On October 5, 2021 Madsen passed away. He had stepped down as executive director of the Cheer Board earlier in the year, replaced by Shawna Bell.
“My earliest memories of the Cheer Board were of Kai and the overwhelming warmth and kindness that he brought to the holidays every year. It is a sad day for Winnipeg. Kai will be missed by so many across the city,” said Bell.
Madsen’s tenure with the CCB goes back more than 50 years. He worked with the board as a volunteer and then became its executive director, a post he held for more than 25 Christmas seasons.
Kai’s presence with the Cheer Board was much more than that of an executive. His face had nearly become that of Christmas itself in Winnipeg, many media outlets echoed that thought. Just ask Winnipeggers who received holiday hampers, they would agree.
In recognition of Kai's commitment to the Cheer Board, a scholarship benefitting inner-city youth was created in 2022. This scholarship is administered by The Winnipeg Foundation on an annual basis.