- Appointed to the Supreme Court of Canada.
- Adamson's novel The Outlander won the Books in Canada First Novel Award in 2008.
Jeremy Adelman (b. 1960)
- Professor and Chair of the History Department at Princeton University.
- Senior Legal Counsel at McDonald’s Restaurants of Canada.
- Frank and his brother Leo opened a record store, "2001 Record and Stereo Centre", at Dovercourt and Bloor in 1971. Their business, now known as "2001 Audio Video", is now one of Ontario's largest electronics retailers, and Frank is President and CEO.
Herbert Stoker Armstrong (1915-1993)
- Earned a BA and MA from the University of Toronto, and a PhD in geology from the University of Chicago. Professor and Dean at McMaster University and the University of Alberta, Armstrong was the first President of the University of Calgary, and later became Dean of Graduate Studies at the University of Guelph. He received an honorary doctorate from the University of Calgary in 1972.
John D. Arnup (b. 1911)
- Notable lawyer. Elected a bencher of the Law Society of Upper Canada in 1952, and served as its Treasurer from 1963 to 1966. He negotiated a new program of legal education in Ontario, and contributed to the creation of accredited university law schools and the institution of the Bar Admission Course. He also conducted negotiations with the Attorney General of Ontario concerning a sponsored legal aid plan for the province. Arnup was appointed a justice of the Ontario Court of Appeal in 1970, and served until his retirement in 1985. Officer of the Order of Canada (1989).
Harry William Arthurs (b. 1935)
- Former Dean of Osgoode Hall Law School and President of York University. Member of the Order of Ontario, and the Order of Canada.
- Vice-President for Academic Affairs at Oakwood University in Huntsville, Alabama. Oakwood University is a private, historically black university owned and operated by the Seventh-day Adventist Church.
- Architect and author of Historic Buildings of Canada. Founding member of The Association for Preservation Technology. Ayer led a campaign in the 1960s to preserve Toronto's Old City Hall.
Allan A. Bailey (1919-1967)
- Professor and Head of the University of Saskatchewan's Department of Medicine. President of the Canadian Neurological Society, and Chairman of the Association of Neurologists.
- Professor and Chief of Oral and Maxillofacial Surgery at Mount Sinai Hospital.
- Physician, academic, and cancer researcher, whose work has helped to improve the understanding of human leukemia and other cancers. As a student, Baker played in Oakwood's orchestra. Recipient of the 125th Anniversary of the Confederation of Canada Medal, and the Queen Elizabeth II Golden Jubilee Medal. Member of the Order of Ontario and Order of Canada.
Our first location. From 1907 to 1910, the "Harbord Annex" (later renamed "Northwestern High School") occupied the top floor of King Edward Public School at Bathurst and College. We moved to our present location--first called "Oakwood High School"--in 1910.
James Hamilton "Jimmy" Ballantyne
- WWII fighter pilot stationed in Malta. Flight Sergeant Ballantyne was a skilled aviator responsible for shooting down five enemy planes during the defence of Malta, and was awarded the Distinguished Flying Medal. Ballantyne was killed in action flying over Evereux France on March 8, 1944, at age 26, and was buried in the Communal Cemetery, St. Andre-De-L'Eure, Eure, France.
Micah Barnes (born 1960)
- Member of "The Nylons". In 2003, he collaborated on the dance track Welcome to My Head, which reached number one on the Billboard club charts.
Laurence (Chip) Barrett
- Played for Toronto Argonauts in the 1960's and 1970's.
Mary Robb Barrow
- A gifted musician, Barrow was the principal horn in the Toronto Symphony from 1939 to 1945.
John Gordon Bates
- Co-founder of MADD Canada. Member of the Order of Canada.
Francis Wright Beare (1902-1986)
- Educator, clergyman and New Testament scholar. First editor of the Oakwood Oracle. Received a Ph.D. from the University of Chicago, and became a professor of New Testament Studies at Trinity College. Ordained an Anglican deacon in 1948. The F.W. Beare Award is offered annually by the Canadian Society of Biblical Studies.
- Director of the Global Effort to Coordinate HIV Vaccine Development for the Bill and Melinda Gates Foundation. Recipient of the McLaughlin Medal of the Royal Society of Canada, the Robert L. Noble Prize from the National Cancer Institute of Canada, the Genetics Society of Canada Award of Excellence, the 2001 Australian Society of Medical Research Medal, the 2007 Medaille du merite from the Institut de Recherche Clinique de Montreal, and the 2008 Gairdner Wightman Award. Member of the Order of Canada (2002). He is a Senior Fellow at Massey College, University of Toronto.
Looking east on St. Clair from Lauder Avenue, 1911. Oakwood Collegiate is at the top right, and in the centre-right are trees next to the west branch of Garrison Creek (called "Springmount Stream") where students would swim and play after school.
- Lawyer. Betty was an Ontario Crown Attorney, and later represented the Government of Jamaica in deregulating their telecommunications infrastructure. He is a member of the Mayor’s Task Force on Economic Development, as well as the Toronto Police Training Committee. Betty is a member of the Law Society of Upper Canada and the Bar of Jamaica and has been honored with the City of Toronto William Hubbard Award, the Planet Africa Leadership Award, and is the recipient of a Queen's Diamond Jubilee Medal.
- Juno Award-winning R&B singer-songwriter. She has collaborated and written for many artists, including Nas, Saukrates, Choclair, Kardinal Offishall, Destiny's Child and Sean Paul, and was chosen by CBC Music as one of "The 25 Greatest Canadian Singers Ever." Black has been dubbed "Canada's Queen of R&B".
- Sport shooter who competed in the Summer Olympics in 1952, 1956, 1960, 1964 and 1972.
