Some see it as a metaphor for life, this mind game where opponents shuffle 32 pieces around an eight-by-eight grid trying to checkmate the other's king.
The opportunities are endless, but nothing happens if you don't make a move.
When Stuart Vogel wanted to encourage community in central Auckland, where home is stacked into the sky, amenities are a mixed bag and traditionally unifying institutions such as a neighbourhood school don't exist, he turned to chess.
Three or four years ago, Vogel and a friend began playing the 500-year-old board game behind the big glass doors and windows of the Ellen Melville Community Centre in central Auckland or, weather permitting, outdoors in the adjoining Freyberg Square.
"People would walk past and think, 'What's going on here?' You'd get a lot of inquiries.
"There's the top down way of [building community], where the council or church provide funding and start something and hope people come. The other way is bottom up, where you just start playing outside and people see.
"Two becomes three, which becomes five, and eventually you're part of something bigger."
Auckland Central Chess Club now counts up to 70 adults of all ages and backgrounds and 30 children, all from apartment-dwelling families, as followers, has just joined the New Zealand Chess Federation and will next month host the North Island regional championships, Vogel said.
Hosting was exciting, but when it came to the club's reason for being, they were already mission accomplished.
"The idea was to create a community in downtown Auckland, and we have. And chess is the tool."
About 45,000 people live in central Auckland, broadly defined as the streets and lanes sandwiched between the State Highway 1 and 16 motorways, and running from the waterfront to just beyond the Queen St/Karangahape Rd intersection.
It's a space that's been under intense focus, as city leaders, planners, residents and business owners wrestle with challenges new and existing, including a lack of outdoor spaces near one residential part of downtown described as an amenity "wasteland" by a city advocate.
Covid-induced border closures, lockdowns and ongoing concerns have drained tourists, foreign students and - until recently - workers from the city, and Queen St reconstruction and City Rail Link works have proven endlessly disruptive.
Crime has also sparked concern, with some blaming the arrival in the central city of Australian deportees, gang members and people needing emergency housing for increased anti-social behaviour.
In August, police said assaults in the city centre had increased since the pandemic began.
Despite those challenges, thousands still choose to live downtown - and happily so, they told the Herald.
Lance Wiggs, his partner Su Yin Khoo and their kids aged 2 and 6, call home an apartment on the top floor of the Viaduct's Parc Complex.
"It's a beautiful place to live, a real piece of paradise in the centre of the city."
The medium density block was "very European" in style, with an enclosed green space for residents to share.
Other amenities, such as Victoria Park and Wynyard Quarter, were within walking and cycling distance, as was his work, favourite places to eat and shop and, importantly, people.
"I'm a venture capitalist and I'm a big believer in serendipitous encounters. And when you've got lovely spaces to go, you meet people."
Not everything was perfect - he'd love more outdoor markets and food options, fewer cars and more cycling and walking paths.
Hobson St in particular was hard to cross, and getting their eldest child to school at Freemans Bay Primary - on the other side of the motorway - was "quite terrifying", Wigg said.
More pedestrian-only spaces, including on Queen St, was "the dream".
"We've seen some of it, but we want to see more of it."
On the other side of Queen St Valley, Adam Parkinson is also happy with his decision to switch Sandringham bungalow for Emily Place apartment.
"I love it here. I'm basically living in a 15 to 20 minute city, I can walk to everything I need. And at times there's a lot of energy, and there's a sense of being amongst it."
However, as deputy chairman of the City Centre Residents' Group he knew some residents were missing out.
His apartment building was in a part of the downtown well-served by amenities, including a neighbouring square.
Others, especially in the Hobson and Nelson street areas, were not.
"It's the most densely populated place in New Zealand and there's nothing to step outside to. In terms of amenity, that whole quarter is a wasteland.
"We've [through the central city targeted rate] spent a lot of money at St Patrick's Square, Freyberg Square, the waterfront. But what about this area where we've got 20,000 people living?"
The mostly small apartments in Hobson and Nelson streets weren't built with families in mind, but were now being rented by single parents and migrants "because that's where they can afford to live", Waitematā Local Board chairman Richard Northey said.
"[They're] not great spaces for kids, because it's a fair way to Victoria Park … and they're just a bit too far away from some other quite nice places."
Myers Park, between Aotea Square and Karangahape Rd, had a good playground, and central city kids could enjoy the movies, theatre, art gallery and central library, but "we do need to be developing more leisure opportunities" for children, Northey said.
Planning rules didn't require developers to include outdoor spaces in new apartment blocks, but he and other city leaders would like to see incentives offered for doing so.
Another missing piece in the central city was a primary school, he said.
About 1000 children live in the central city, according to a Ministry of Education briefing he attended 18 months ago.
"A school is so important for the building of a community around it."
Auckland Central MP Chloe Swarbrick asked the ministry to buy the Kadimah School building after it was announced the Jewish state-integrated school was moving from its Greys Ave site, but was told it was too expensive.
The ministry were still looking for a site, as population growth projections in their long-term plan indicated the city centre would need a school, Swarbrick said.
One of the biggest challenges facing downtown was the "several lanes of pretty much motorway" in the middle of it.
"That's not particularly conducive to wellbeing in any suburb, particularly in a place where there's a large number of people in very close proximity to each other and are in need of more open public space and amenity."
Sydney pedestrianised large swathes of its main street - George St - at the start of the pandemic and it had been a "smashing success".
Auckland already had a good framework with Auckland Council's City Centre Masterplan, Swarbrick said.
The plan sets the direction for downtown as the city's "cultural, civic, retail and economic heart", according to its website.
But council-controlled organisations, particularly Auckland Transport, were "afraid of making changes" that were needed, she said.
"I feel very strongly that our city centre can be incredible if we not only live up to the vision prescribed in the likes of the City Centre Masterplan, but we also build these spaces that people want to be in, and will in turn make vibrant."
Two boys walking home were approached by a couple in a car and told to get in.