The Trust was founded in 1974 by a group of friends, patients, colleagues and former students of Dr. Arthur H. Squires, as a way for everyone to honour him for his practice of the art and well as the science of medicine. Dr. Squires was a wonderful man who in his medical practice combined academic excellence and interest in research and teaching with the amazing ability to provide the support and empathy his patients needed.
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In 2010, the Squires Trust became the Squires-Hyland Trust, to recognize and honour the leadership of Dr. Robert H. Hyland in advancing the work of the Trust.

After careful consideration of the mandate and purpose "To promote the Art as well as the Science of Medicine," again in 2010, the Board of the Squires-Hyland Trust re-energized the mission of the Trust through the creation of a One Million Dollar commitment to enhance the existing Chalmers Professorship and create the Squires-Chalmers Professorship in conjunction with the Department of Medicine at the University of Toronto. This endowment created an annual revenue stream used by the Physician-in-Chief of St. Michael's Hospital to support the Department of Medicine for clinical work, research and teaching.

Using money raised through the annual fundraising dinners, donations and bequests, the Squires-Hyland Trust has distributed approximately $2 Million (in today's dollars) in support of various medical programs and initiatives at St. Michael's Hospital.