Cuthbert Aloysius, the eldest son of James Domingo Shepherdson, was born on 18 October 1888 in Taiping, Perak, during the British Residential System. He had two brothers John & Henry and a sister named Pauline. Cuthbert Aloysius was baptized at the Church of Our Lady of Sacred Heart. Although he was a Eurasian, he had inherited some Chinese features from his mother, Teresa Peris, who was born in Shanghai, China.

During the time of his birth, history revealed that there were Chinese secret society clashes which presumably forced his family to migrate to Singapore in search of a better life. Assuming that he took the railway from Taiping to Port Weld (built in 1888), they probably came to Singapore around 1896-1898 by steamship as other modes of transport would have been impossible then.

Cuthbert Aloysius became a boarder in St Joseph's Institution. He was keen in boxing during his school days. Graduating in 1907 with a Standard VII education, he later worked for the Straits Trading Company as a clerk with a modest monthly income and rose to the post of a personal secretary to Sir John Wilkinson.

He settled down and married Mabel De Souza on 25 Jun 1910. Mabel bore him four children, Evelyn and Victor. However, Cuthbert's happiness was short-lived for they passed away at an early age. The surviving children of Cuthbert, Norbert and Anthony (Tony) became motherless when Mabel died shortly after contracting a certain illness.

Cuthbert had to rely on his sister-inlaw, [Grace Monteiro nee De Souza] to look after his children as he worked as a part-time stenographer with Raffles Hotel. In fact, his family lived quite comfortably with his late wife's rich sister, Grace at Serangoon Road until Cuthbert decided to get married once again.

He married Guilliermina Senhorinha Monteiro on 22 Jan 1921 and moved his family to a house in Bukit Timah. Not long after, the unfortunate Cuthbert became a widower once again as Guilliermina passed away from hemorrhage after delivering Mathew. Norbert and Tony helped look after their new sister and brother, Mary (Girlie) and Mathew.

Disillusioned from this sudden misfortune, Cuthbert Aloysius had to rely on two servants to do the domestic work and to provide maternal care for his children while he worked to support his family. A family friend, Mrs Gomes suggested that he re-marry so that someone could look after his children.

His concern over his children's welfare made him ask for the hand of Jesse, the youngest daughter of Mrs Gomes. His sons opposed strongly but that did not stop the marriage to Jesse.

Again, because of poor medical services, Jessie's first child (George) died at the age of only two months while her second (Peter) passed away when he was only 8 months old.

Cuthbert's problems were starting to be a burden to him. His small salary was hardly enough to meet the expenses of his large and growing family. Hence the services of his two servants were terminated. This made him a disturbed man. Although he was quiet by nature, his facial expressions failed to suppress his troubles and misery.

To ease the financial pressure, Cuthbert's late wife's rich brother, Reggie Monteiro offered to sponsor the education of Norbert and Tony. Initially, Cuthbert refused as he saw it his own responsibility to provide for their education. He nevertheless consented as he realised the importance of education. Wanting them to be educated and well mannered, Cuthbert allowed the two boys to live with their uncle.

The Story Continues...