Robert J. Bourchier (graduated 1946)
Alexander Brady (1884-1985)
- Director-General of the Canadian Forestry Service.
- Studied at Oxford on a scholarship, then completed his PhD at the University of Toronto, where he went on to become a professor. Brady taught at U of T for nearly 50 years, and was part of a group in the 1930's that pioneered the study of international relations and Canada's place in the world. Brady published numerous articles and several books, including D'Arcy McGee and Democracy in the Dominions.
Looking west on St. Clair from Winona across the east branch of Garrison Creek (called "Humewood Reach"), with Oakwood Collegiate in the distance, 1911.
Lionel G. Brayley
- Studied medicine at the University of Toronto. In 1958, Brayley became the first chief of medical staff at South Peel Hospital (now The Mississauga Hospital).
- Entrepreneur, stand-up comedian and actor best known for being the co-founder (along with Joel Axler) of “Yuk Yuk's”, the largest chain of comedy clubs in Canada. Noted for stating: "When I was in grade 9, in 1965, I joined a group at Oakwood Collegiate called SUPA (Student Union for Peace Action), which guaranteed that an RCMP file would follow for the rest of my life".
Adalgisio Joe Bria
- Principal of St. André Catholic School in Toronto.
Jane Bunnett (b. 1956)
- Soprano saxophonist, flutist, and bandleader known for her Afro-Cuban jazz melodies. Bunnett has won four Juno Awards, and is an Officer of the Order of Canada (2004). In 2006, she was awarded an honorary Doctorate from Queen's University.
Barbara M. Camm (d. 2009)
- School Superintendent with the former Toronto Public School Board.
Torquil Campbell (b. 1972)
- Co-lead singer and songwriter for the Montreal-based indie rock band “Stars”.
- Founding member of the band "Broken Social Scene" and veteran indie rock performer who has been a member of various notable bands including By Divine Right, Blurtonia, Valley of the Giants, Len, and hHead.
- Businesswoman and politician. Caplan served in the Legislative Assembly of Ontario from 1985 to 1997, and was a Member of Parliament from 1997 to 2004. She served as a cabinet minister in the provincial government of David Peterson and the federal government of Jean Chrétien.
- TDSB Principal and author of investment books and articles. Carroll wrote: "My search for a better start took me 40 minutes away by bus to a school called Oakwood Collegiate. This was to be one of the best decisions of my young life".
- Comedian on “The Kids in the Hall”. The comedy troupe rehearsed in Oakwood's auditorium in 1982-83.
- Italian-born classical crossover tenor, music producer and composer.
- Director of feature films, television movies and mini-series. Ciccoritti has received 8 Gemini Awards, 3 Directors Guild of Canada Awards, and a Genie nomination.
E. Ritchie Clark (1912-2007)
- Served as a flying officer with the RCAF during World War II, and commanded an RAF radar station. In 1947 he joined the Industrial Development Bank of Canada (now the Business Development Bank of Canada), retiring 30 years later as Executive Vice-President and Chief General Manager.
James Charles MacLeod Clarke
- Clarke earned a Licentiate in Theology from Trinity College in 1944. For most of his career he served as an Anglican minister in the Canadian arctic, living in Fort Chimo, Aklavik, Ungava, Moosonee, and Iqaluit. In 1979, Clarke was appointed Suffragan Bishop of the Arctic, and in 1986, Bishop Ordinary to the Canadian Armed Forces. Clarke earned a Doctor of Divinity from Trinity College in 1981.
- Professor and author. While at Oakwood in 1983, Clarke co-founded the first Afro-Canadian club in a Toronto high school. In both 1984 and 1985, she was Athlete of the Year. Clarke earned a Master of Law degree from Yale University, and has written extensively on issues of social justice.
Gerald Hall Clawson (1917 - 2001)
- Competed in the 1936 Berlin Olympics as a swimmer. The following year he was Oakwood's Valedictorian. Served as a Lieutenant in the Irish Regiment of Canada during WWII and was awarded the Military Cross for Bravery.
Carl Cole (d. 1994)
- Co-founder of Coles Bookstore, once the largest bookstore chain in Canada.
Clarence Cecil Cook (1894-1982)
- Professor of Physics and Director of Studies at Royal Roads Military College (now Royal Roads University). The Clarence C. Cook Memorial Scholarship is awarded annually by the University of Victoria.
William James Copeman (1923-2004)
- Family doctor in Sundridge, Ontario, where he also served as councillor and reeve.
- Musician with the bands "The Stars" and "Broken Social Scene".
Dianne Esther Cunningham (b. 1939)
- Progressive Conservative member of the Legislative Assembly of Ontario from 1988 to 2003, and cabinet minister in the governments of Mike Harris and Ernie Eves.
- Writer for the Toronto Telegram and Toronto Sun. Currell wrote: "I enrolled at Oakwood Collegiate where I was to endure a chequered career".
Wesley "Wes" Cutler (b. 1911)
- Star football player in the Canadian Football League for six seasons for the Toronto Argonauts. He was inducted into the Canadian Football Hall of Fame in 1968 and into Canada's Sports Hall of Fame in 1975.
- Dadson received a Ph.D. in geology from the University of Toronto in 1938, then began working in northern Canada where he unraveled the complex geology and outlined minable zones on what was to become the biggest and richest gold deposit in the Northwest Territories. A quiet and generous man, he was frequently described as "one of the unsung heroes of mineral exploration in Canada." Dadson's name was added to the Canadian Mining Hall of Fame, and the mineral Dadsonite is named in his honour.
Bryan P. Davies
- Chair of the Canada Deposit Insurance Corporation; Chief Executive Officer and Superintendent of the Financial Services Commission of Ontario; Senior Vice-President at Royal Bank Financial Group; Ontario Deputy Treasurer and Deputy Minister of Economics; Vice-President of Business Affairs and Chief Administrative Officer at the University of Toronto.
