Jeff Ware was aggregiously bad for the Leafs. Apparently he was drafted in the first round by Cliff Fletcher because Ware's dad was a friend.
So while other teams were busy drafting for the future, he was picking a kid with zero upside because of family ties.
Ware's family was friends with Bill Watters who was part of Toronto's assistant GM: http://articles.sun-sentinel.com/1999-04-11/sports/9904110004_1_florida-panthers-maple-leafs-toronto
It was a controversial decision to draft Ware so high four years ago. The Toronto media criticized the deal because Petr Sykora was still there for the taking, accusing the Maple Leafs of just picking a local kid who was neighbors with Bill Watters, now the Leafs assistant to President Ken Dryden.
http://www.hockeysfuture.com/articles/302/maple_leafs_training_camp_report/
Jeff Ware – 21, 6’4″ 220 lbs – Quick, name three Maple Leaf first round picks who are still with the organization! Antropov is only the second, the other being Jeff Ware. One of the factors that led to the dismissal of Cliff Fletcher was the popular belief that Ware had been drafted because of his father’s friendship with assistant GM Bill Watters, who is still with the organization.
If I recall correctly, Watters had kid(s) in the same school as Ware and personally vouched for his character. I'll have to check the old THN rankings to see if the Ware pick was off the board.