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Bank towers are shown from Bay Street in Toronto's financial district, on Wednesday, June 16, 2010.Adrien Vecza

One of Canada's prominent corporate lawyers has retired from his firm after more than three decades on Bay Street, embarking on a new phase of a career that has included advising on many of the country's intricate deals.

Wednesday marked Clay Horner's last day at Osler, Hoskin & Harcourt, where he started as a summer student in 1982 and eventually spent 36 years.

During his time on Bay Street the legal world cycled through multiple phases of evolution. Despite the changes, Osler solidified itself as a top-tier firm. But the legal world continues to evolve and Mr. Horner is leaving the firm as the industry enters a new phase – one sometimes characterized as the 'end of Big Law.' Bay Street's 'Seven Sisters' used to dominate deal flow, but they now face sustained competition from large American law firms that operate here, and they are wrestling with wide-spread disruption of the legal world.

In the current era, commodified legal work can be outsourced to low-cost countries such as India, and clients can also access scores of information all on their own through digital services such as SEDAR, which compiles public corporate filings.

Mr. Horner specialized in mergers and acquisitions and his track record includes some of Canada's most interesting deals, including Imasco's going private transaction in 2000 and the Molson-Coors merger. Despite suffering a serious spinal injury during a skiing accident in December, 2011, he got back to work and later advised on Loblaw Co. Ltd's acquisiton of Shoppers Drug Mart and the purchase of Tim Horton's by a Brazillian private equity firm.

Most recently, Mr. Horner led Osler's team that acted as Canadian counsel to Blackstone on its acquisition of Thomson Reuters' financial and risk management arm.

Internally Mr. Horner was a leader of Osler's "first strategic planning exercise in the late 1990s, which helped the firm achieve a leadership position among Canadian law firms in the years that followed," according to a memo announcing his retirement.

He remains chair of Woodbine Entertainment Group and will continue to consult for select clients.

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