Leonard Spencer Davies
- Chief of Orthopaedics at Scarborough General Hospital from 1965 to 1985.
Richard E. G. Davis (b. 1894)
- Executive Director of the Canadian Welfare Council. Davis contributed to the development of social welfare programs across Canada. Awarded an honourary Doctor of Laws from the University of British Columbia (1955); Officer of the Order of Canada (1973).
Vincent Del Buono
- Lawyer. His achievements include: student council president at Oakwood Collegiate; first president of the International Society for the Reform of Criminal Law; senior counsel to the Law Reform Commission of Canada; senior adviser to the United Nations Office on Drugs and Crime, Vienna; attached to UN peacekeeping operations in Bosnia and Herzegovina; served as deputy secretary-general of Amnesty International, London; headed the British Council's Access to Justice program in Nigeria.
Southeast corner of Oakwood Collegiate, 1921
Arthur P. Dempster
- Professor Emeritus in the Harvard University Department of Statistics.
- Senior scientist at Ottawa Hospital Research Institute where he investigates cancer therapies.
- Professional athlete who played football with the Toronto Argonauts from 1922 to 1924. In 1924 he joined the Montreal Maroons of the NHL, and on December 1, 1924, he earned the first goal ever scored against the Boston Bruins.
- Key figure in Canada's diplomatic corps. While stationed at the Canadian Embassy in Tehran, Iran, during the late 1970’s, Dollimore played a key role in the "Canadian Caper" which rescued six American diplomats who had evaded capture during the seizure of the United States Embassy. Member of the Order of Canada.
- President of CAPUT (Oakwood's student council) in 1949. Member of Parliament from 1979 to 1993. Best known for his crusades against the metric system and support of capital punishment.
William J. Dow
- In 1996, Dow was named President and Chief Executive Officer of Daily Racing Form, the most widely published source of race horse statistics in North America.
Linda Silver Dranoff
- Lawyer and author. Founding Chair of the Ontario Bar Association’s Feminist Legal Analysis Section. Recipient of the Law Society Medal, the Governor General’s Award, and the Ontario Bar Association’s Distinguished Service Award. Member of the Order of Canada (2012).
- TDSB vice-principal at Malvern Collegiate. Noted for receiving his PhD from the University of Toronto at age 76.
Tyrone "T-RexXx" Edwards
- Host of E! Movie Night, one of the creators of 1 LOVE T.O., and former host on MuchMusic's RapCity.
Norman J. Endicott
- Teacher, author and Rhodes Scholar.
- Actress who starred as Anne Shirley in the film Anne of Green Gables: A New Beginning (2008).
Vivien Endicott-Douglas (b. 1990)
- Music producer and keyboardist, best known for his work with Lou Reed, Alice Cooper, Kiss, Pink Floyd, Peter Gabriel, and Phish. Ezrin is a Juno Award recipient and was inducted into the Canadian Music Hall of Fame in April 2004.
Anna Faull (graduated 1922)
- Harvard PhD, prolific author, and well-regarded Professor of Botany at Cambridge University.
- Novelist, playwright, actress and poet. Fielden is a founding member of both the Writers' Union of Canada and the Playwrights Guild of Canada.
G. Vernon Fisk
- Graduated from Dentistry at the University of Toronto, specializing in orthodontics. Fisk authored numerous publications about dentistry, and served as President of the Canadian Dental Association from 1949-50.
- Emmy (2000) and Cannes (2004) Award-winning conductor and violinist.
Received a Ph.D. from Dalhousie University, and then taught history for 35 years at the University of New Brunswick. A former editor of Acadiensis, the journal of Atlantic regional history, Frank has published numerous studies in Canadian history.
- Journalist, writer and academic who served as Master of Massey College at the University of Toronto. Member of the Order of Canada (2001).
- Poet and playwright. Member of the Order of Canada (2001).
- Chief Administrative Officer and Chief Financial Officer at the Royal Bank of Canada.
- Engineer at Avro Canada, then worked in Flight Controls at NASA on the Apollo program.
- Guitarist in “Platinum Blonde”.
Elizabeth H. Gillespie
- Gillespie entered nursing during the Depression, and served overseas as a nurse during the war. She spent two decades with the World Health Organization in India, Egypt, Thailand, Sri Lanka and Burma, and then worked in Africa as a public health nurse in Malawi and Kenya. She later earned a master’s degree from Columbia University. Gillespie bequest $1 million to the Faculty of Nursing at the University of Windsor, and the Gillespie Memorial Scholarship is named in her honour.
By 1923, a third floor had been added.
John Judah Glass (1895–1973)
- Glass served in World War I, and then became a lawyer. He was a Toronto alderman from 1931 to 1934, and then represented the largely immigrant ward of St. Andrew in the Legislative Assembly of Ontario from 1934 to 1943. As chairman of the Toronto's parks commission in 1932, Glass is noted for his effort to eliminate "gentiles only" signs from Toronto Island. As MPP, Glass introduced provincial legislation against racial slander.
William Gary Glover (1931-2015)
- At age 40, Glover became the youngest President of Control Data Canada, one the earliest and most successful computer companies in Canada.
- Received a B.Phil and D.Phil. from Oxford University, and is currently Professor Emeritus at the University of Toronto. A philosopher, writer and political activist, Goldstick is a long-time member of the Central Committee of the Communist Party of Canada and has been a frequent candidate at the federal and provincial level.
- Radio personality. Green hosted the first music show on CITY-TV, and co-hosted After Four, a national children’s show on CBC-TV. Green hosted a weekly jazz show on CFNY-FM, and syndicated his Out of The Blue show nationwide. While working for JAZZ FM91 in 2006, Green won the National Jazz Broadcaster of the year award.
