In 1991 Kiley moved to a new role as President of the New York construction company Fischbach Corporation. He briefly held the role of chairman too before moving again to become President and CEO of the New York City Partnership in 1995. From 1994 to 1998 he was also principal of Kohlberg & Company, a private equity investment house. Kiley's Transport for London biography notes that Kiley was also "Member of the Council on Foreign Relations, board member of the Salzburg Seminar, the American Repertory Theater, MONY Group Inc, the Princeton Review Inc and Edison Schools, Inc. He was on the Advisory Board of the Harvard University Center for State and Local Government". In January 2001 Kiley became Chairman of London Regional Transport (the public body appointed by the Secretary of State for Transport to run London's Underground network of trains), replacing Sir Malcolm Bates, and also Commissioner of Transport for London, the public body which reports to the Mayor of London and which has increasingly been granted authority formerly held by London Regional Transport. Kiley was given a $4m four-year contract, which was regarded as a strange bedfellow for Ken Livingstone, the socialist elected in 2000 as London's first mayor. Livingstone's and Kiley's views on London transport have proved very similar and both were opposed to the government's plans for public-private partnerships (PPP) to run the Tube. Kiley was sacked as chairman of London Regional Transport in July 2001 amid repeated clashes with his boss, Transport Secretary Stephen Byers, and was replaced by Malcolm Bates who returned to lead the organisation. Remaining as Commissioner of Transport for London, he and Livingstone took the government to court in trying to prevent PPP. They failed, and in January 2003 three separate private companies took control of maintaining various tube lines. In July 2003 powers for running the rest of the Tube network, including manning and maintaining the stations, was transferred to Transport for London and London Regional Transport became defunct. Kiley welcomed the opportunity to take greater control over the running of the Tube, but warned that he felt he would be hampered by PPP: "I maintain that the Government’s Public Private Partnership (PPP) is not the right way to manage the maintenance and renewal of the Tube. As they stand, the PPP contracts do not satisfactorily address the improvements to the Underground that TfL and the public demand. Nevertheless, we will do everything within our power to hold the infrastructure companies to account on those Tube improvements they have promised to deliver."