A Legacy of Innovation: The History of The Hill Companies
The Hill Companies are a fourth-generation family enterprise based in Regina, Saskatchewan, that has left an undeniable mark on North America's business landscape. Founded in 1903 by Walter H.A. Hill and E.A. McCallum, McCallum Hill & Company initially focused on real estate development and insurance. Over time, the company would expand its operations and diversify its interests throughout Western Canada and the United States.
1903-1908
Building a Foundation
1903
From modest roots, The Hill Companies have grown into a formidable force across North America. The journey began with visionaries Walter Hill and Edgar McCallum, who established McCallum Hill & Company with a focus on real estate and insurance. Their unwavering belief in the province’s promise and their ambition to forge a business epicentre in the prairie heartland propelled them to swiftly acquire land, setting the stage for residential and commercial growth.
From modest roots, The Hill Companies have grown into a formidable force across North America. The journey began with visionaries Walter Hill and Edgar McCallum, who established McCallum Hill & Company with a focus on real estate and insurance. Their unwavering belief in the province’s promise and their ambition to forge a business epicentre in the prairie heartland propelled them to swiftly acquire land, setting the stage for residential and commercial growth.
1903
In a bold first move, the company acquired farmland in south Regina, overcoming the owner’s initial hesitance with a striking $20,000 cash offer. In an era where the one-dollar bill was the sole legal tender, Walter’s determination was evident as he carried a briefcase brimming with 20,000 bills, ready to secure the deal. The first purchase sparked a pivotal moment, as the duo then flipped the land to the government for the construction of the esteemed Provincial Legislative Building—a landmark deal that showcased the duo’s flair for persistence and opportunity.
In a bold first move, the company acquired farmland in south Regina, overcoming the owner’s initial hesitance with a striking $20,000 cash offer. In an era where the one-dollar bill was the sole legal tender, Walter’s determination was evident as he carried a briefcase brimming with 20,000 bills, ready to secure the deal. The first purchase sparked a pivotal moment, as the duo then flipped the land to the government for the construction of the esteemed Provincial Legislative Building—a landmark deal that showcased the duo’s flair for persistence and opportunity.
1909-1920
Making Their Mark
1909
Walter H.A Hill and E.A. McCallum expand the company by forming Western Surety Company. Over time, this new venture would become Canada's only federally chartered insurance provider that writes contract surety bonds for the construction industry and commercial surety bonds.
Walter H.A Hill and E.A. McCallum expand the company by forming Western Surety Company. Over time, this new venture would become Canada's only federally chartered insurance provider that writes contract surety bonds for the construction industry and commercial surety bonds.
1914
McCallum Hill & Company bet big on the growth of the province and develop Regina’s first skyscraper, The McCallum Hill Building. This 10-storey office tower, heralded as "one of the most modern buildings of the west," opened its doors to tenants on January 1, 1914.
McCallum Hill & Company bet big on the growth of the province and develop Regina’s first skyscraper, The McCallum Hill Building. This 10-storey office tower, heralded as "one of the most modern buildings of the west," opened its doors to tenants on January 1, 1914.
1939-1947
An Evolving Enterprise
1939
Following the deaths of E.A. McCallum and his brother, E.D. McCallum, Walter Hill and his family take complete control over McCallum Hill & Company and establish The Hill Companies.
Following the deaths of E.A. McCallum and his brother, E.D. McCallum, Walter Hill and his family take complete control over McCallum Hill & Company and establish The Hill Companies.
1947
Fred Hill joins the family business following a decorated and distinguished tour as a pilot with the United States Air Force during World War II.
Fred Hill joins the family business following a decorated and distinguished tour as a pilot with the United States Air Force during World War II.
1960-1969
Regina Residential Expansion
1960-1969
The Hill Companies experience significant growth in Regina's residential real estate market, developing iconic neighbourhoods such as Hillsdale, Normanview, Gryphons Walk, Qu'Appelle Village, and Centennial Gardens.
The Hill Companies experience significant growth in Regina's residential real estate market, developing iconic neighbourhoods such as Hillsdale, Normanview, Gryphons Walk, Qu'Appelle Village, and Centennial Gardens.
1970-1979
Third Generation and Expanding Presence
1977
Paul J. Hill, son of Fred, assumes the role of general manager of The Hill Companies.