Roy Greenaway (1891-1972)
- Full-time reporter/photographer for the Toronto Daily Star. Greenaway was a prolific painter; his works are among the Government of Ontario Art Collection and the City of Toronto Art Collection.
Arnold Kingsley Graham
- Ambassador to Sweden in 1959.
Harry L. Guy (1903-1959)
- Studied mathematics at the University of Toronto, then joined the actuarial department at Mutual Life of Canada in 1927. In 1955, Guy was elected to the company's Board of Directors, and in 1958 he became President. Guy was named a Commander of the Order of the British Empire for his leadership with the National War Finance Committee, and was President of the Actuarial Society of America.
- Halpenny became Associate Director of the University of Toronto Press in 1941. She later served as Dean of the University's Faculty of Library Science, and was editor of the Dictionary of Canadian Biography. Officer and Companion of the Order of Canada.
James Milton Ham
- Pioneer in the teaching and promotion of research in the field of automatic control. Ham served as Dean of the Faculty of Applied Science and Engineering in 1966 and Dean of Graduate Studies in 1976 at the University of Toronto. He was awarded an honorary doctoral degrees from 13 universities in Canada and Korea. Officer of the Order of Canada (1980), and Order of Ontario (1989).
- Rugby sevens gold medalist at the 2015 Pan Am Games. Member of Canada's Olympic rugby team.
Sharon Trostin Hampson
- Member of the children's musical trio Sharon, Lois & Bram.
- Harrison dropped out of Oakwood before graduating to serve as a navigator with a Royal Canadian Air Force bomber squadron in England during WWII. He returned to Canada and studied political science and economics at the University of Toronto. Harrison joined the Toronto Star in 1949 and worked as a reporter, assistant city editor, London bureau chief, and in 1969, executive editor. In 1976, Harrison became editor of the Montreal Gazette.
- Played for the Toronto Maple Leafs, where he won the Stanley Cup in 1951. Hassard also played with the Chicago Black Hawks. The Brooklyn Dodgers baseball team offered him $100 a month to play for their farm team, but Hassard turned down the offer because he could earn more as a hockey player.
Alan Milliken Heisey (d. 2014)
- Attended Harvard University. Served two terms as a North York Alderman, earned a commission in the Toronto Scottish Regiment, had a private pilot’s licence, and was an occasional business commentator on Global TV. A writer, pamphleteer and blogger, he contributed to Time magazine, the New York Times, and many other publications, and was the author of the book The Great Canadian Stampede.
- Head of the Biochemistry Department at Delhousie University from 1964-69.
Gerald K. Helleiner
- President of CAPUT (Oakwood's student council) in 1954. Professor Emeritus in the Department of Economics, University of Toronto. From 1991 to 1999, he served as research director of the Group of 24 (the developing countries' caucus at the IMF and World Bank). Officer of the Order of Canada.
- Canada’s foremost expert on hip hop culture. Author of Far From Over, the first biography of musician Drake. Higgins examines the interconnection of technology, race, hip hop, and hipster culture . Recipient of a Canadian National Magazine Award in 2000.
Eastbound streetcar in front of Oakwood Collegiate, 1928
- Played 12 seasons in the National Hockey League as a defenceman for the Ottawa Senators and Boston Bruins. Hitchman was the first Captain of the Boston Bruins, leading them to their first Stanley Cup victory in his first year. He later became a sergeant in the Royal Canadian Mounted Police.
Bruce I. Hochman (d. 2001)
- Hockman moved to California and was a member of UCLA Law School's inaugural class in 1952. He founded a Beverly Hills lawfirm and gained a reputation as "the dean of tax litigators in Los Angeles". Hockmand was known for his philanthropy and civic leadership, former US Vice President Al Gore describing him as "a man of flawless integrity". UCLA Law School's "Bruce I. Hochman Award" is presented annually.
Stanton Bardsley Hogg
- Ontario Superior Court Judge.
Faithe Holder (graduated 1994)
- Partner at Gowlings Law Firm and head of its Real Estate, Environmental and Urban Development Department in Toronto.
- Author and Rhodes Scholar. Hornyansky taught English Language and Literature at Carleton University. Recipient of Newdigate prize for poetry in 1951, and Officer of the Order of Canada (2001).
- Sports reporter for the Toronto Telegram and Toronto Sun. Iaboni covered all major teams and leagues, but primarily the Toronto Maple Leafs. Iaboni covered 10 Olympics, from 1976 to 2010.
- Professor of Social Work, and author of Reading Foucault for Social Work.
- Musical supervisor for The Lion King.
Mary V. Jackson
- In 1930, after graduating medical school, Jackson became the first female resident at the Toronto Psychiatric Hospital (now the Clarke Institute), and later went on to become Assistant Director of the Clark Institute. Jackson was also the first woman to hold senior academic and administrative posts at the University of Toronto's Department of Psychiatry. No female psychiatrist in Canada before Jackson reached such prestigious academic, administrative and professional posts.
Marion Jane (Lawson) Johnston (1910-2006)
- Johnson obtained a Ph.D. in biochemistry from the University of Toronto, then moved to Halifax with her husband, where they were instrumental in the development of Cod Liver Oil. Johnson later worked as a supply teacher in Toronto.
- Sportscaster for ESPN/ABC since 1990, where he covers college football and NBA games.
- Toronto Raptors' radio play-by-play announcer on Fan 590. Former school principal in York Region.
Joseph Charles Kane (1928-2005)
- At age 49, Kane was one of the youngest judges ever appointed in Ontario, and served on the bench until 1997 as a Superior Court Judge. Kane's passion was hockey. He coached house league, was a director with Hockey Canada, and worked as an arbitrator with the NHL.
