Having started his legal practice in 1971, de Silva was active in politics from his student years, having started the Sri Lanka Freedom Party Law Students Association. He supported Sirimavo Bandaranaike in her campaign in the 1970 general election. He travelled to the United Kingdom in 1975 and qualified as a solicitor. He returned to Sri Lanka in 1978, and assisted Bandaranaike in her defense against the Special Presidential Commission appointed by President J. R. Jayawardene to investigate allegations against Bandaranaike for abuses of power during her tenure as Prime Minister.[4]
On 4 July 1996, De Silva escaped with injuries in an attempted assassination by a LTTE female suicide bomber at the Stanley Road in Jaffna. This incident took place minutes after the Minister declared open a branch of Building Materials Corporation (BMC) in Jaffna. Brigadier Ananda Hamangoda (Jaffna Sector Commander), Ranjith Godamuna (Chairman, Lanka Cement) and 21 others were killed with more than 50 injured in the explosion.[6]