Members of the Chesterman family were living in 16 Cloudesley Square from 1921 right through to 1961.  They appear to have been a large Islington clan with ties to many other Barnsbury residents who no doubt played a central role in the social life of the area from the late 1800s until well into the 20th century.  Fortunately, they are well documented on Ancestry, with several splendid photos, and also appear in several Holy Trinity Church records of the time.

James Christopher Chesterman, the "patriarch" as far as 16 Cloudesley Square is concerned, was born to Cecil and Fanny Chesterman in 1877 in the infamous Beaconsfield Buildings. "The Crumbles", as this forbidding Victorian tenement building was affectionately and ironically known is now demolished.  It was built near Randalls Road off York Way as a model social housing development for workers and has its own website packed with colourful images and memories, here).  

By the 1891 census the Chesterman family is living in 82 Bemerton Street, which James Christopher shares with six siblings.  His father is an ironmonger's porter and the 14 year old James is already gainfully employed as an "Errand Boy, Post".

In 1902 James marries Jessie at Battle Bridge All Saints church and they stay together until James' death in Islington in 1951.  On September 18, 1907, there is a triple baptism of their three children, James Cecil, Arthur Albert and Ethel Jessie at Holy Trinity Church (see Ancestry family tree below).  They were then living at 84 Cloudesley Road and the father's occupation is recorded as Labourer. 

Then in the 1921 census James and Jessie move to 16 Cloudesley Square, where James, aged 44, is now a "Glazier (Pavement Lights)".  Pavement Lights are the flat-topped, walk-on skylights set into pavements to let light into the basement below.  There is a good example outside what used to be the bakery on the corner of Cloudesley Road and Cloudesley Square and it is tempting to speculate that James was responsible for this.  

From then through to the 1960s, the Chestermans remain at 16 Cloudesley Square together with a succession of colourful lodgers or co-tenants - see here to download details - many of whom appear to have become close friends.  The 1921 household included John and Alice Melvin (John was a wheelwright, and his father was a "Cat Meat Vendor"!) as well as Henry (Harry) Winter, a "Journeyman Tailor" and his wife Charlotte.  The Winters are still there in 1938 together with their son George "Barman.  Public House".  In 1928 we find James Chesterman as witness to the marriage of Walter Flowers, an upholsterer also living at No 16, to another upholsterer, Maria Griffith.  In 1931 he is again present at the marriage of his daughter Ethel Jessie, to Henry Hornsby, a newsvendor living at 34 Cloudesley Road (James is Henry's witness).  

James died in 1951 but his widow Jessie was still at No 16 in 1961 which she now shared with Charles Arthur Holland-Goodwin, born in a Workhouse! - see here for this amazing tale.  Previously, Charles' daughter Rose was living at No 16 in 1951 with her husband Cyril.

No doubt we have only scratched the surface of the amazing Chesterman family and their influence on the Cloudesley Estate and beyond, but for the time being, here are a couple of great photos (hover the cursor over the photos for captions).