Paul J. Hill, son of Fred, assumes the role of general manager of The Hill Companies.
1977
The Hill Companies enter the media industry and establish Harvard Broadcasting following the acquisition of CKCK-TV, a prominent CTV affiliate station in Regina.
The Hill Companies enter the media industry and establish Harvard Broadcasting following the acquisition of CKCK-TV, a prominent CTV affiliate station in Regina.
1978
Fred Hill announces that Paul Hill will succeed him as President, marking the start of the third generation of family ownership within The Hill Companies.
Fred Hill announces that Paul Hill will succeed him as President, marking the start of the third generation of family ownership within The Hill Companies.
1979
Harvard Developments, the real estate division of The Hill Companies, expands its operations into Alberta by constructing two prominent office towers: the Norcen Tower and the Alberta Stock Exchange Tower in Calgary.
Harvard Developments, the real estate division of The Hill Companies, expands its operations into Alberta by constructing two prominent office towers: the Norcen Tower and the Alberta Stock Exchange Tower in Calgary.
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1980s
Embracing Innovation
1981
Harvard Broadcasting diversifies its portfolio by acquiring Regina radio stations CKRM and CFMQ, setting the stage for future growth and innovation.
Harvard Broadcasting diversifies its portfolio by acquiring Regina radio stations CKRM and CFMQ, setting the stage for future growth and innovation.
1982
The original McCallum Hill Building is demolished, paving the way for Harvard Developments to develop the Bank of Montreal building, Hill Centre Towers I and II, and Hamilton Centre/FCC Tower.
The original McCallum Hill Building is demolished, paving the way for Harvard Developments to develop the Bank of Montreal building, Hill Centre Towers I and II, and Hamilton Centre/FCC Tower.
1982:
The Hill Companies enter the energy sector by acquiring Tenneco Oil of Canada Ltd., leading to the formation of the Harvard Energy Partnership (HEP). They further expand by establishing Harvard Investments in Scottsdale, Arizona, a company specializing in creating and developing award-winning residential communities.
The Hill Companies enter the energy sector by acquiring Tenneco Oil of Canada Ltd., leading to the formation of the Harvard Energy Partnership (HEP). They further expand by establishing Harvard Investments in Scottsdale, Arizona, a company specializing in creating and developing award-winning residential communities.
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1990s
Continuing Momentum
1991
Paul Hill, the Regina Economic Development Authority, the private sector, and the City of Regina collaborate to relocate Farm Credit Canada and Crown Life Insurance head offices to Regina. This move creates over 1,100 jobs and boosts the province's GDP by 2%.
Paul Hill, the Regina Economic Development Authority, the private sector, and the City of Regina collaborate to relocate Farm Credit Canada and Crown Life Insurance head offices to Regina. This move creates over 1,100 jobs and boosts the province's GDP by 2%.
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1996
McCallum Hill Insurance merges with Cooks Insurance, forming Cooks McCallum Hill Insurance.
McCallum Hill Insurance merges with Cooks Insurance, forming Cooks McCallum Hill Insurance.
2000-2010
Retail Revolution
2001
Western Surety Company opens its first branch office in Halifax, Nova Scotia, to meet the growing demand in Atlantic Canada. In 2009, the company caps its 100th year in business by opening a second branch office in Toronto, Ontario.
Western Surety Company opens its first branch office in Halifax, Nova Scotia, to meet the growing demand in Atlantic Canada. In 2009, the company caps its 100th year in business by opening a second branch office in Toronto, Ontario.
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2004
Harvard Developments purchases Eau Claire, a prime location in Calgary's downtown core. The iconic Eau Claire Market anchors the neighbourhood and would serve as a vibrant gathering spot for surrounding communities for two decades.
Harvard Developments purchases Eau Claire, a prime location in Calgary's downtown core. The iconic Eau Claire Market anchors the neighbourhood and would serve as a vibrant gathering spot for surrounding communities for two decades.
2008-2010
Harvard Developments breaks ground on Currents of Windermere in Edmonton and Grasslands in Regina, two major commercial properties. These open-air retail shopping centres span nearly 200 acres combined and feature a mix of local and national brands.