- Former Toronto District School Board Trustee for Ward 5.
- Chief Geologist with the National Energy Board. Kerr authored eight books, and in 1998 received an honourary doctorate from the University of Calgary. He was inducted into the Canadian Petroleum Hall of Fame. Brother of Donald Kerr.
Donald Peter Kerr (1920-2008)
- Chair of the University of Toronto's Department of Geography (1968-72), and Associate Dean of the School of Graduate Studies (1978). Kerr authored several books and papers on Canadian geography, climate and urban studies, and co-edited the Historical Atlas of Canada (Volume III, 1990). President of the Canadian Association of Geographers (1960) and member of the Royal Canadian Geographical Society (gold medal, 1984).
- Conductor of the Vancouver Pops Symphony, and of the Royal Conservatory Orchestra. Music Director at the Centre in Vancouver for the Performing Arts.
- Kling taught urban studies and geography at Ryerson, where he developed a course on vacationing and retiring in Florida. It became one Ryerson's most popular evening courses, and led to Kling publishing two bestselling books: How to Retire and Invest Successfully in Florida (1982), and It's Never Too Early: A Guide to Planning and Enjoying Your Retirement Lifestyle (1985). During the 1950s, Kling studied and did research in Havana at the same university attended by Fidel Castro. This led to Kling's lifelong attraction to the Caribbean and his love of Cuban cigars.
- Pharmacist, businessman, and philanthropist. Best known for creating the Canadian pharmacy retailer, Shoppers Drug Mart. Member of the Order of Ontario (1992) and Officer of the Order of Canada (1995).
R. Brian Land
- Dean of University of Toronto's Faculty of Library Science and Director of the Legislative Library of Ontario.
James Laxer (b. 1941)
- Political economist, professor and author. At age 20 he ran for the leadership of the federal NDP, and shocked the convention by winning one-third of the vote against party stalwart David Lewis. The son of Robert Laxer, James wrote: "I started grade nine at Oakwood Collegiate. Oakwood was an unusual school, especially if you were the son of a full-time Communist organizer".
Nathan Nauson Levinne (b. 1917)
- Chief of the Family Practice Unit at Mount Sinai Hospital. Chief of staff and chairman of the Medical Advisory Committee.
- Provincial secretary of the NDP during the 1980s. Brother of Stephen Lewis.
- Leader of the Ontario New Democratic Party for most of the 1970s. Canada's United Nations ambassador in 1980s. United Nations' special envoy for HIV/AIDS in Africa in 2000s. Member of Order of Canada.
Peter Li Preti
- Li Preti obtained a doctorate in clinical psychology, and practised as a psychometrist. He served as a North York City Councillor from 1985 to 1997, and a Toronto City Councillor from 1998 to 2006.
Steven N. Liss
- Professor of Environmental Studies and Chemical Engineering at Queen’s University, and Vice-Principal of Research. Vice-Chair of the Ontario Council on University Research, and Chair of TRIUMF, Canada’s national laboratory for particle and nuclear physics. Awarded the Queen Elizabeth II Diamond Jubilee Medal in 2012.
John B. Macdonald
- President of the University of British Columbia from 1962 to 1967. Member of the Order of Canada.
- Bass player for "The Diodes", one of the most successful punk bands in history. Their hit single Tired Of Waking Up Tired rocketed onto North American radio stations. The Diodes opened Toronto's first punk club--Crash'n'Burn--in 1977.
- Former teacher at University of Toronto Schools, and well known Toronto centenarian (over 100 years of age).
- Former assistant coach of the Toronto Raptors, current head coach of Raptors 905.
Harry Mannis (1920-2003)
- Veteran CBC broadcaster. Mannis was hired in 1946 as a radio announcer in Halifax, then moved to Toronto two years later. On radio, Mannis read the nightly news on the Dominion Network, CBC's second English-language network, and in 1949, began reading Nightly News Bulletin on the Trans-Canada Network, CBC's primary network (now known as CBC Radio One). On television, Mannis narrated The Lively Arts from 1961-64, and 20/20, a documentary series which aired from 1962-67. In 1960, his voice was recorded and used on the CBC/National Research Council's official time radio station, where Mannis' voice was heard round-the-clock stating: "NRC Eastern Standard Time... eleven hours, fifty-six minutes, and ten seconds... BEEP"!
- Founded Jerome Markson Architects in 1955. Recipient of the Canadian Housing Design Council Award, the Massey Medal, the Ontario Association of Architects Award, and the Canadian Architect Award.
- While a student at Oakwood, Marsh was consequenced for inappropriate behaviour by having to copy out pages of the encyclopedia in the library. After graduating, he became Editor-in-Chief of the Canadian Encyclopedia. A Member of the Order of Canada, and recipient of the Centenary Medal of the Royal Society of Canada (1986), March wrote:
This military tradition was also a powerful influence at my school, Oakwood Collegiate, where the principal, the vice-principal and the guidance teachers were all ex-Army officers. I remember the guidance teacher best, since like some Dr. Strangelove he would peer out suspiciously over his wooden leg, which he rested on a stool underneath his desk, and demand why it was that I was constantly being thrown out of classrooms. “You obviously have a brain,” he said, “so I won’t have you thrown out of the school.” I liked the idea that someone thought I had a brain. I stared at the sole of his boot and tried to explain my sleepless nights. At least, being a military man, he understood that every young boy’s problem was young girls, but his only remedy seemed to be a stint in the cadets.
G. Arthur Martin
- Criminal defence lawyer. Officer (1991) and Companion (1997) to the Order of Canada, and recipient of an honorary Doctor of Laws degree from Queen's University.
