Portillo returned to the House of Commons after winning a by-election in 1999 for the constituency of Kensington and Chelsea. He then started to re-think many of his ideas and began to argue for a more socially liberal Conservative Party. He became the Shadow Chancellor of the Exchequer in February 2000 but he did not have a good relationship with party leader William Hague. He was a candidate in the 2001 Conservative Party leadership contest; he lost to Iain Duncan Smith. Portillo left the House of Commons at the 2005 General Election and has since hosted several television and radio programmes.