The showdown at the giant chess board was in full swing by the time Chris Riley arrived midday Saturday. Bursts of laughter and a Gipsy Kings playlist emanated from the white gazebo at Wooldridge Square Park, where old friends played with knee-high chess pieces that took two hands to move.
Riley had his wheelchair placed in a sunny corner. The warmth does him good.
“Hey, all right! How are you, man?” Riley said, lighting up at the arrival of a chess buddy he hadn’t seen in years.
The previous night, at a 60th birthday party that was expected to be his last, the former Austin City Council member and champion of Austin’s urbanist movement met one-by-one at his home with more than 100 well-wishers, a guest line that Riley kept welcoming even as his tired body needed to move to bed. Stage 4 cancer ravages his liver.
But here, the next day, this small gathering of friends playing giant chess at Wooldridge — here was a glimpse of Riley’s life’s work, the effort to make public spaces more people-friendly. And as with the rest of Riley’s causes, he hopes others will keep the venture going after he is gone.
“It was so fun to be able to come down here and set that up, and it just seems so right when you do it,” Riley explained Saturday, when I asked him: “Why giant chess?” He recalled how the spectacle of oversized kings and pawns drew the interest of people walking by the park or visiting the old library (now the Austin History Center) across the street.
“Like, once people see it, they say, ‘Yes, that is exactly what’s supposed to be in that park. It makes total sense,’” he said.
Riley started the giant chess games in the late 1990s, years before he became a Planning Commission member hearing zoning cases or a City Council member promoting protected bike lanes and more compact, transit-friendly housing options. Back in the 1990s, Riley was an attorney living a couple of blocks from Wooldridge Square — and one of the few thousand residents in downtown that had housed more than 10,000 back in the 1950s.
“It was like somebody had set off a neutron bomb or something. People were just gone,” Riley said. “I didn't understand why that would be, because it seemed like it's a wonderful, wonderful place to live, all these old homes. Why wouldn't people be living here?”
The desolate nature of Wooldridge Square at that time especially bothered him. Here was one of Austin’s first public parks — a popular spot for women's suffrage rallies in the early 1900s, the site where Booker T. Washington spoke to thousands in 1911 and later the launching pad for Lyndon B. Johnson’s 1948 Senate campaign — sitting lifeless. Riley would pick up litter at the park, but simply having a clean green space didn’t bring people back. Wooldridge needed an attraction.
After Riley bought the oversized chess set using $500 in donations, the Saturday matches took off in 1997 or 1998, and they drew a loyal following. Once Riley joined the City Council in 2009, however, it became harder for him to find the time to host giant chess.
He was still focused on the same mission: how to make public spaces more useful and inviting. Except instead of playing music and bringing coolers of water bottles to Wooldridge park, Riley was pushing to lift the downtown parking requirements, calling for making it easier to build garage apartments and championing a plan for a whole network of bike lanes.
Even in a city that boasts of its weirdness, Riley was a bit of an oddity: the council member living a car-free life.
“I remember Chris' early campaigns in Austin,” Council Member José “Chito” Vela told those gathered last Wednesday at a happy hour at Riley’s house. “The bike-riding council member. It was really just so visionary, so paradigm-shifting to be like, ‘Who is this guy?’”
Leah Bojo, who served as a Riley policy aide and now works with housing developers, added that 10-15 years ago, “Everyone thought we were crazy ... (but) Chris never wavered. He never paused and said, ‘Oh, maybe they’re right. Maybe we shouldn’t do it.’ He kept doing it, and he laid the groundwork for this (urbanist) movement that couldn’t have been laid without that persistence and clarity of vision.”
I should note that even now, most Austinites rely on cars. Bus routes and bike paths don’t serve all the corridors that people need. And while a proliferation of high-rises means downtown is now a vibrant home to 15,000 people — and more to come — the cost of that housing is out of reach for many of us.
But in the decade since Riley left office, Austin has moved closer to his vision. Voters in 2020 approved $460 million for sidewalks and bike trails, as well as a tax hike for the massive transit expansion known as Project Connect (although the latter is mired in legal challenges). Meanwhile, the City Council has updated its rules to allow more housing units on properties and to lift parking requirements for developments citywide.
Riley, who grew up in Tarrytown, sees all of this as progress toward Austin living up to its aspirations as an inclusive, environmentally conscious place. And he noted that the rapid growth of Austin, a city that has doubled in population every 20-25 years, is what gives the city fresh chances to do better, to make improvements we can see in our lifetimes.
“I had the opportunity right in front of me to help re-create the city and make it exactly what it aspired to be, which was just thrilling,” Riley told me Saturday. “Like, who wouldn't jump at that?”
The giant chess battle at the Wooldridge park gazebo continued as we spoke. Riley talked about the work that remains — from making streets more welcoming for bicyclists, walkers and street cafes to making more affordable housing accessible to more people.
“And best of all, we have this young crowd of people that are tuned in to all that stuff, that get it, that are motivated to keep working on all that stuff after I’m gone,” said Riley, at peace with his impending exit, whenever it may come.
The Austin skyline before him, a sunny afternoon of giant chess behind him, Riley wants the next generation to play on.
Grumet is the Statesman’s Metro columnist. Her column, ATX in Context, contains her opinions. Share yours via email at bgrumet@statesman.com or on X at @bgrumet. Find her previous work at statesman.com/opinion/columns.
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