[5] He began his journalistic career as a young reporter and summer staffer for The Globe and Mail, covering both sports and news during his high school and university days.
[1] After his graduation, then-Globe managing editor Clark Davey hired York full-time for sports coverage and asked him to inject objective and tough reporting into his work.
One such example occurred when he discovered that Toronto Blue Jays star Kelly Gruber was spending time water-skiing and playing tennis in Northern Ontario, while simultaneously missing games on and sitting out on his team's injured list.
York continued to criticize Bautista after Texas Rangers player Rougned Odor punched him in the face the following season, believed by many to be in retaliation for the bat flip incident.
[2][15][16] York at times reported hostile treatment from athletes, including incidents where he said Blue Jays players threw items such as socks and food at him during team flights.
[19] York sparked another controversy in 2006 when he claimed that Toronto Raptors players were secretly rooting to see their coach, Sam Mitchell, ousted from the job.
[20] In recent years, York repeatedly claimed on Twitter that Blue Jays manager John Gibbons would imminently be fired—something he later acknowledged was at least in part meant as a joke.
[23] In January, 2016, York was appointed to the dual role of Senior Coordinator of Media and Sports for B'nai Brith Canada, the country's oldest Jewish human-rights organization.
[24][25] In 2019, during York's time as Director of Communications, B'nai Brith unearthed a series of controversial comments and social media posts made by Hassan Guillet, a parliamentary candidate for the Liberal Party in that year's Canadian federal election.
[26][27][28] York spoke to the media on B'nai Brith's behalf when the organization successfully advocated for the firing of Ryerson University teaching assistant Ayman Elkasrawy, who was accused of making antisemitic remarks in the classroom.