Cholowski, an offense-minded defenseman from Langley, British Columbia, started his NHL career on a high note, scoring a goal for the Detroit Red Wings in his first game, against the Columbus Blue Jackets, on Oct. 4, 2018. In his second game, three nights later, he had two assists against the Los Angeles Kings.
The Red Wings selected Cholowski in the first round (No. 20) of the 2016 NHL Draft after his second full season with Chilliwack of the British Columbia Hockey League. He played for St. Cloud State in 2016-17, then signed a pro contract with the Red Wings on April 5, 2017. He split the 2017-18 season between Prince George and Portland of the Western Hockey League.