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Top 10 Toronto Maple Leafs Draft Misses: 2000s Edition

By Stephen Nixon

WASHINGTON, DC - APRIL 13: Justin Williams #14 of the Washington Capitals scores a goal against the Toronto Maple Leafs in the first period in Game One of the Eastern Conference First Round during the 2017 NHL Stanley Cup Playoffs at Verizon Center on April 13, 2017 in Washington, DC. (Photo by Patrick Smith/Getty Images)
WASHINGTON, DC - APRIL 13: Justin Williams #14 of the Washington Capitals scores a goal against the Toronto Maple Leafs in the first period in Game One of the Eastern Conference First Round during the 2017 NHL Stanley Cup Playoffs at Verizon Center on April 13, 2017 in Washington, DC. (Photo by Patrick Smith/Getty Images) /
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LOS ANGELES, CA – JUNE 13: Justin Williams #14 of the Los Angeles Kings . (Photo by Bruce Bennett/Getty Images)
LOS ANGELES, CA – JUNE 13: Justin Williams #14 of the Los Angeles Kings . (Photo by Bruce Bennett/Getty Images) /

#2. Ben Bishop (2005 NHL Entry Draft, 3rd Round 85th Overall)

Toronto’s Actual Pick: 3rd Round, 82nd Overall (Phil Oreskovic)

Although it’s unlikely that the Leafs would have picked another goaltender in this draft after selecting Tuukka Rask earlier in the draft, this is all a ‘what-if’ scenario so let’s assume they should have.

With the Leafs real selection in this draft, they went with Phil Oreskovic. I don’t want to say anything bad about him because just look at his HockeyDB page. He is one scary dude and at 6-foot-four, 240 pounds, I don’t want to mess with him.

Let’s just say his career didn’t work out and move onto Ben Bishop.

Bishop is a world-class goaltender but is surprisingly on his sixth NHL team already. After being drafted in St. Louis, then moved to Ottawa, Bishop never saw an opportunity until his time with Tampa Bay.

Bishop was spectacular with the Lightning and helped guide his team to a Stanley Cup Final in the 2014-15 season. Although he was playing as a number-one goaltender, the team decided to move on from him and kept Andrei Vasilevskiy as their starting goalie instead.

It was definitely the right move, but Bishop has continued to be one of the best goaltenders in the NHL with his newest team, the Dallas Stars. In 2018-19, Bishop was named a finalist for the Vezina trophy for the third time in his career after posting a 2.09 GAA and a career best .934 SV%.

Bishop could have been a great alternative to the mediocrity of goaltenders that Toronto had in the 2010s, so it’s unfortunate the team missed out on him in the 2005 NHL Entry Draft.

#1. Justin Williams

Toronto’s Actual Pick: 1st Round, 24th Overall (Brad Boyes)

For a Leafs franchise that has been tormented by Game 7’s over the past decade, they could have used “Mr. Game 7” Justin Williams.

Williams was a great player in the regular season but it felt that he took it to a whole new level once the playoffs started. With a mindset like that, it’s no surprise that he has three Stanley Cup championships.

Not only does he have three rings, but he was awarded as the Conn Smythe Trophy winner during Los Angeles’ cup run in 2013-14. With 25 points in 26 playoff games, Williams was spectacular during that stretch and much deserving of that award.

With 1264 career NHL games played, Williams’ career is essentially finished having already retired once before returning for 20 games this year. Within that career, he has 320 goals and 797 points.

He never scored more than 67 points in a regular season, but his leadership was something that couldn’t be measured.

Next. 1990s Toronto Maple Leafs Draft Misses. dark

Although his career may not have been filled with as many trophies if he were drafted to Toronto, I’m sure the Cobourg, Ontario native would have provided many of memorable moments for Toronto Maple Leafs fans.

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