Drafted by the Calgary Flames, MacDonald chose to attend Harvard University, where he graduated with four school scoring records (including career goals), and ranking in the top five in 11 different statistical categories; he studied philosophy under the tutelage of Alexander George.

MacDonald was a member of the bronze-medal winning American team at the 1986 World Junior Hockey Championship.

[1] He took a year off from Harvard in 1987-88 to play member of the United States' 1988 Winter Olympics team in Calgary.

After college, he played for HC Lugano is the Swiss League before recurring migraine headaches forced him to retire.

He then went to Stanford Business School and is now a general partner in a Boston-area private equity firm, where he lives with his wife and three children.