Peter Brown Mason
- Obtained a B.Sc. from the University of Toronto, then joined the Canadian Army in 1943. Mason began working on tire compounds for B.F. Goodrich Canada in 1947, and was named President and Chief Executive Officer in 1969.
New Gym, 1933
Portables on the west side of the school, 1933
Malcolm Wallace McCutcheon (1906-1969)
- Lawyer, actuary and politician. Founder of Argus Corporation. McCutcheon was appointed to the Canadian Senate and sat in the caucus of the Progressive Conservative Party. He served as Minister without Portfolio, and Minister of Trade and Commerce.
George E. McGill
- Flight Lieutenant and navigator during WWII, McGill was forced to bail out and was captured by the Nazi's. Imprisoned and sent to Stalag Luft III, in Zagen, Poland, McGill was one of 76 British, Commonwealth and Allied prisoners of war who escaped via a 101-metre tunnel on the night of March 24-25, 1944. All but three were recaptured. The Gestapo shot 50 escapees, including McGill. A book was written, The Great Escape, which was made into a movie starring Steve McQueen.
Mary di Michele
- Poet and author. Professor of English at Concordia University in Montreal, where she teaches in the creative writing program.
Helen Millichamp (graduated 1925)
- Attended Brown School and then Oakwood where she won many awards. Studied at St Hilda’s College, Oxford, earning a BA in Economics and Political Science with courses in Latin, Greek and French; and at Newnham College, Cambridge, earning an MA in Modern History. Millichamp then taught at a number of schools in England, and served as Headmistress at The Bishop Strachan School in Toronto from 1948 to 1952. Millichamp returned to England where she became Headmistress at Lawnside School in Malvern, England.
Boonaa Mohammed (b. 1987)
- Spoken-word poet and writer of Oromo descent.
- Former Dean of the Faculty of Music at the University of Toronto, and Chair of the Graduate Department of Music.
- Graduated Oakwood in 2002. As a singer-songwriter, Mover's genres include folk, jazz, and children's music. In 2013, her solo album The Stella and Sam won the Juno Award for "Children's Album of the Year".
- Obtained a Ph.D. in Physics at the University of Waterloo in 1970. Muc became Canada's first professional specializing in the occupational and environmental health and safety issues associated with non-ionizing radiation. He served as a consultant to the World Health Organization's International EMF and INTERSUN Projects from 1998-99. Muc founded the company Radiation Health and Safety Consulting in 1993, and continues to work there as a consulting physicist.
- Assistant Deputy Minister, Risk Management and Financial Oversight with the Government of Ontario. Mudrinic was Ontario's Secretariat to the 2015 Pan Am Games.
James F. Murray (1920-2003)
- Graduated University of Toronto medical school in 1943 and served as Captain in the Royal Canadian Army Medical Corps. He was head of plastic surgery and later Surgeon-in-Chief at Toronto East General Hospital, and a pioneer of modern hand surgery in Canada. Murray served as President of the Canadian Society of Plastic Surgeons, and was team doctor for the Toronto Maple Leafs from 1948 to 1964. Known as "Doc", he claimed to have led the Leafs to five Stanley Cup wins. Murray was the head doctor for Team Canada's 1972 Canada-USSR Hockey Series.
Robert Mustard Sr.
- Surgeon-In-Chief at Toronto General Hospital from 1972-78.
Winifred Ellen Needler (b. 1904)
- University of Toronto special lecturer in the Department of Fine Art; keeper of the Near Eastern Collections of the Royal Ontario Museum of Archaeology. Her work with The Brooklyn Museum has been acknowledged as an outstanding achievement that makes Brooklyn’s pre-dynastic and archaic objects readily accessible. Named Curator Emeritus of the Egyptian Department for Life in recognition for her lifelong scholarly contributions to Egyptology at the Royal Ontario Museum. Bishop's University in Lennoxville, Québec awarded her the degree, Doctor of Civil Law, honoris causa.
Jean Newman (d. 1971)
- Newman served as Toronto's Controller (budget chief), and was the first woman to run for Mayor of Toronto.
- While in grade 9 at Oakwood in 1923, Niblock won the Miss Toronto competition. That same year, she was invited to compete in the National Beauty Contest at Madison Square Garden, against "88 Beauties from 88 Cities". Movie star Rudolf Valentino personally selected the winner and awarded the trophy--to Norma Niblock.
Tobias Novogrodsky (graduated 1992)
- Attended Harvard University's John F. Kennedy School of Government. Novogrodsky is Senior Corporate Management & Policy Consultant for the City of Toronto, and was Toronto's senior advisor for the 2015 Pan Am Games. Novogrodsy wrote:
When I attended OCI from 1988-1992, sport and culture were the heart and soul of the school and the platform through which so many students found their voice; learned the value and values of teamwork, dedication, and creativity; and gained the confidence to "perform" and push the limits of personal and group achievement.
- Producer of CBC Radio's Metro Morning.
- Paull won a scholarship from Oakwood to study at the Ontario College of Art. She became a noted book-cover artist at Toronto’s Collins Publishing, and was Managing Editor at the time of her retirement in 1989. Paull donated a significant portion of land to the Bruce Trail, and the Margaret Paull Loop on the Bruce Trail is named in her honour.
Al & Belle Perly
- Founded “Perly's Maps” in 1949.
- Journalist, broadcaster, composer and writer based in Vancouver. His CBC series The Wire won a Peabody Award.
Wilfred Murray Posluns
- Co-founded Dylex Ltd. in 1966, a $2-billion fashion consortium that included Fairweather, Tip Top, Big Steel and Suzy Shier. Posluns is credited with raising $100-million for charity over his lifetime.
- Football player with the Toronto Argonauts in 1922.
