“The Shake Shack there?” asks the Grab driver when he sees I’m headed to Neil Road, the one-kilometre stretch of tar between Outram Park and Tanjong Pagar stations linking South Bridge Road to Kampong Bahru.

The Shake Shack is quite new, as are the artisanal coffee places and gyms (‘Kinaesthetic centres?’) that serve the residents of The Pinnacle@Duxton—a hulking presence in the background—as well as the busy folks zipping around the CBD (Central Business District). There’s the inevitable condo construction site, proclaimed by a banner that reads ‘Dream, Dine, Play’. I wonder if this is an instruction or a promise that buying a unit will make my life complete.

The crowing of roosters, their alarm clocks gone awry on this muggy, May afternoon, breaks my reverie. There are hordes of them, foraging for food on the grassy knoll in front of the HDB block just after the Cantonment Road junction. Why are roosters running amok in downtown Singapore? I resist the temptation to investigate further—pressing ahead towards the upper part of Neil Road, with its rich yellow and deep blue houses pressing back into a severe, cloudless sky.

This part of the road, informs a URA (Urban Redevelopment Authority) plaque outside one of these houses, was first developed when rich merchants moved away from the cramped lanes of nearby Chinatown. Among them was Choa Kim Keat (1858-1907)—of the eponymous road in Balestier, and Kway Mee Koo (1876-1940)—who built many of early Singapore’s roads and drainage systems. Just two doors down is Number 147—at one time the property of Lee Kuan Yew’s grandfather, where the boy Lee spent many of his days.

There’s a palimpsest effect at play here, the new inscribing itself on, but never completely erasing, the old—the 100-year St Matthew’s Church and Kindergarten opposite the restored shophouses has recently been appropriated for refurbishment and ultimately, absorbed into the expanded Police Cantonment Complex. Roosters apart, Neil Road is a microcosm of Singapore at large—development rubbing up against preservation, newness straining against antiquity.

It just happens to be named after one of the most monstrous English generals of the 19th century.