Feb. 22, 1998 — Cherry criticized Canada's choice of skier Jean-Luc Brassard as Olympic flag-bearer, calling him "a French guy, some skier nobody knows about." The CBC ombudsman would later rule that Cherry's comments crossed the line. CBC had rights to Hockey Night in Canada and Coach's Corner — Cherry's most recognizable media platforms — until the 2014-15 NHL season.
March 22, 2003 — Cherry entered into a heated debate with Coach's Corner co-host Ron MacLean about Canada's failure to join the war in Iraq. The debate and Cherry's pro-U.S. sentiments prompted at least 1,500 complaints to the CBC.
Jan. 24, 2004 — Cherry went on a rant about visors in the NHL, which prompted the commentator to say the protective gear was worn by wimps and usually sported by "Europeans and French guys."
The comments were taken as a slur against francophone Canadians, touched off criticism from numerous federal politicians and forced the CBC to temporarily implement a seven-second tape delay on his segments.
Dec. 7, 2010 — Wearing a garish pink suit, Cherry crashed Rob Ford's inauguration as mayor of Toronto with zeal that seemed to surprise even Ford. Cherry was invited by Ford to attend the ceremony and put the chain of office around Ford's neck.
He took the opportunity to deliver a three-minute tirade in front of city council, calling bicycle riders "pinkos" and celebrating Ford's election with the phrase "put that in your pipe you left-wing kooks."
Oct. 6, 2011 — Cherry, an avowed supporter of fighting in hockey, called former enforcers Stu Grimson, Chris Nilan and Jim Thomson "pukes" and "turncoats" for suggesting that NHL players who fight are prone to substance abuse. The comments were made shortly after the deaths of Derek Boogaard, Rick Rypien and Wade Belak, three former NHLers known for fighting.
April 28, 2013 — Cherry said he was against women reporters being allowed in NHL dressing rooms.
"I remember the first time it happened to me," Cherry said. "Guys are walking around naked and I hear this woman's voice. I turn around and she's asking me about the power play. I say, 'Let's go outside.' She said, 'I'm not embarrassed.' I said, 'I am."'
Several women reporters and the Association for Women in Sports Media rebuked Cherry for his stance.
Feb. 7, 2015 — Cherry faced backlash and a call for an apology from some Inuit Canadians when, while on location in Newfoundland and Labrador, he called MacLean a "savage" and a "barbarian" for eating seal meat.
Cherry walked back his comments a couple of days later. "I have no problem with my friends who are hunters and eat venison and duck. Just the same, as I have no problem, with people who hunt seals and seal meat," Cherry said on social media.
"I do however find it very unusual, in my world, that a person would go into a restaurant and order a seal burger for lunch. I meant no disrespect to the hunters who hunt and eat seal meat just like I have no disrespect for the hunters who hunt deer and duck and eat their meat."
Feb. 3, 2018 — Citing cold weather during winter, Cherry sounded off against those looking to combat climate change during a segment of Coach's Corner.
Cherry asked MacLean if he and his "left-wing pinko friends" could explain their concerns over rising global temperatures while Toronto was experiencing a midwinter cold snap. "I'm just asking you, the cuckaloos are always saying there are warming trends," Cherry said. "We're freezing to death."
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