Osmington Inc. appoints David Chaikof, John Tory and Phillip Crawley as Senior Strategic Advisors

TORONTO , Jan. 27, 2026 /CNW/ - Osmington Inc., a private investment company founded and controlled by David Thomson, Chairman, Thomson Reuters announces the appointment of David Chaikof, John Tory and Phillip Crawley as Senior Strategic Advisors.

David Chaikof spent his career at Torys specializing in M&A, corporate governance, private equity and capital markets work across Canada and the US. David guided blue chip public and private companies and their boards of directors through complex and transformative transactions. His distinguished legal career also included several leadership roles - most recently as the managing partner of Torys New York office.  David's broad deal experience, deep insight and long-standing relationships with business leaders will be a great asset to Osmington. David will advise Osmington on investment structuring and strategic capital partnerships.

John Tory, who joined Osmington in September 2023, has enjoyed a multi-faceted career as a lawyer, chief executive, corporate director, broadcaster and from 2014 to 2023 served as Mayor of Toronto, North America's 4th largest city. Equally important to John has been his volunteer involvement in the community whether as a founder and Chair of Civic Action, volunteer Chair and Commissioner of the Canadian Football League, Chair of the Toronto United Way campaign, Chair of three campaigns for St. Michael's Hospital or Chair of the capital campaign for the TIFF Bell Lightbox. As Mayor he oversaw the achievement of an unprecedented $40 billion three government transit agreement, significant new housing initiatives, a passionate commitment to the unity of the City, a deep respect for its diversity and a commitment to sound financial management. John was also a champion for the City's economy, campaigning for investment especially in the fast-growing tech and financial services sectors and was a committed and reliable partner for the Arts and Film sectors, among many others.

Phillip Crawley, former Publisher and CEO of The Globe and Mail, brings more than two decades of experience leading one of Canada's most influential media organizations. He oversaw major digital transformation, organizational restructuring, and national editorial positioning during his tenure. He is chair of The Globe Foundation and immediate past chair of Sunnybrook Hospital Foundation in Toronto. With a track record of guiding large enterprises through industry disruption, Phillip offers deep communication, strategy, and leadership expertise.

"We are thrilled to welcome David, John and Phillip to our team," said Lawrence Zucker, CEO of Osmington Inc. "Each brings an extraordinary depth of experience and leadership across business, law, public service, media, and corporate strategy. Beyond their business experience, their integrity and strength of character are qualities that make these individuals a valuable addition to our organization. Their perspectives are already contributing meaningfully as Osmington continues to grow its platform and pursue ambitious opportunities across Canada. We look forward to benefiting from their deep expertise."

About Osmington 

Osmington Inc. is a private investment company founded and controlled by David Thomson, Chair of Thomson Reuters. Osmington is led by Lawrence Zucker and its focus is on value creation from investment activities in a broad range of asset classes including private equity, real estate and venture capital. Signature projects for Osmington include the redevelopment of Union Station and the purchase and relocation of the Winnipeg Jets. 

For more information, visit www.osmingtoncp.com

SOURCE Osmington Inc.

Media Contact: Dina Conte-Vari, [email protected]