#4. Cam Ward (2002 NHL Entry Draft, 1st Round, 25th Overall)
Toronto’s Actual Pick: 1st Round, 24th Overall (Alexander Steen)
Would Cam Ward have came in as a rookie and won a Stanley Cup with the Toronto Maple Leafs like he did with the Carolina Hurricanes? Probably not, but a man can dream.
The Leafs selection of Steen here was great value. In terms of players from that draft class, he has the sixth most career games played. Although the Leafs traded him far too early in his career, they made a great decision in drafting him.
Steen was a great selection, but Ward could have been more useful. Ward has 334 career NHL wins and over 700 career games played. He was one of the most consistent goaltenders in the NHL and would have been very beneficial to the Leafs in a time where they had no consistency in net.
The Leafs goaltenders during Ward’s prime of 2005-to-2015 were a joke. Whether it was Andrew Raycroft, Vesa Toskala, James Reimer or Jonathan Bernier, neither of these goaltenders could get the job done when it mattered.
Ward could have been the savior to Leafs goaltending problems for years, but unfortunately that wasn’t the case for Leafs’ fans.
#3. T.J. Oshie (2005 NHL Entry Draft, 1st Round, 25th Overall)
Toronto’s Actual Pick: 1st Round, 21st Overall (Tuukka Rask)
If we look back at the 2005 NHL Entry Draft, the Leafs made the right selection with Rask, but in hindsight TJ Oshie would have been better.
If the Leafs never picked Rask, he would have made this list as one of the biggest misses in Leafs history. However, by drafting him and trading him before he made the NHL, that’s even more of a blunder than not drafting him at all.
Oshie on the other hand is a steady right-winger who can help out any team offensively. During his time with the St. Louis Blues, he was a fan-favourite averaging between 45-to-60 points each season. He always had potential for a break-out season, but that didn’t come until his opportunity with the Washington Capitals.
On a team hungry for a Stanley Cup, Oshie had a career high 33 goals in 2016-17, but made his mark during the 2017-18 playoffs. Right behind the top three European forwards of Evgeny Kuznestov, Alex Ovechkin and Nicklas Backstrom, Oshie was fourth on the team in playoff scoring finishing with 21 points in 24 games.
Oshie was a key addition to helping Washington get over the hump and win their first ever Stanley Cup.
Over the last few seasons, Oshie has proved to be a consistent 20-goal scorer and someone who is a perfect second-line winger. If things went differently, Oshie and Phil Kessel could have made a great 1-2 punch at right-wing for the Leafs.