In over 100 years of existence, the Montreal Canadiens have had the most success in the NHL's history with 24 Stanley Cups, a great deal of winning seasons and legendary players. With some of the loudest and most passionate hockey fans in the entire league, the Canadiens are constantly put under the pressure of succeeding every season in order to keep their fanbase satisfied. The same can be said about their trades and free agent signings.
The Habs have brought in tons of players through trades and signings over the years; some good, some bad. As we know, the Canadiens have made trades that have come back to bite them whether it be trading a young prospect who developed into a top player or acquiring players that didn't pan out. The historical franchise has been a part of some of the biggest trades recently which many fans questioning the organization's intelligence. Nonetheless, it's no secret that this team has let go of some players they never should have or put too much faith in players who had absolutely no hope.
That said, let's take a look at eight players the Canadiens should have never let go, and seven that they held on to for too long.
15 Too Soon: Mikhail Sergachev
This past June the Montreal Canadiens made a blockbuster deal sending highly regarded prospect Mikhail Sergachev to the Tampa Bay Lightning in exchange for Jonathan Drouin. Many have their own different opinions about who won this trade from the start. At this point, there are still unanswered questions that cannot be answered until this trade plays out in the future.
There's no question that the Canadiens get a much-needed young and talented forward in Jonathan Drouin. However, the risk of giving up a potential elite top-2 defenseman might come back to haunt the Canadiens in the future. Giving up a top prospect less than a year after drafting him is not something every GM would be quick to pull the trigger on, which makes this a questionable trade for Marc Bergevin.
14 Too Long: David Desharnais
The Canadiens brought in David Desharnais by signing him as an undrafted player in 2008. Desharnais saw his best season come in 2011-12, where he recorded 60 points in 81 games. The Habs have been searching for their top centreman for a while now. Desharnais was the team's top centre for some time after showing great chemistry with winger Max Pacioretty. Despite the Quebec native's ability to mesh with the team's top scorer, Desharnais didn't seem to have any other value to the Canadiens and was often one of the weaker players on the ice if separated from Pacioretty.
Many Habs fans would tell you that Desharnais got more ice-time than he deserved under head coach Michel Therrien, which prevented younger and better players from gaining more ice-time. Towards the end of his tenure with the Habs, the undrafted forward found himself often being a healthy scratch. Desharnais was traded to the Edmonton Oilers during last season's trade deadline for Brandon Davidson.
13 Too Soon: Mike Ribeiro
Mike Ribeiro was drafted in the second round by the Canadiens in 1998 draft. Ribeiro, a native of Montreal, split time with the AHL and NHL for a few seasons before playing a full season with the team in 2003-04 and scored 65 points that season. However, Ribeiro found himself getting into some trouble off the ice. He was apparently involved in drugs and alcohol with teammates Jose Theodore and Pierre Dagenais. Much to the dismay of the team's management, the "Three Amigos" were eventually separated. Ribeiro was traded to the Dallas Stars just before the start of the 2006-07 season for nothing more than Janne Niinimaa.
While Ribeiro was starting to become a problem off-ice, the Canadiens pulled the trigger far too easily and didn't even come close to receiving equal value in return for the young forward. The Montreal native turned his career around and notched 793 points in over 1,000 career games. Perhaps the Canadiens should have been a little more patient with the young Montrealer and allowed him to learn from his mistakes instead of going for the quick solution.
12 Too Long: Andrei Kostitsyn
The Canadiens regret picking Andrei Kostitsyn 10th overall in the 2003 NHL draft. Selected over guys like Jeff Carter, Brent Seabrook, and Ryan Getzlaf, Kostitsyn showed tons of goal-scoring potential which caught the attention of the franchise, but unfortunately was never able to reach expected heights. The Belarussian took part in seven seasons with the Canadiens. He had a career-season in 2007-08 scoring 26 goals and 53 points, but was never able to take his game to the level of a top-1o draft pick.
Kostitsyn was often criticized by Habs media and fans for his apparent laziness and tendency to disappear during games. With early signs showing that Kostitsyn was not going to be a top player, the Habs failed to trade him soon enough to get a valuable asset in return. He was eventually traded to the Nashville Predators at the 2012 trade deadline for a 2nd-round pick, which turned into Jacob De La Rose - who has yet to establish himself as an NHL player. Kostitsyn's NHL career would come to an end after the 2011-12 season. He continues to play in the KHL today.
