadero Center. Built in the 1970s, this mixed use multi-level urban shopping promenade has held up well (4) . I’ve always appreciated its quality materials , particularly the paving , and the way it managed to draw you into a mid block arcade that would periodically open to the sky, and lead you up to raised walkways via playful spiral stairs. All of this helped to render a largely brutalist structure user friendly. Needless to say, as an outdoor downtown shopping mall, the complex is hurting, though many of the shops are hanging in there. The upper level walkway is a desert, at least on the day I was there.

This stop was en route to the Transamerica Building, and specifically the adjacent Redwood Park (5), one of downtown’s first Privately Owned Public Open Spaces (POPOS), (as is the Embarcadero Center above). I worked for several years right next door, and found it a little slice of paradise, a zen reprieve from periodic madness of an Architecture office. It also offered a unique perspective on the pyramid above. POPOS are one of downtown’s best features, existing both as street level plazas and most gloriously, roofs terraces offering stunning views of the upper reaches of nearby buildings. I looked forward to visiting the park on this day, but that was not to be. The park was closed as part of the Transamerica Bldg renovations. I couldn’t shake the doom loop.

South from the park, the walk along Sansome offers a string of handsome buildings, including the Bank of California(6), at Sansome and California. one of many “Temples of Finance” downtown. When I first moved to San Francisco, I opened my bank account at another downtown bank, another “temple”, after I had secured a job. I entered the ornate hall, and at 26, thought this might be a good place to stash my riches. I was a bit intimidated- what if they found out I only had $77.00 to my name. Nonetheless I felt like a prince, spent far too much time selecting the design on my new checks (stagecoach or snow-capped peaks), signed on the dotted line, deposited my $77.00, and that was that. Such a moment should be made concrete in a Banking Temple such as this. I chose the stagecoach.

Bank of California Building- Bliss and Faville (1908)

Downtown is indeed about money, and the banks went out of their way to display it. Nearby sits Chicago master architects Burnham and Root’s Merchants Exchange, who were joined by Julia Morgan on the design. The entry lobby is luxurious, and the tower court set-back above allows for the skylight., a rare thing. It feels like a train station.

Merchants Exchange Building – Daniel Burnham, Willis Polk ,Julia Morgan (1904)

But what of the future of such spaces, they too, it would seem, might be endangered. Our neighborhood has lost multiple branch banks the last few years. Is the banking temple doomed, and if so, how are they transformed ? In fact , many already have been. A block away at Sansome and Pine, one finds two splendid buildings across the street from one another. On the south side sits the former Pacific Stock Exchange(7) and tower, seen here.

Pacific Stock Exchange- Miller and Pflueger (1930)

The stock exchange , another temple of finance, is a fusion of the traditional classical vocabulary chosen for these financial institutions, but infused with art deco, which one can see at the tower entry, the sculptures, and the magnificent tower interiors. So this former Temple of Finance, with its vast interior, has been reborn…….as an Equinox Gym. So yes, where stockbrokers once flailed their arms with orders, occasionally grabbing their heart. Now stockbrokers flail at punching bags under the watchful eyes of a personal trainer…..still I assume grabbing their heart.

The adjacent tower is vintage art deco, and includes the marvelous 2 level,-City Club, and includes Diego Rivera’s fresco at the magnificent connecting stair between the two levels. It is another classic institution.

Meantime, the compact Royal Insurance Building across the street is a great example of turning an older, smaller office building converted into apartments. Its been around for awhile, in fact before moving to Berkeley, we looked at an apartment here, and briefly considered moving downtown. For us , our lives shifting across the Bay made it less viable. But to live a modest walk to nearby work, and not own a car would be attractive, not to mention having the only front door in the city with a unicorn overhead.

Royal Insurance Building – Howells and Stokes (1907)

One of the most often cited hopes is that these half filled office buildings can be turned into much needed housing. In the best case, this can really only work in some of the buildings. Floor plates can’t be too big, windows need to be retrofitted to operate, mechanical systems must be replaced. And then of course the tenants that ARE there on leases can’t just be kicked to the curb. But there are studies underway, and several recent examples of bldgs large and small, such as the Royal Insurance Bldg., that have turned to residential in San Francisco. In the city where I grew up – Syracuse NY, half of its old downtown buildings have turned from office to residential over the course of 30 years, turning a half-deserted downtown into a vibrant mixed use neighborhood.

