The Toronto Maple Leafs of the late 1990’s weren’t a long term planning team. They were a team looking to win a Stanley Cup and were going to flex their financial muscles rather than their scouting skills to do so.
Leading up to the 1999 draft, the 1996 and 97 drafts saw no first round picks available, and only a couple players picked would become NHL mainstays: Shawn Thornton, Tomas Kaberle, Adam Mair. In 1998 the Leafs picked long time Maple Leafs Nik Antropov in the first round, and Alexei Ponikarovsky in the fourth.