A sleeping bag and a piece of cardboard.

That’s all the comfort Maple Leaf Sports and Entertainment CEO Tim Leiweke will be afforded as he joins 73 corporate and community leaders braving sub-zero temperatures at the Covenant House Executive Sleep Out, Thursday night in downtown Toronto.

The event supports $20 million in programs to provide shelter, food, education and support to the estimated 3,000 youths without shelter who turn to Covenant House every year.

For Leiweke the event holds a special relevance. He was 12-years-old when his mother’s death from cancer jolted a middle-class family that included five other siblings. About half of homeless kids come from middle or upper-middle income families.

“If not for the health of my father we probably would have been in a situation like the one these kids find themselves in,” he said. “So what I understand is all of us are very lucky to have a roof over our head, families around us who are there to support us in times of need and a system for people who, through no fault of their own, need our help.”

As a CEO in Los Angeles, Leiweke was involved in that city’s Midnight Mission program for the homeless but the impact of Toronto’s cold temperatures heightens the risk for every single homeless person, he said.

“We get to show up with layered clothing and nice coats and nice sleeping bags but that really doesn’t give us the experience of what it’s like to be in a young homeless person’s shoes,” Leiweke said.

“What hopefully we are doing tonight is creating some awareness, raising some money and emphasizing that the people who have to use this service, whether it be because of health, abuse  or economics do so because of circumstances they did not choose.”

Last year’s inaugural event generated $530,000 for Covenant House and organizers are hoping this year’s sleep out will raise upwards of $650,000.

“This money this event generates will help us provide 94 young people with a month and a half of safe shelter, food, clothing, all the basics as well as our support programs like our school and jobs training,” said Covenant House Communications Manager Rose Cino.

“It can really help kids get started on turning their lives around.”