The premises of London Life, London's own home-grown insurance company, were built in 1927 in a Neo-Classical Revival style. A.O. Jeffery, president of London Life at the time, laid the cornerstone of the company's Dufferin Street head office in 1926. Fittingly, the London Life premises were erected on the site of the home of the late Sir George Gibbons, who was a founder, a director and a board member of the organization for many years. Sir George Gibbons's widow, Helen, moved into another listed building at 477 Waterloo Street after she left the Dufferin home so that it could be demolished. The chosen site for the new headquarters met opposition by the City Council, which felt that commercial enterprises should not intrude on the main park. Council apparently came around once it became known that the company was seriously considering offers to relocate outside of London.
Specializing in financial and commercial law, Sir George Gibbons was one of London's leading legal figures. In 1896 he established the London and Western Trusts Company Limited and became its president. Gibbons also helped found the London Club and the London Hunt Club. He also sat on the original 1908 board of governors of the Western University of London Ontario. Gibbons is remembered in London through Gibbons Park. Appropriately, this park borders the north branch of the Thames, a river that eventually finds its way into boundary waters. Gibbons was famously involved as a diplomat in the Boundary Waters issue with the US. The Gibbons family is also remembered through Gibbons Lodge, home to his daughter Helen Beresford Gibbons. This house was bought by the University of Western Ontario in 1961 and has served as the residence of the president.
The London Life premises had started out in the Ontario Loan and Debenture building at the market. After 1906, London Life moved to 424, Wellington. The Ontario Loan and Debenture was taken over by Royal Trust in 1968 and the building on Market lane was demolished in 1971. When the 1927 Beaux Arts building opened, it had a staff bowling alley, a print shop, and a pneumatic mail collecting system. Most of the walls were coated with a special plaster to absorb the sound of the many typewriters and adding machines in use. It is rumoured that the best-looking girls of the city all worked at London Life, and during lunchtime many young men would wait outside the premises in the hope of meeting them. In the lobby of the building at 255, Dufferin, one finds the only coffered banking hall ceiling left in London. Although the left wing of the building was completed by 1927, the ring wing was not added until 1949. The postwar addition at the back of the building was carefully designed to echo the original structure's lines. 255, Dufferin today remains a monument to one of the city's greatest financial success stories.