It’s personal for new United Way boss
‘I would not be who I am today without United Way’: Matthew Cutler
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The newly hired president and CEO of United Way Winnipeg knows the agency can help change lives — his was one of them.
Matthew Cutler, currently the vice-president of exhibitions at the Canadian Museum for Human Rights, and before that the province’s assistant deputy minister of communications and engagement, has been chosen to take the reins of the organization as of Aug. 11.
“I would not be who I am today without United Way,” Cutler said on Wednesday.

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Matthew Cutler, current vice-president of exhibitions at the Canadian Museum for Human Rights, has been chosen to be the next CEO of United Way Winnipeg, starting Aug. 11.
“Growing up, accessing United Way services as a young person, whether it was because of mental health issues, or experiencing poverty as a family, accessing food banks and other resources and then, when I came to Winnipeg, I knew the first place I needed to go was the United Way. If I wanted to understand the city and really get a sense of the fabric of the place, so it was my first stop.”
Cutler became an agency liaison volunteer and, during his roles with both the museum and the province, he served as executive champion of the United Way.
Asked about his immediate plans for United Way, he said it has “a very exciting strategic plan” that was developed to help celebrate its 60th anniversary.
“I think the real question is: what do the next 60 years hold?” he said.
“We know, and we don’t have to look hard, when we walk the streets of the city, poverty, mental health, there are affordability issues that are affecting the fabric of our community. The United Way model of bringing folks together and working united is one of the key solutions to these challenges.”
The position became vacant when Michael Richardson stepped down earlier this year. In the interim, the agency has been helmed by Richardson’s predecessor, Connie Walker.
Cutler was born and raised in Ontario, where he admits “I grew up with pretty modest means.”
“Then… mental health services were so key for me when I was coming out as a queer person as a young person.”
Cutler began working in marketing and communications for the Niagara Centre for Independent Living, before going to Central Toronto Youth Services. From there, he spent six years as director of strategic partnership initiatives with The 519, serving as its project director and chief staff officer of the PrideHouse Toronto Initiative.
Cutler then worked for the City of Toronto as part of the senior management team of its parks, forestry and recreation section.
Cutler said when his partner was appointed to the University of Manitoba faculty, he followed him to Winnipeg.
Here, Cutler became assistant deputy minister in 2019, and also served as the lead for the provincial government’s coordinating team on COVID-19.
He was hired by the museum in August 2022.
Cutler has volunteered extensively, including as chair of the board of the Rainbow Resource Centre since 2019, a board trustee with the United Way since 2019, and special adviser to the board of the Institute of Public Administration of Canada.
He received a master’s degree in leadership from Royal Roads University in November.
kevin.rollason@freepress.mb.ca

Kevin Rollason is a general assignment reporter at the Free Press. He graduated from Western University with a Masters of Journalism in 1985 and worked at the Winnipeg Sun until 1988, when he joined the Free Press. He has served as the Free Press’s city hall and law courts reporter and has won several awards, including a National Newspaper Award. Read more about Kevin.
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Updated on Wednesday, July 2, 2025 5:17 PM CDT: Updates photo