- Largely responsible for running the Children's Television Department for the Canadian Broadcasting Corporation, out of the Jarvis Street studios during the 1950s and '60s.
- Stage magician and scientific skeptic best known for his challenges to paranormal claims and pseudoscience. While a student at Oakwood, Randi wrote on an exam "this is a premise I cannot support", then walked out.
Paul Hartley Raney
- Second Lieutenant fighter pilot with the Royal Flying Corps, 66th Squadron. Shot down and killed in WWI.
- Oakwood Valedictorian in 1950, Rasky was a gifted writer with a droll and risqué sense of humour, who wrote for the Vancouver Sun, Globe and Mail, Windsor Star, Toronto Star and New York Herald Tribune. During an interview with Walt Disney, Rasky told Disney about winning a gold medal while a student at Oakwood: "I entered the school oratory contest, and my speech was all about you and Mickey Mouse". Member of the Order of Canada.
New Auditorium, 1960
Harry Rasky (1928 - 2007)
- Documentary producer. Rasky's film Hall of Kings won an Emmy Award in 1966. Member of the Order of Canada (2002).
Escott M. Reid (b. 1905)
- Rhodes Scholar, author, international public servant and academic administrator. As a Canadian diplomat he helped shape the United Nations and NATO. Named a Companion of the Order of Canada, and awarded the Pearson Medal of Peace. At Oakwood, Reid wrote a school essay entitled "Victory Bonds: Why Canadians Should Buy Them" (1918); "The Memorial Service", for the Oakwood Oracle (Spring 1921); and "The Future of Canada", for an oratorical contest (1921).
- Film producer and director. Officer of the Order of Canada.
Robert Dick Richmond (b. 1919)
- Richmond became an aeronautical engineering, then worked in the Mechanical Engineering Division of the National Research Council during WWII. In 1970, he became President of McDonnell Douglas Canada, and in 1974, President and COO of Spar Aerospace. Richmond is credited with establishing the Challenger business jet program as an international competitor, and developing the Space Shuttle's "Canadarm" program at NASA. He is a member of Canada's Aviation Hall of Fame.
- Appointed to the Supreme Court of Ontario in 1976, and to the Court of Appeal for Ontario in 1981.
John Roberts (1933-2007)
- President of CAPUT (Oakwood's student council) in 1951. Oxford PhD elected (and defeated) three times to Canada's House of Commons. Roberts served as Minister of Employment and Immigration, Minister of the Environment, Secretary of State of Canada, and Minister of State for Science and Technology.
Charles Gordon Roland (b. 1933)
- Author, editor, and professor of the history of medicine. Roland was President of the American Medical Writer's Association, he received an honorary doctorate from the University of Manitoba, and was awarded the prestigious John McGovern Medal from Oxford University.
- Cast member on Saturday Night Live during the 1981–82 season.
- Founded the Andrea Rosen Gallery in 1990, one of the most successful contemporary art galleries in New York City.
- Chairman and C.E.O. of Harry Rosen menswear.
Arthur Herbert Keith Russell (1893-1960)
- Russell's accomplishments include serving as an Air Commodore in the Royal Canadian Air Force's technical training program during World War II; senior partner in the law firm of Lester, Russell and Fraser; reeve of Forest Hill village; charter member and past president of the Toronto Flying Club; first vice-president of Empire Life Insurance Company; and former president of the American Radio Relay League.
Mildred "Millie" Ryerson
- Humanitarian, artist, activist and occupational therapist. She married Stanley Ryerson, who from 1935-69 was a member of the Central Committee of the Communist Party of Canada. In 1987, she was awarded the Order of Canada for her role as a pioneer in community engagement, and for providing occupational therapy to marginalized and indigenous communities.
- Author, curator and journalist. Founding Curator of Literary Programming at Luminato.
- Superintendent of Schools with the York Region District School Board.
- Regional President of the Royal Bank of Canada, Ontario North and East.
Robin V. Sears
- Sears began his career as a reporter at City-TV. He then served with a variety of political organizations, including the federal NDP, where he was national director; the Socialist International, where he was assistant general secretary; and the Ontario NDP, where he was Premier Bob Rae's Chief of Staff. Sears is past President of the Empire Club of Canada, and a leader in public relations.
- Member of indie pop band "Stars".
J. Louis Shannon (d. 1954)
- Toronto politician who served many years on Toronto City Council and the Toronto Board of Control.
- During his residence in Saskatchewan, Shapiro was active in politics at the local and provincial level with the Cooperative Commonwealth Federation (CCF) and New Democratic Party (NDP). Member of the Order of Canada (2003).
Myron J. Shapiro (b. 1921)
- One of the first Jewish students admitted to the University of Toronto's medical school, where he studied under Sir Frederick Banting. A captain in the Royal Canadian Army Medical Corps during World War II, Shapiro settled in New Jersey where he became a renowned ear, nose, and throat specialist, authoring more than 100 studies on tumors of the head and neck and pioneering multiple surgical procedures.
- Founder and lead guitarist of indie rock band “Metric”. Also founder of the band “Broken Social Scene”. Won the Juno Award for Producer of the Year in 2013.
- Vice-president of Exhibits and Marketing at the Royal Ontario Museum; Director of Student Recruitment at the University of Toronto.
Andrew Alexander Simone
- Studied medicine at Harvard and became a dermatologist. In the 1980s, he and his wife founded Canadian Food for Children, a volunteer organization which collects funds and food for starving children around the world. The Simone's met with Mother Teresa who encouraged them in their work. Member of the Order of Canada (2000).
- Played on Oakwood's 1923-24 OHA-Junior hockey team. Went on to play for the Toronto Canoe Club, Toronto Falcons, Toronto Maple Leafs, Ottawa Senators, Boston Cubs, and Chicago Shamrocks.
