5 Young Players the Canadiens Gave Up On Too Soon

The Montreal Canadiens have won the most Stanley Cups in National Hockey League (NHL) history. They have produced some of the greatest dynasties in the history of the sport, won well over a hundred individual awards and have seen dozens of their former players inducted into the Hockey Hall of Fame.

There is not another team in the NHL that can compete with the winning history that the Canadiens boast. However, that does not mean the team is without its blemishes. With the benefit of hindsight, the Canadiens have come out on the losing end of many transactions over the years.

One issue NHL teams consistently run into is they lose patience with young players too soon. Some players just do not develop as quickly as others and teams can move on from them before the player really has a chance to prove himself. The Canadiens have fallen victim to abruptly moving on from a player that has not worn their sweater for long, or at all in some cases.

Here are five players the Canadiens gave up on before they even gave the player a chance to show what they could do on the ice.

Danny Grant

It is difficult to question any decisions made by the Canadiens regarding their roster in the 1970s. They won six Stanley Cups in the decade, but could it have been ever better? Danny Grant from Fredericton, New Brunswick was a member of the team, playing just one game in the 1965-66 season and another 22 contests in 1967-68. Then, he was shipped to the Minnesota North Stars, along with Claude Larose for a first-round draft pick in 1972.

In his first season with the North Stars, Grant scored 34 goals and 65 points in 75 games. He would go on to have a total of six seasons in which he scored at least 29 goals and 57 points. His best season came in 1974-75 when he scored 50 goals and 87 points. The Canadiens lost to the Buffalo Sabres in six games in the third round in the 1975 postseason, with three of those contests being one-goal affairs. Could Grant have helped push them over the top that season, and change history by having the Canadiens close the decade with five straight Stanley Cups?

It is impossible to know how it all would have played out. The return for the Habs in the trade was one draft pick that became Dave Gardner. He would play just 36 games with the Canadiens, scoring two goals, before he was then moved for a future first-round draft pick. It is definitely safe to say the Canadiens would have benefited from giving Danny Grant a longer audition than 23 games before moving on.

Mikhail Sergachev

The Canadiens drafted Mikhail Sergachev with the 9th overall selection in the 2016 Draft. They had an aging Andrei Markov and Alexei Emelin on the roster at the time. Nathan Beaulieu was also showing signs he was not going to develop the way the team had hoped, leaving quite a void on left defense, and Sergachev looked like the perfect fit to fill it.

Sergachev played four games with the Canadiens at the beginning of the 2016-17 season but ultimately was sent back to the Ontario Hockey League (OHL) for more seasoning. He performed admirably there and appeared on the cusp of joining the Habs for a lengthy NHL career. However, he was shockingly traded in June, 2017 to the Tampa Bay Lightning for Jonathan Drouin.

Sergachev almost immediately made the Canadiens regret moving him as he scored nine goals and 40 points as a rookie in the 2017-18 season. Meanwhile, Drouin had 46 points as a first line forward that same season. Sergachev continues to be an exceptional two-way defenseman, topping out at 64 points in the 2022-23 season and has won two Stanley Cups with the Lightning. Giving Sergachev more than four games to prove himself, would have quickly convinced the Canadiens they need to keep players like him around.

Tomas Vokoun

Looking back at Canadiens rosters, it seems they had dominant goaltenders for much of their history. There was one significant lull, and that came after they traded Patrick Roy. Jose Theodore had one fantastic season, but goaltending was a problem for many of the years between Roy’s exit and Carey Price’s arrival.

A nice bridge between those two legendary goalies could have been Tomas Vokoun. He was drafted by the Canadiens in the 9th round of the 1994 Draft. He suited up for just one game with the Canadiens, actually playing just one period, and allowed four goals in those 20 minutes of action. He was then claimed by the Nashville Predators in the 1998 expansion draft. The Canadiens chose to protect Jocelyn Thibault instead, as he was their starting goaltender at the time while Vokoun was playing in the American Hockey League (AHL). However, the Canadiens traded Thibault just ten games into the following season.

Had they hung on to Vokoun instead, he would have quickly turned into their starting goalie to close out the 20th century. The Canadiens did get some great goaltending performances around that time from Jose Theodore in 2001-02 as well as a couple of impressive seasons from Cristobal Huet in 2005-06 and 2006-07, which softened the blow of losing Vokoun. However, he would have been a great partner for each of them, as well as a safety net for Price as he began his own NHL career. The Canadiens might have seen that had they kept Vokoun on the roster for more than one period of play.

Ryan McDonagh

Ryan McDonagh was selected with the 12th-overall pick in the 2007 Draft, the same draft that saw the Canadiens take Max Pacioretty and P.K. Subban. It should have set them up to be great for a long time, but they just were not patient enough to really see what they had.

McDonagh was traded to the New York Rangers two years later, before he had even left college, in what is now known as one of the worst trades in Canadiens history. McDonagh was shipped out with Chris Higgins, Pavel Valentenko and Doug Janik for Scott Gomez, Tom Pyatt and Michael Busto. Since the trade 17 years ago, McDonagh has played 16 terrific NHL seasons as a shutdown left defenseman. He was on some great Rangers teams before being traded to the Lightning and helping them win two Stanley Cups. He has played over 1000 regular season games, more than 200 playoff contests and has been to the Stanley Cup Final four times in his great career.

Had the Canadiens been less hasty when it came to McDonagh’s career, he could have been a perfect partner for Subban for many years, or an exceptional second pairing defender behind Markov and Subban, making the Canadiens blue line a force. It was not to be, as the Canadiens never gave McDonagh a single game to show them what he could do.

Ted Kennedy

Ted Kennedy was one of the best Toronto Maple Leafs players of all time. However, he was initially property of the Montreal Canadiens. The Port Colborne, Ontario native was signed by the Canadiens, but grew homesick after attending their training camp when he was just 16 years old. The Canadiens relented, and traded the youngster to the Maple Leafs for Frank Eddols who would play 57 career games with the Habs before moving on to the Rangers.

Kennedy would blossom as the leader of the Maple Leafs in the 1940s and won five Stanley Cups in a seven season span between 1944 and 1951. Kennedy won the Hart Trophy and the league’s most valuable player in 1955, which would be his last full season in the NHL. He was known as a sparkplug type player who would grind and outwork his opponent on every shift, while being one of the top scorers of his era. Kennedy was enshrined in the Hockey Hall of Fame in 1966 and was named one of the NHL’s Top 100 players by the league in 2017.

Meanwhile, the Canadiens lost in Game 7 of the Stanley Cup Final in 1954 and 1955. They also lost in the Stanley Cup Final to Kennedy’s Maple Leafs in 1951 and 1947. You can not replay history, but it stands to reason the Canadiens would have hung a few more banners in the rafters during those years. All they had to do was be a little more patient with a teenager who was unsettled when he first moved miles from home, and Kennedy’s Hall-of-Fame career could have occurred in Montreal.