11 Too Soon: Alexei Kovalev
Alexei Kovalev was traded to the Montreal Canadiens from the New York Rangers in March of 2004. Kovalev played in five seasons for the Habs and was one of their most prolific scorers during his stay. After having one of the worst seasons of his career in 2006-07 scoring 18 goals and 47 points in 73 games, Kovalev sparked controversy after allegedly criticizing his team, coaches and the Montreal media in an interview with a reporter in Russia. During the 2007-08 season, "Kovy" responded with one of the best seasons of his career playing on a line with Tomas Plekanec and Andrei Kostitsyn. He scored 35 goals and 84 points in 82 games. The Russian was even awarded with the team's captaincy on two separate occasions as a replacement for Saku Koivu who dealt with injury.
The Russian forward walked away from the Habs as an unrestricted free agent in July of 2009. We don't know exactly why the two parties couldn't come to an agreement, but Kovalev has admitted that leaving Montreal to sign with the Ottawa Senators was a bad decision. Unfortunately, many fans were left disappointed to see their favourite player and one of the team's best scorers leave so soon.
10 Too Long: Travis Moen
Travis Moen won a Stanley Cup with the Anaheim Ducks in 2007. When the Montreal Canadiens signed him in July of 2009, they were looking to bring in valuable experience to the team on a three-year term. This proved to be a solid deal for the Canadiens as Moen did his job well over the course of the three years, putting up his usual near-20-point seasons and being a decent bottom-six forward.
At the end of his contract, the Canadiens extended the Saskatchewan native to a four-year deal worth an average of $1.8 million per season. At 30 years old, that contract was probably too long for a guy like Moen. He began to lose his impact on the team shortly after. Moen played in two more seasons for the Habs, totalling four goals and was traded in the third year of his contract to the Dallas Stars for Sergei Gonchar. Despite proving his worth when they first brought him in, the Canadiens should have approached Moen's extension differently. Replacing him with a younger body would have been a wiser decision, as it's rare to see a fourth line player be kept around for seven years.
9 Too Soon: John LeClair
The Montreal Canadiens have made some terrible trades in the past that have backfired on them. Trading John LeClair to the Philadelphia Flyers in 1995 was one of them. The Canadiens drafted him in the second round of the 1987 entry draft. LeClair played in 224 games over the course of five seasons for the Canadiens, scoring 118 points.
With the Habs desperate to save a difficult 1994-95 season, LeClair was packaged in a deal that sent himself along with Gilbert Dionne and Eric Desjardins to the Flyers for Marc Recchi and a third round pick (Martin Hohenberger). This was a trade that general manager Serge Savard would instantly regret. LeClair found chemistry with Hall of Famer Eric Lindros and became a dominant 50-goal-scorer. He posted a career-high 51 goals and 97 points in 1995-96, just one season after being traded. The native of Vermont would go on to have an extraordinary career and finish with a total of of 819 points in 967 games.
8 Too Long: Rene Bourque
Rene Bourque was signed as an undrafted player by the Chicago Blackhawks in 2004. After making his NHL debut in 2005-06, Bourque was traded to the Flames in July of 2008, before he'd eventually be dealt to the Montreal Canadiens in January of 2012.
Bourque scored 5 goals and was a minus-16 in the 38 games he played with Montreal to finish off the 2011-12 season. Injuries became an issue for the undrafted forward as he missed the start of the next season due to an injury suffered in the summer. Bourque would spend three more seasons with the Canadiens, playing in a total of 103 games. He recorded 16 goals during that time and was eventually traded to the Anaheim Ducks for Bryan Allen in November of 2014. It's understandable that Bourque's contract made it hard for the Habs to get rid of him. Nonetheless, Bourque's stay in Montreal was difficult to watch considering the Habs gave away Mike Cammalleri, who went on to have a couple more 20-plus goal seasons.
7 Too Soon: Ryan McDonagh
Ryan McDonagh was drafted 12th overall by the Montreal Canadiens in the 2007 NHL draft. While still playing for the University of Wisconsin in the WCHA, McDonagh's rights were traded by the Canadiens to the New York Rangers in June of 2009 in a huge deal that included bringing Scott Gomez to Montreal.
That trade was won by Montreal for maybe one season. As many Habs fans recall, Scott Gomez went on to struggle severely to find the back of the net, and Ryan McDonagh is currently the top defenseman on the Rangers, as well as their captain. He's put up consistent 30-40 point seasons in the past four seasons and hasn't been lower than a plus-11 in his career. This trade executed by former Habs GM Bob Gainey is surely one of the worst in Canadiens history and one that the club's fans will never forget.
6 Too Long: Steve Begin
The Montreal Canadiens claimed Begin off waivers from the Buffalo Sabres in October of 2003. He was nowhere near a top scoring forward and was more of a bottom-six energy guy, so his stats aren't the flashiest. The French-Canadian spent five seasons with the Bleu, Blanc et Rouge and only had one good season statistically where he put up a career-high 23 points in 76 games in 2005-06.