But it brings to mind another budding question, what will that future demand look like? A recent study has shown recent college graduates are increasingly drawn to smaller metro areas, rather than the largest and most expensive cities, like New York, LA, San Francisco.

Courtesy New York Times

I grabbed a coffee at a coffeehouse in the Mills Building on Bush and Montgomery. Beyond the beauty and the jobs, many who migrated to San Francisco in the last century were drawn too by lifestyle, a place where you could be yourself, find your tribe. You put up with the cost, because living in Omaha or Syracuse wasn’t an option. But in 2023, that’s not a driving factor anymore. So maybe this is all a good thing, reducing the pressure on housing? I remember as recently as 2019 coming into downtown and thinking the sidewalks are too damned crowded (and also thinking I had lived in Berkeley too long).

San Francisco has always been a boom and bust town, and since I have been here there was boom in the late 90s, then a bust, then a boom in the 00’s, thenthe “great recession” and then another boom. Is this just another few year bust, to be followed by another boom, maybe led by a resurgent AI fueled tech industry? ( I imagine in 2027, downtown cafes now filled not with solo freelancers and their laptops, but just the laptops, chat-bots conversing with one another about where to get the best bagel in San Francisco). This feels deeper, the basic structure of how the metropolitan area functions is shifting.

Well, at least on this Thursday morning, downtown felt busy, and the cafe was full of actual humans. Next door , Burnham and Root’s substantial Mills Building entry, a white marbled signature of this Chicago’s firms work ,never looked better. The doom loop faded away.

Mills Building – Burnham and Root (1907)

Spaces In Between en route to Union Square

One could make a case that, aside from topography, one of the things that gives San Francisco its unique character are the “spaces in between”. Hillside stairways, small SOMA side streets, narrow Mission lanes, and yes, downtown alleys. These are the heart of the city. The scale of these places are intimate, quiet, and in sharp contrast to the hub-bub that exists at the end of the lane. The most well know downtown would be Belden Place (8), lined with restaurants.

Belden Place

There is a web of these downtown alleys with handsome 2 and 3 story buildings. Similar to Chinatown, maybe downtown alleys such as these can be networked together in some identifiable whole, pedestrianized , greened up, linked as a whole, with more active uses in some of these attractive spaces. Spoken like a true planner.

Commercial Alley

The alleys include little delights, like this old PG and E substation, currently for lease.

PG & E Substation J- Frederick Meyer and Henry Vensano (1914)

Union Square

Across Kearny, we come into Union Square proper. The blocks around Grant Street (9), east of Union Square, are chock-a block with elegant retail buildings. This area contains some of San Francisco’s finest retail buildings, both restored and completely reborn. At street level, luxury retail, and above, hair salons, galleries, and other uses bathed in light from extra large windows. I recall I once was convinced that I should get my hair “done” at a third floor salon called Architects and Heroes, because, of course.. I came out looking like a poodle, and considerably poorer. I’m a simple guy, and retreated to my humble Mission District barber for repair work. I like this pair, which speak to the renewal of a neighborhood’ fabric. The building in the left 100 years old but reclad as a glass box. The upper floors of the old buildings would make great apartments.

And a block away the old hulk of Macy’s

Has been reborn:

100 Stockton- Gensler Architects (2022)

And of course, from mid century, Frank Lloyd Wright trying out his scheme for the Guggenheim in miniature, the mid-century Morris Bookstore (10) with its spiral ramp to the top. With an entry that recalls the Mills Building, the design remains stunningly fresh on yet another alley.

Morris Building – Frank Lloyd Wright (1949)

You’ve probably noticed in these photos something, where are the pedestrians? Now, this was a Thursday at 11am. But it was pretty deserted. And that is the segue to the inevitable vacant storefront photos- they are all over Union Square.

In a twist, some retailers who were priced out of Union Square now see an opportunity to locate there, so that’s something. But in the meantime, we are left with a lot of emptiness. Best not to think of the bustling old days of 2019.

In Union Square’s current underpopulated state, one becomes even more aware of the many in need. This scene plays out throughout the city. Below, a woman inched up Post Street, in front of the Burberry store, her life stuffed in 5 shopping bags.
I helped her to a bench in Union Square itself, and thought, what’s next for her ? To be sure, San Francisco does not have the market cornered on this heartbreak, it exists in every American city . But that’s no comfort. The doom loop was back in force.

