A native of Chatham, NJ, O’Connor played for the Dartmouth Big Green at Dartmouth College, in Hanover, New Hampshire. During his freshman season, O’Connor recorded seventeen goals and nine assists for twenty-six points in thirty-four games. Following an outstanding freshman season, he finished the 2019–20 season with twenty-one goals and twelve assists for thirty-three points in thirty-one games, earning him Ivy League Co-Player of the year. On March 10, 2020, O’Connor was signed as an undrafted free agent by the Pittsburgh Penguins to a two-year, entry-level contract. Drew is a big rangy forward with elite skill and skating with the potential to be a strong NHL power forward in the years to come.