Cherry spoke out against the Pittsburgh Penguins captain Saturday during his weekly "Coach's Corner" segment on CBC's Hockey Night in Canada. He joined the chorus of critics who claim Crosby is a cheap player who whines to the referees.
"A long time ago when Crosby was coming out I tried to warn him 'quit diving, quit whining,' I was the worst guy in the world ... and all I was trying to do was help him," Cherry said.
"All I said was stop whining, stop diving and snapping the head back."
Cherry says that Crosby is being targeted by opponents because they don't respect him.
The former Boston Bruins coach said that Crosby has to learn to rise above the physical play of his opponents, or he will get injured.
"If you want to survive in this league, he's got to suck it up and stop getting stupid penalties and going back at guys," Cherry said.
Crosby has struggled with head and neck injuries over the past two seasons.
Cherry showed a clip of Crosby giving Philadelphia forward Brayden Schenn a retaliatory shot in a game last Sunday. Schenn later replied with a cross-check to Crosby's back, an incident which was partly responsible for touching off a line brawl between the two teams in the game's dying minutes.
Cherry said Crosby shouldn't have retaliated against Schenn.
"Listen, I admire him, but he should be like (Montreal great) Guy Lafleur," Cherry said. "All you have to do is look at (Tampa Bay star Steven) Stamkos, he gets more abuse than anybody. You cannot be the greatest player in the world and expect to get a free ride. And what you've done, you've turned the league and teams against you."
Earlier this week, New York Rangers coach John Tortorella, Philadelphia assistant Craig Berube and former NHL coach turned TV analyst Mike Milbury all took turns accusing Pittsburgh of being one of the dirtiest teams in the league. Tortorella was fined US$20,000 for his comments.
All three had choice words for Crosby, while Tortorella and Berube also showed disdain for the Penguins' other superstar, Evgeni Malkin.
Milbury started the avalanche of criticism on Monday, calling out Crosby on a Philadelphia radio station.
"So you know, Crosby gets cross-checked, big whoop," Milbury said. "He said after he came back from his 35th concussion, 'I'm not going to do this anymore, I'm not going to get into this scrums, I'm going to stay away from that stuff.' He couldn't help himself because there's a little punk in Crosby."
Milbury later apologized for his comments.
On Tuesday, Berube picked up where Milbury left off. Speaking on CSN Philly Daily News Live, Berube called Crosby and Malkin "the two dirtiest players on their hockey team."
"I've got no problem with what Schenn does," he added. "And if somebody runs (Crosby) over, that's great. They should run him over."
Tortorella's comments came after the Penguins' 5-2 win over the Rangers on Thursday, which included a knee-on-knee hit by Pittsburgh defenceman Brooks Orpik on New York forward Derek Stepan.
"It's a cheap, dirty hit," Tortorella said. "I wonder what would happen if we did it to their two whining stars (Crosby and Malkin) over there. I wonder what would happen. So I'm anxious to see what happens with the league with this. Just no respect amongst players. None. It's sickening."