Of the three San Francisco buildings designed by architect Jeffrey Heller now under construction, the one that fascinates me the most isn’t the 57-story tower or the 19-story high-rise.

It’s the five-story office building on the edge of Chinatown, a cleanly detailed glass box at 500 Pine St. that shows how convoluted the politics of development can be. How architectural values are as faddish as anything else. And why empty lots can sit empty for decades, no matter how prime the location.

“I’ve worked on this corner off and on for close to 20 years,” Heller said while we explored the compact box, which should be completed next month. “It’s probably the most complicated approval I ever did in my life.”

This is no casual statement: Heller Manus had a long run as the go-to architecture firm to get something built in and around the Financial District. That ended when Heller’s efforts on behalf of a developer to erect a 38-story tower next to the Transamerica Pyramid was torpedoed by the Board of Supervisors in 2010.

But the firm is back in the limelight as the local affiliate of England’s Foster + Partners on the recently approved Oceanwide Center, which will include a tower at 50 Mission St. higher than the Transamerica Pyramid. Heller also designed 181 Fremont St., 57 stories of offices and condominiums that opens next year and will top off at 800 feet.

Which is a far cry from 500 Pine — four stories at the corner of Kearny with a discreet penthouse at the back, nestled on two sides by a parking garage and topped in part by an extension of Chinatown’s St. Mary’s Square.

The snug profile is also a far cry from what was proposed here in the early 1980s: a 30-story hotel tower to be erected by Walter Shorenstein, then the city’s largest developer. After all, the neighbor across the street is granite-clad 555 California St., 779 feet tall and still a skyline summit.

A decade earlier Shorenstein surely would have gotten his way. But the tower proposal clashed with San Francisco’s 1984 ordinance to protect public parks from new shadows. Also, Shorenstein was feuding with City Hall over his lawsuit against development fees imposed to help fund Muni.

Other tower proposals at the time were allowed to go forward. Not Shorenstein’s.

“Now, our inclination is to do nothing,” was the developer’s response. The corner went into limbo as a trash-strewn vacant lot.

Fast forward to 1999, the crazed peak of the dot-com boom, and Shorenstein Co. hired Heller to jump-start 500 Pine and another problematic site a half-block away: 350 Bush St., where the shadow ordinance and the historic shell of the San Francisco Mining Exchange had hobbled plans for a tower.

Heller — described by former Examiner and Chronicle reporter Gerald Adams in an article at the time as someone “who studies downtown zoning restrictions the way fishermen study tides and currents” — crafted a scheme where 350 Bush would hold a 19-story tower shaped so as not to overwhelm the back of the 1920s classic Russ Building next door. Meanwhile, 500 Pine wouldn’t peek above St. Mary’s Square. The roof would hold new park space, helping to satisfy 350 Bush’s open-space requirement, and the two projects would be built simultaneously.

The pair were approved in late 2000, just in time for the boom to go bust. Shorenstein Co. sold the sites to Lincoln Property Co. just as the 2008 recession hit. Finally, last year, construction began on both.

Two visions of 500 Pine St.: the building as it was designed in 2000 and a rendering that shows the design now under construction.

Two visions of 500 Pine St.: the building as it was designed in 2000 and a rendering that shows the design now under construction.

Here’s another wrinkle to the tale: 500 Pine’s current look bears no resemblance to the 500 Pine that was approved in 2000.

Back then the safe road to approvals was to wrap your building in familiar garb, so Heller adorned the walls with punched-window masonry that aped — sorry, “paid homage to” — nearby older structures on Kearny. The corner wore a rounded bay of green metal posts that fanned out at the crown.

“This was our big, bold statement,” Heller said last week, laughing. “The whole thing for us was that buildings should be very contextual, very literal.”

When the economy revived in the current boom, Heller kept the approved dimensions but scrapped the old-time ambience. Visit the corner now and you’ll see seven deep, tall bays, huge panes of glass framed by silvery-gray steel. The first-floor storefront alternates glass with muted beige limestone.

Personally, I’d have gone with a richer stone that contained the bays below a solid cornice — define the corner rather than have the vertical bays collide with a parking garage of note only for the neon sign above the Kearny Street entrance. But the strong vertical rhythm fits with Kearny’s established character, and there’s a satisfying sophistication in how the metal meets the glass.

Picture a well-tailored suit of the sort now rarely seen in the Financial District: somber and stylish and crisp.

After talking with Heller, I called Dean Macris, the city’s planning director during the original showdown with Shorenstein. He views the outcome as worth the wait.

“The result is the right scale, don’t you think?” Macris said. “This was a classic case of where high-rise development needed to stop and neighborhood amenities needed to start.”

This time next year, I’m guessing that the new corner of St. Mary’s Square will be a popular lunchtime destination. Visitors will soak up the sun and take in the views. They won’t care about the backstory. That’s the way of cities: A handful of people fight over the details, and the rest of us live with the results.

Place is a weekly column by John King, The San Francisco Chronicle’s urban design critic. Email: jking@sfchronicle.com Twitter: @johnkingsfchron