Speaking on his weekly Coaches Corner segment on Hockey Night in Canada, Cherry was supportive of Kadri and says the way the 24-year-old forward has been treated by the Toronto organization may cost the club his services in the future.
"He's been ridiculed, humiliated and finally they sat him out — big deal," said Cherry.
"The kid is not going to be here in two years, he'd be nuts. Being humiliated in front of his family, he's been called everything since he came here. I am betting you any money he'll stay here when he's restricted. The day he (becomes) unrestricted, they better trade him before, because he'll be gone."
The Maple Leafs originally made Kadri a healthy scratch for Monday's game against the New York Islanders after showing up late for a team meeting on Sunday. The centre said he had apologized to teammates and coaches for what he called an "uncharacteristic" mistake.
But on Wednesday, Leafs president Brendan Shanahan extended Kadri's suspension to the next two games, saying the London, Ont., native's problems went beyond being late for Sunday's meeting.
Kadri returned to the Leafs lineup Saturday against the Vancouver Canucks. He becomes a restricted free-agent this summer and will need a new contract. He hits unrestricted free-agent status in the summer of 2017.
Kadri has had his share of criticism and controversy since Toronto drafted him in 2009.
His first two seasons as a pro were spent between the Leafs and their American Hockey League affiliate Toronto Marlies — with former Leafs head coach Ron Wilson often citing Kadri's two-way play as the reason why he needed more time in the minors.
In 2012 he showed up to training camp, after spending the summer training with fitness guru Gary Roberts, and was questioned about his body-fat percentages by then Marlies head coach Dallas Eakins.
"There's been a cloud over this kid ever since he was 18 years old," said Cherry. "I remember his first training camp, he led the team in goals, assists and they said he couldn't play defence (but) he was plus-6. (They) didn't give him a chance and he was sent down."