Moments after helping the woman to her new bench, I ducked inside the pristeen new Central Subway Muni Station at Union Square (11), this the subway line I spoke of at the top. The genesis of this line was born after the ’89 earthquake, design began in the 90s, was supposed to be completed 5 years ago, and finally opened earlier this year. It cost 1 Billion dollars per mile. That’s Billion, triple the original estimate.

MUNI Union Station Station (2022)

My eye was drawn first to the art installation above, then to the only other person in the entire station. He was missing the art! And I missed the point of all of this. To be sure , this new line has made getting from Mission Bay to downtown much easier. And the Chinatown Station does have some great art. But again, it just seems for the money spent on this AND the Transbay Terminal, much more could have been accomplished.

I returned up to Union Square, and the woman had fallen asleep on the bench.

It was lunchtime , and I headed down Post, to the penultimate stop on the Doom Loop. And what better stop…than a bar, and not just any bar, but the Pied Piper in the Sheraton Palace Hotel (12). Downtown still with ample supply of them, offering a quick fix after a tough day. Lord knows I spent too much time sampling downtown’s offerings , and the Pied Piper was always the upscale counterpoint to Sutter’s or the much missed Ginger’s Trois.

“The Pied Piper”- Palace Hotel (1909)

Ahh, the downtown bar, where workers can steel themselves for the commute home (hopefully on transit) with a couple of stiff belts with co-workers. And belts were rarely stiffer than a few of this place’s manhattans or martinis. A day of stress would melt away, and the famous namesake Maxfield Parrish painting, seen above, could, depending on the number of cocktails, take on a life of its own. Another classic downtown institution providing a valuable service to commuter and tourist alike.

The loop was nearly over, and although not imbibing, I felt restored by the Piper, as always. Across the street, I made one final stop, up to a “POPO, the roof deck at One Kearny (13) , where one can sit and admire the skyline hard against the silhouette of the historic neighbor. This a secret spot, but much to my surprise, a group of women were on a sketching outing. They had chosen well. The foreground full of detail, and in the background, the new skyline, Salesforce Tower, the tallest building in the distance , marking where we began. We chatted at length.

One Kearny – William Curlett (1906), Charles Moore (1963), Charles Bloszies (2009)

There is no shortage of hand wringing about what can be done to help downtown. Meetings convened, plans floated, temporary solutions (more pop ups!) proposed. Where to begin. Certainly, the city must find a way to more effectively deal with the homeless and drug epidemic on its streets. None of this will matter if that doesn’t improve. But can it? Its been an issue for all of my 35 years here, and it is now much worse. Transit systems will have to deal with the new budget realities that weekday commuting numbers won’t come back (but weekends have, and service should reflect that). It is encouraging that the extravagantly byzantine City of San Francisco Planning Department has proposed revising codes to make it easier to add residential in downtown buildings, and expedite permitting.

The much respected San Francisco Bay Area Planning and Urban Research Association (SPUR), has offered up its ideas- four areas of focus for advocacy:


My very first trip to San Francisco was in 1985, 38 years ago, as an Architecture student for the American Institute of Architects’ annual convention. An architect I had studied extensively had designed an addition for this same building where I now stood. It had a tiny porthole with a view of the 1985 skyline. Someone took a polaroid of me ,a tiny face 12 stories up, the photo now long gone.

Much of what I saw today did not exist then, or had long since been demolished. There was the grimy old bus terminal, a freeway that cut off the Ferry Building for the city. Yerba Buena was a plot of dirt. Mission Bay empty fields. A whole new city downtown grown up to the south.

So, standing on a roof terrace , coming full circle from 1985, I suppose this is where I make an eloquent soliloquy about how San Francisco rebuilt itself a century ago, and gosh darn-it, it will again. Well, I will remain cautiously optimistic. There is a wealth of creative energy here, a wealth of innovators, and well, wealth. Can policy makers in San Francisco learn from past mistakes, and get smarter in how they approach the needs of the City? We will find out.

Just like the new city seen from this roof deck, which took decades to develop; change will come slowly. And in some ways , its more complicated. Instead of a blank slate, it involves rethinking downtown’s fundamental role in the metropolis.

So yeah, Cautiously optimistic. Much patience required. A first test : let’s get those new trash cans deployed. .

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