Harvard Developments breaks ground on Currents of Windermere in Edmonton and Grasslands in Regina, two major commercial properties. These open-air retail shopping centres span nearly 200 acres combined and feature a mix of local and national brands.
2010
Cooks McCallum Hill Insurance merges with Western Financial to form Harvard Western Insurance.
Cooks McCallum Hill Insurance merges with Western Financial to form Harvard Western Insurance.
2012-2020
Building Toward the Future
2012-2016
Harvard Developments completes the construction of Mosaic Tower at Hill Centre III and Agriculture Place in Downtown Regina. The company also purchases 201 Portage, a 33-storey office tower in Winnipeg.
Harvard Developments completes the construction of Mosaic Tower at Hill Centre III and Agriculture Place in Downtown Regina. The company also purchases 201 Portage, a 33-storey office tower in Winnipeg.
2015
The Hill Companies establish Harvard Integrations in South Dakota, a company specializing in the design and manufacture of pre-fabricated modular enclosures to protect mission-critical electrical equipment for data centers, industrial and utility sectors.
The Hill Companies establish Harvard Integrations in South Dakota, a company specializing in the design and manufacture of pre-fabricated modular enclosures to protect mission-critical electrical equipment for data centers, industrial and utility sectors.
2018
Harvard Western Insurance expands its presence in rural Saskatchewan by acquiring Hoff Insurance. This is followed by the strategic purchases of Tilley’s Insurance Agency and Dalmeny Insurance in 2023.
Harvard Western Insurance expands its presence in rural Saskatchewan by acquiring Hoff Insurance. This is followed by the strategic purchases of Tilley’s Insurance Agency and Dalmeny Insurance in 2023.
2019
Harvard Energy Partnership and Harvard Resources acquired a 14% working interest in the Weyburn-Midale CO2 Project. The world-renowned project has safely stored over 36 million tonnes of CO2 underground since production began, capturing almost 2 million tonnes annually.
Harvard Energy Partnership and Harvard Resources acquired a 14% working interest in the Weyburn-Midale CO2 Project. The world-renowned project has safely stored over 36 million tonnes of CO2 underground since production began, capturing almost 2 million tonnes annually.
2021-Present
Fourth Generation and Further Expansion
2021
Harvard Broadcasting acquires the digital marketing agency Carbon Marketing and rebrands itself as Harvard Media. This transformation allows the company to shift its focus from radio to creating multiplatform content, advertising, and digital marketing solutions across Western Canada and beyond.
Harvard Broadcasting acquires the digital marketing agency Carbon Marketing and rebrands itself as Harvard Media. This transformation allows the company to shift its focus from radio to creating multiplatform content, advertising, and digital marketing solutions across Western Canada and beyond.
2021
Harvard Investments acquires 18,000 acres of undeveloped land in Goodyear, Arizona, with plans to develop Estrella, the largest master-planned community in the state.
Harvard Investments acquires 18,000 acres of undeveloped land in Goodyear, Arizona, with plans to develop Estrella, the largest master-planned community in the state.
2022
The Hill Companies embrace a new chapter with the elevation of Rosanne Hill Blaisdell and Matthew Hill, children of Paul Hill, to leadership roles. Rosanne takes the helm as President and CEO of Harvard Developments Corporation and its Canadian real estate affiliates, while Matthew is named President and CEO of Harvard Diversified Holdings. This marks the fourth generation of the Hill family’s leadership, blending tradition with a forward-looking vision.
The Hill Companies embrace a new chapter with the elevation of Rosanne Hill Blaisdell and Matthew Hill, children of Paul Hill, to leadership roles. Rosanne takes the helm as President and CEO of Harvard Developments Corporation and its Canadian real estate affiliates, while Matthew is named President and CEO of Harvard Diversified Holdings. This marks the fourth generation of the Hill family’s leadership, blending tradition with a forward-looking vision.
2023
The Hill Companies celebrate 120 years of business and are inducted into the Saskatchewan Business Hall of Fame for their contributions to economic development and community well-being within the province.
The Hill Companies celebrate 120 years of business and are inducted into the Saskatchewan Business Hall of Fame for their contributions to economic development and community well-being within the province.
Today
The Hill Companies have firmly established itself as an organization as impressive as it is capable, with successful operations spanning a variety of sectors, including real estate, insurance, media, manufacturing, and oil and gas.
