York first wrote for The Globe as a teenager in 1974, after a reporter who visited his class recruited him to write about amateur sports. Not long afterwards, popular Globe sports columnist Dick Beddoes took York under his wing and became his mentor.
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. In 1982, his nickname among some CFL fans was "the enemy." In 1993, former Blue Jays' star George Bell reportedly lost his temper when York was questioning him, angrily exclaiming that York should "get the hell over to Saskatchewan or Calgary and cover Canadian football like you're supposed to."
While on assignment in 1989, York was in the upper deck of San Francisco's Candlestick Park, preparing to cover the World Series between the San Francisco Giants and the Oakland Athletics, when the deadly Loma Prieta earthquake struck. York escaped unscathed but witnessed the horrible aftermath of the tragedy.
York went on the record in 1989 correctly predicting that Cito Gaston would be hired as the Blue Jays permanent manager.
In 1990, York reported that hockey legend Bobby Orr had become a pariah at York University's sports clinic after he stopped supporting their efforts. York claimed that the clinic subsequently wanted nothing to do with Orr.
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. 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.
In 2015 and 2016, York criticized then-Blue Jays star Jose Bautista for his infamous "bat flip" after a game-winning home run in the 2015 ALDS. He called Bautista a poor sport, accused him of violating the norms of baseball etiquette, and also called him "evil" for his disrespectful treatment of reporter Steve Simmons. 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.
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. When B'nai Brith went public with its findings, the Liberal Party dropped Guillet as a candidate. The story received considerable national media coverage.