- Owner of Toronto's oldest restaurant, The Senator, and son of Sam the Record Man.
Warren Bertram Snyder
- Snyder competed for Canada in rowing in the 1924 Summer Olympics, winning a silver medal as a crew member in the eights event. He went on to become a medical doctor.
James Dean Somerville
- WWII flying ace. Awarded Distinguished Service Order in 1945.
- Deputy Mayor & Regional Councillor for the Town of Richmond Hill.
- Graduated in 1949. Veteran and pioneer of the Canadian broadcast industry.
Christopher M. Speyer
- Ontario Superior Court Justice.
- Member of the Canadian House of Commons. Despite his slight frame and short stature, he excelled at basketball and hockey at Oakwood. He also edited the school magazine and was valedictorian. Member of the Order of Ontario (2011).
- Staroba placed 7th in the dance competition at the 1960 World Figure Skating Championships in Vancouver.
Boris C. Swerling
- Received a BA from the University of Toronto and a PhD from Harvard in 1948. Swerling was a respected author who taught economics at Stanford, Georgetown, Brown and Harvard; and served with a number of US governmental agencies including the Council of Economic Advisers, the State Department, and the Federal Reserve.
Richard Marcus Tait
- Canadian Ambassador to the European Union, 1978-82.
Betty Edwards Tancock (1911-2009)
- An outstanding swimmer, Tancock set Canadian records in the 1,000 yard and 1 mile event, and competed in the 1932 Olympics. At the time of her death at the age of 98, she was Canada's oldest living Olympian.
Andrew Ernest Joseph "Andy" Thompson (b. 1924)
- Leader of the Ontario Liberal Party and later served as a Senator.
Edward Blake Thompson (d. 1943)
- Grey Cup champion halfback in the Ontario Rugby Football Union. Flight Lieutenant Edward Blake Thompson was reported "missing in action at sea" on April 22, 1943.
- Tulloch came to Canada from Jamaica at age 9. In 2003, he was appointed as a judge to the Ontario Superior Court of Justice, and in 2012, he became the first black judge named to the Ontario Court of Appeal.
Richard E. Tustian
- Oakwood Valedictorian in 1949, Tustian became an architect and planner. Between 1969 and 1990, Tustian was Planning Director for Montgomery County, Maryland, where he oversaw the development of one of the most comprehensive and effective urban growth management systems in the United States. As an educator, Tustian lectured on planning at Johns Hopkins and the University of Maryland, and was Adjunct Professor of City and Regional Planning at the University of Pennsylvania.
- Founder of the advertising agency Northwords/Urban & Co, and associate professor at OCAD.
- Radio and TV journalist, and Member of the Canadian House of Commons.
- Chief of Oral and Maxillofacial Surgery for the Niagara Health System.
Andrus J. Voitk
William Marvin Ward (1917-2001)
- Former Surgeon-in-Chief at The Scarborough Hospital.
- After graduating Oakwood, Ward attended Harvard and Berkeley, then moved to Winnipeg in 1942 to work as a chemist for the Province of Manitoba. He retired as the Director of Environmental Management in 1980, and is credited with many innovations in environmental protection on the federal and provincial levels. An environmental laboratory operated by the Manitoba government was named in his honour.
- Prolific and outspoken Canadian broadcaster, television and radio interviewer and host, author, commentator, and television writer, producer, and director for five decades. Officer (1981) and Companion (2002) of the Order of Canada.
Neil Archibald Watters
- Surgeon-in-Chief at Wellesley Hospital; Professor of Surgery; head of the Royal College Committee in General Surgery; Chief Examiner in Surgery for the Royal College; Chairman of Surgery of the Toronto Academy of Medicine: Governor of the American College of Surgeons: member of the Senate of the University of Toronto.
Al Waxman (d. Jan. 18, 2001)
- Actor and director of over 1000 productions on radio, television, film, and stage. Best known for his starring roles in the television series King of Kensington (CBC) and Cagney & Lacey (CBS). Member of the Order of Ontario (1997) and the Order of Canada (1998).
- Professor of Law at the University of Toronto. Weinrib's major book, The Idea of Private Law, was published by Harvard University Press.
York Wilson (1907-1984)
- Artist known for his murals at Toronto's O'Keefe Centre, the Salvation Army Headquarters, Imperial Oil Building, Bell Telephone Building, and Central Hospital. He was a member of the Royal Canadian Academy of Arts. Wilson attended Oakwood, and was a successful student who won prizes in debating. However, because of his practical joking, the principal advised Wilson to find another school. He transferred to Central Tech.
Ronald Frederick Yeo (1923-1999)
- Woodside obtained a PhD from Harvard, and is a Professor of Chinese and Southeast Asian History at the University of British Columbia. He has written extensively about the history and politics of Southeast Asia. Fellow of the Royal Society of Canada.
- President of the Canadian Library Association, and Chief Librarian for the City of Regina.
- Sportswriter for the Toronto Sun.
Former students who have been members of various Canadian National Basketball Teams:
- Julian Clarke - Santa Clara Broncos
- Norman Clarke
- Paula Edwards-Kovinsky - University of Prince Edward Island basketball star
- Greg Francis
- Kevin Jobity
- O’Neill Kamaka
- Hamilton Nguyen - Competitive amateur archer
- Dean Walker
Never attended our fine school...
Edwin Alonzo Boyd
- Bank robber and leader of the infamous “Boyd Gang”. Two members of his gang were hanged in the Don Jail, while Boyd received eight life sentences--but was paroled in 1962. He is noted for lying on his 1939 army application, claiming to have completed grade 10 at Oakwood Collegiate. Boyd never attended our fine school.