Throughout his tenure with the Habs, Begin suffered a few injuries which kept him out of the lineup for long periods of time. Besides the 2005-06 season, he never appeared in more than 52 regular season games for Montreal. It was evident that these injuries hindered his play, and was no longer able to be the same type of energy player as in previous seasons. It was only until February of 2009 that the Canadiens decided to part ways with Begin by trading him to the Dallas Stars for Doug Janik. In this situation, it would have been wiser for the Habs to replace the Quebec native with a younger and healthier player much earlier.
5 Too Soon: Chris Chelios
When the Montreal Canadiens drafted Chris Chelios in the second round of the 1981 draft, they found a diamond in the rough, drafting one of the greatest defensemen in history. The first seven seasons of Chelios' Hall of Fame career were spent in Montreal. He put up 64 points in 74 games in his first full season as a Hab.
The Chelios trade is still a head scratcher to many Canadiens fans. Many feel like the reason he was shipped out was because of what happened two days prior to the trade. The native of Illinois had been accused of fighting with two police officers who were arresting him for urinating in public outside of a bar in Wisconsin. If this was the reason, then the Canadiens organization shouldn't have such a tight leash as they ended up trading an All-Time great for Denis Savard. Chelios scored 948 points in his 1600-plus-game career, and retired at 48-years-old in August of 2010.
4 Too Long: Jason Ward
The Montreal Canadiens selected forward Jason Ward eleventh overall in the 1997 draft. Ward impressed putting up 64 points in 58 games for the Eerie Otters in his draft year, but was never able to become a forward of first-round value like the Canadiens had hoped.
Ward played in six seasons for the franchise, but spent most of his time in the AHL. Six seasons was far too long for the Habs to keep this guy around, as it quickly became clear that Ward was a draft bust. However, the club never bothered to trade him to get whatever they could in return. The Ontario native appeared in 105 games for the Habs and scored just 10 goals. The Canadiens didn't re-sign Ward to a new contract at the end of the 2004-05 lockout season, and he would go on to sign with the New York Rangers that summer.
3 Too Soon: P.K. Subban
A trade that is still fresh in the minds of Habs fans is the P.K. Subban for Shea Weber blockbuster deal that went down in June of 2016. This trade had the city in an uproar for quite some time with fans sharing their subjective views on the trade. However, after all that Subban has done for the Children's Hospital in Montreal, many were upset at the management for dealing him a year after pledging $10 million over seven years to the hospital.
There's no question that the Canadiens lose this trade in terms of age. The 32-year-old Weber is four years older than Subban who has entered the prime of his career. At the moment, the Habs are in desperate need of puck-moving defensemen and they gave up their best one in Subban a year ago. It's no secret that Subban's time in Montreal came to an end too soon. With his love for the city, the fans, and the team, it seemed like the former Norris Trophy winner would be wearing the Habs sweater for his entire career.
2 Too Long: Kyle Chipchura
Kyle Chipchura is another one of the biggest draft mistakes made by the Montreal Canadiens. Drafted 18th overall in 2004, Chipchura played in five seasons for the organization, but spent most of his time in the AHL with the Hamilton Bulldogs.
Chipchura was never capable of playing more than 39 games in an NHL season before the Canadiens traded him to the Anaheim Ducks in December of 2009. He scored just 4 goals in 68 games for the team. Despite seeing very little action for the Canadiens, it was clear that there was no hope for Chipchura in Montreal. There were much better options for them in the 2004 draft and the former Prince Albert Raider should have never been considered. The 31-year-old didn't do much in the rest of his NHL career and currently plays for HC Kunlun Red Star of the KHL.
1 Too Soon: Patrick Roy
Patrick Roy being traded from Montreal remains as the most popular trade in Montreal Canadiens history. Even though the Hall of Fame goaltender spent twelve seasons with the organization that drafted him in 1984, some might say that Roy left too soon. This should come at the blame of former coach Mario Tremblay, who presumably had a tense relationship with the four-time Stanley Cup Champion and ultimately caused the trade. After being embarrassed in an 11-1 loss to the Detroit Red Wings, Roy went up to the former head coach saying it was his last game in Montreal.
The Quebec native went on to win two more Stanley Cups with the Colorado Avalanche and went down as one of the greatest goaltenders of all-time. He holds records for the most NHL playoff games played by a goaltender (247), most playoff wins (151), first NHL goaltender to play in 1,000 games, first goaltender to 500 wins, and has the most Conn Smythe trophy wins with three.