James Gomez has several years of involvement in Singapore politics through the Worker’s Party (WP). Although, Singapore is a dominant one party system, he nevertheless made the decision to participate in party politics for the following reasons. One, to lead by example and encourage young people to take the opposition party route to build democracy in Singapore. Two, to ensure ethnic minority representation is mainstreamed in Singapore’s politics.

He joined the WP in 2001 and was co-opted at his first central executive committee meeting as a cadre member and later as 2nd assistant secretary-general. In the 2001 general elections his (and his team mates’) nomination papers to contest the Aljunied Group Representation Constituency (GRC) were declared void as the statutory declaration forms were deemed to be improperly filed. (In 2005, the government amended the Parliamentary Elections Act to do away with the need for a statutory declaration.)

In 2003 and again in 2005 during the bi-annual party congress, he was elected as a central executive committee member and re-appointed as 2nd assistant secretary-general. He served for a period as chairman of the Policy and Communications committee. He contributed articles to the WPs' newsletter, the Hammer, and his most well known piece is "the New Poor" – the group of Singaporeans who find themselves financially and intellectually strapped due to the prevailing political climate and a saturated economy - which was the focus of debate in the 2001 general elections.

James feels that one of the most important challenges facing Singapore is to help the New Poor. He believes this will be one of the main concerns in policy-making for years to come.

In the run up to the 2006 general elections he was vice-chairman of the North-East Area Committee and advisor to the Northern Area Committee. During that time, he organized and chaired two public consultation exercises on the New Poor and Social Cohesion and the Casino Proposal. From time to time, he also initiated press releases ideas or spoke to the media on selected matters.

In 2006, he stood as a candidate for the Workers' Party as part of a five member team in the Aljunied GRC. James Gomez became the face of the 2006 general elections when the ruling party tried to make political capital out of his application for a minority certificate.

As a result, during Singapore’s General Elections held in May 2006, “James Gomez” became the most searched name in Technorati an "authority on what's going on in the world of weblogs". The volume of reportage in the local and international media on James Gomez during the nine-days of campaigning raised James’s profile to an iconic level.

The Workers' Party's Aljunied GRC Team polled 43.9% or 58 593 voters out of the 135 817 votes cast.