Lépine developed many buildings considered landmarks in Montreal, including the Olympic Village and Le Sanctuaire du Mont-Royal.
[10] Lépine started his first business at the age of 10, selling woodchips for fireplaces door-to-door at 10 cents a bag that he would pick up off the ground outside a timber factory in Lachine.
[10] At the age of 13, he dropped out of school to earn money for his family after his father became ill.[10][1] He worked at a jewelry factory and also started a flooring business.
[10] At the age of 19, he had $4,000 in savings, borrowed $8,000 from his local credit union and built his first real estate project, a single family house in Côte Saint-Luc.
[1][10] In 1969, Lépine and his business partner Lorne Webster purchased the 140-unit apartment building Tour Horizon at 1212 Pine Avenue in Montreal for $3 million.
[11] In 1971, Lépine and Webster wanted to purchase the Van Horne Mansion, adjacent to Le Cartier, and were planning a $7 million office building development.
In 1978, Lépine made his first real estate investment in the United States with the purchase of Drake Tower, a 143-unit apartment building in Fort Lauderdale, Florida.
[21] In late November 1981, Lépine started the development of Le Sanctuaire du Mont-Royal, a five building, 925-unit condominium, retail and athletic complex in Outremont, Quebec, the biggest project of his career.
[10] As was noted by the CMHC in 1989, Lépine's soaring sales were an exception to the lagging real estate market in Quebec during the same period.
[22][23][24][25] He announced his intention to develop a 67-unit apartment building on the property, originally named Le Cartier II, later changed to Sir Robert Peel, at a cost of $15 million.
[23][22] The move by the appeals court to grant a demolition permit on three historic buildings to Lépine was highly controversial and angered Heritage Montreal and Phyllis Lambert.
[28][29] Lépine planned to build a $2 billion mixed use project consisting of apartments, office and retail space on the site, which received partial pre-approval by the city of Montreal.
[29] Ultimately, Lépine bid $75 million, but did not buy the property due to weakness in the real estate market at the time.
[30][31][32][33] He was also planning a development called Canada Place, a 1,200-unit apartment project inspired by Le Sanctuaire du Mont-Royal in Moscow that was estimated to cost up to $700 million.
Lépine was financially backed by the Government of Canada, as well as from the Caisse de dépôts et placement du Québec and tenants who had secured office leases, including Samsung.
[citation needed] He was an official representative of the Canadian government and gave a personal tour of Montreal to a Russian diplomatic delegation that included Yury Luzhkov.
[37] Ottawa Mayor Jacquelin Holzman attended the official reopening of the building, renamed Horizon Tower, with Lépine in June 1997.
[44] As part of the deal, the Montreal YMCA agreed to invest $20 million to renovate and relocate to the Norris Building, adjacent to Lépine's new project.
[46] In 1997, Lépine entered public tender negotiations with the Canadian Department of National Defence to acquire a property they owned on Atwater Avenue, on the side of Mount Royal adjacent to Westmount, Quebec.
[47][50] However, the city of Montreal granted his zoning request and overwhelmingly approved Lépine's project, voting 7-2 in favour, in March 1999, shortly before closing on the property.