Charlie Sims ’80
2026
Established by the Association Council to recognize a UCC volunteer who has gone “above and beyond,” this award honours those who have shown an outstanding commitment to service to the College over a number of years.
This year’s recipient, Charlie Sims, is president, chief executive officer and director of Cumberland Partners Limited and its subsidiary Cumberland Private Wealth Management Inc. and director of its affiliate, Cumberland Investment Counsel. He’s responsible for Cumberland’s overall business operations and strategic directions. He has 37 years of experience in the investment industry in Canada, the United States, Europe and Asia.
Charlie has been a committed volunteer at Upper Canada College for decades, serving as a member of UCC’s Campaign Cabinet, a member of the Board of Governors, a member of the UCC Foundation Board of Trustees, as well as various committees and subcommittees. His nominators referred to Charlie as “the glue that connects the Class of 1980, even 45 years after graduation.”
He has also given his time and expertise to other organizations, such as Holland Bloorview Kids Rehabilitation Hospital, Havergal College Foundation and the Huntington Society of Canada, and is the founding member and chairman of the V-42 Foundation, which helps active and retired members of the Canadian Special Operations Forces.
As one of his nominators noted, “Charlie’s clarity, discipline and steady judgment have strengthened the College’s financial stewardship, and his enduring commitment to UCC, from governance to philanthropy, exemplifies the very spirit of this award.” His leadership and collaborative skills were praised. “He effects good governance, and change when necessary, through collaboration and earning people’s trust. It’s a remarkable skill and the College has been the fortunate beneficiary.”
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