For a team with the history of the Montreal Canadiens, they are not without their fair share of draft-day misses. The Canadiens have a long list of draft busts, but this article will focus on the biggest draft mistake in Canadiens' history. It will not just be about how well they performed for the Canadiens, but also the players they missed out on by selecting him.
If it were purely on how they performed for the Canadiens, the easy selection would be David Fischer, who they took 20th overall in 2006, missing out on players like Claude Giroux, Nick Foligno, and Brad Marchand. Fischer never played a game for the Canadiens, while the others became future NHL all-stars.
While Fischer's lack of impact makes him the easy answer for the biggest draft mistake, a deeper look reveals a more damaging pick: Andrei Kostitsyn. Fischer was the worse of the two players, that is for sure, but the players drafted after Kostitsyn were the type of guys you build franchises around. While Kostitsyn showed flashes of top-six talent, we never got to see him reach his full potential.
Kostitsyn had three 20-goal seasons in Montreal, showing real promise, but his flame died out fast. The Canadiens traded him to Nashville during the 2011–12 season, and he never returned to the NHL afterward. He had a lot of potential, with a shot that could have made him a legitimate 30-goal scorer, which makes it all the more disappointing, considering how stacked the 2003 NHL Draft was.
The 2003 NHL Draft produced a remarkable number of future Hall of Famers and perennial All-Stars. The biggest name the Canadiens missed out on was someone who eventually was selected by the team's biggest rival. Patrice Bergeron is a future no-doubt Hall of Famer. He is one of the best, if not the best, defensive forwards in NHL history.
However, it is not fair to blame the Canadiens for not selecting him in the first round, as every other team decided to pass on him. The same goes for Shea Weber not being on the list. It has more to do with the other players selected in the first round that makes the Kostitsyn pick a mistake on their part.
1. Zach Parise

If the need for the Canadiens at the time was a scoring winger, there were a lot of good ones still available for Montreal with the 10th pick. Zach Parise was one of those options. In his prime, he was one of the best offensive players in the league. He was a consistent 60-70 point-a-season guy, with a real scoring touch, scoring 30-plus goals in six seasons. He dealt with injuries once he left the New Jersey Devils, but was still a good top-six winger with the Minnesota Wild.
2. Corey Perry

Another elite winger available later in the first round eventually found his way to Montreal, Corey Perry. In his prime, he was an automatic 30-goal-a-year player, scoring a career high 50 in 2010-11, where he also took home the Hart Memorial and the Rocket Richard Trophy. Even at 40 years old, he remains a reliable contributor, continuing to cause havoc in front of the net like few others can.
3. Ryan Getzlaf

Montreal has always needed a first-line centre, and Ryan Getzlaf would have fit the mould for the type of centre they would have been looking for. Getzlaf was a big, physical, two-way centre who was as consistent as they come. He was a regular 70-point-a-season player who was a true leader, captaining the Anaheim Ducks for 12 seasons. In just his second season, he was a crucial member of the Ducks' 2007 Stanley Cup-winning team, contributing seven goals and 17 points in 21 games.
4. Brent Burns

Brent Burns was originally drafted as a winger but later became a Norris Trophy-winning defenceman. He was a force on the blueline during his career, but his offence exploded once he got to the San Jose Sharks. During his prime, he was arguably the second-best offensive defenceman in the league, just behind Erik Karlsson. His goalscoring ability from the blueline, though, was second to none. He has 13 seasons of scoring 10-plus goals and a career high of 29 in 2016-17.
While Kostitsyn's career was not a complete failure, the fact that so many future stars were drafted immediately after him makes his selection arguably one of the most damaging draft mistakes in Canadiens history. The course of the Canadiens' history in the late 2000s and early 2010s might have looked very different if they had gotten that pick right. One pick can not guarantee a Stanley Cup, but it would have made the chase for it a lot easier.