#6. Peter Sykora (1995 NHL Entry Draft, 1st Round, 18th Overall)
Toronto’s Actual Pick: 1st Round, 15th Overall (Jeff Ware)
Fun fact: Did you know that there was another Peter Sykora from Czech Republic who was drafted in the 1997 NHL Entry Draft?
That’s not important, but I found it interesting.
Anyway, the Leafs missed out big with this pick. They drafted Jeff Ware who played 21 NHL games, when they could have got Sykora who played over 1000 NHL games.
It took Sykora a few years to get settled into North American professional hockey, but when he found his groove, he was outstanding. From 1998-to-2004, Sykora had six straight seasons of 20-plus goals, including a 35-goal season in 2000-01.
It felt as if wherever Sykora went, the team found success. Within his career, he made it to six Stanley Cup Finals and was victorious twice. Once with the New Jersey Devils in the 1999-00 season and a second time with the Pittsburgh Penguins in 2008-09.
Sykora would have been a very nice addition to the Leafs line-up in the late 90s and early 2000s, but instead the team got nothing in return from picking Ware.
#5. Alex Tanguay (1998 NHL Entry Draft, 1st Round, 12th Overall)
Toronto’s Actual Pick: 1st Round, 10th Overall (Nikolai Antropov)
The Leafs didn’t completely mess up their pick by drafting Antropov 10th overall, but they could have been better off with Tanguay.
Tanguay was a great player and found himself situated in an even greater spot by getting drafted to Colorado. Tanguay joined a team that was already stacked with talent, but was able to play a key piece in the team’s Stanley Cup victory.
During their Stanley Cup win in the 2000-01 season, Tanguay had 21 points in 23 games and scored the game-winning goal in Game 7 of the Finals. In only his second season in the NHL, Tanguay was already beloved by Avalanche fans and making a name of himself.
Although Tanguay would eventually play with five NHL teams in his career, the majority of his time came in Colorado.
His offensive numbers would dip as his career went on, but in 1088 NHL games, he still managed to score 863 points.
Tanguay’s speed was always a threat and although Antropov ended up being a good Leaf, Tanguay’s presence would have been more beneficial for a Toronto Maple Leafs team that was so close to a Stanley Cup Final in the early 2000s.