Five Best Montreal Canadiens Trade Deadline Deals Ever

The Montreal Canadiens head into the trade deadline as sellers and will look to add some future assets to the organization in the coming days.

Time is running low as the deadline hits on Friday afternoon and teams only have three more days to fill out their roster before a playoff push. The Canadiens have already started selling as they traded Sean Monahan for a first round pick, and will look to make a few more moves to keep rebuilding.

We have seen the Canadiens make terrific deals at this time of year in previous seasons. Whether they were buyers or sellers at the time, the Canadiens have taken advantage of their position in the standings and either added an impact player to help them in the postseason, or shipped out veterans who they didn't really need anymore and landed huge parts of their future.

There has always been a "trade deadline" but teams really didn't go out shopping this late in the season back in the day. Of course, the Canadiens were winning Stanley Cup titles every other year back then so they didn't really have to go out and add anything.

For example, when the Canadiens won the Stanley Cup in 1993. the only players they acquired during the season were Gary Leeman and Rob Ramage. They had strong seasons at different points in their careers, but Leeman had just one goal and three points in 11 playoff games and Ramage was held scoreless in seven postseason contests that spring.

So, havind said all that, many of these trades happened in more recent years.

While we wait and hope general manager Kent Hughes can pull off a major deadline deal that allows this team to become a contender in the next couple of years, we can look back at the best trades this team has ever made at the trade deadline.

Let's count down the five best trade deadline deals made by the Montreal Canadiens.

5. The Brett Kulak Trade

Brett Kulak was a bit of a gift for the Montreal Canadiens who got him for basically nothing, and were able to squeeze some pretty good hockey out of the left defenseman. He cleared waivers twice in 2018 and was then traded to the Canadiens for Matt Taormina and Rinat Valiev.

Kulak turned into a reliable two-way defender who always had impressive advanced stats and was a borderline second pairing defenseman for a couple years in Montreal. He helped the Canadiens reach the Stanley Cup Final in 2021, but was a pending free agent the following season, and the Canadiens were not going back to the playoffs.

So, in March of 2022, Kulak was shipped to the Edmonton Oilers for a second round draft pick in 2022, a seventh round pick in 2024 and William Lagesson. Lagesson played a couple of games for the Canadiens that season and the seventh round pick isn't likely to amount to much, but getting a second round pick for Kulak was really good value at the time.

Many people were debating ahead of the trade deadline whether or not the Canadiens could get a third or fourth round pick for Kulak so it was surprising to see him go for a second rounder. That makes it a great trade on the day it was pulled off.

However, since the Canadiens now had an extra second round pick, and had already picked twice in the first round, they were able to gamble a little with their extra second round pick. The Canadiens selected Lane Hutson with that pick acquired in the Kulak trade, and he was seen as a super skilled, elite offensive player that was just tiny.

Hutson has since gone to college for two seasons and grown substantially while putting up numbers almost never seen at the NCAA level. He is among the very best prospects in the hockey world, and the Canadiens were able to select him because of a trade deadline deal two years ago.

3. The Craig Rivet Trade

The Montreal Canadiens were in a tough spot in the 2006-07 season, especially as the trade deadline neared. They were not really considered a huge Stanley Cup contender, but they had an elite power play that was carrying them in a season where power plays were plentiful.

They also were getting strong goaltending from Cristobal Huet and it gave them a chance to make the playoffs at least. They had snuck into the postseason the previous season and made life difficult on the Carolina Hurricanes in round one before Saku Koivu was injured and then the Hurricanes went on to win the Stanley Cup.

What made things difficult around the trade deadline was three of the Canadiens best defensemen were all pending unrestricted free agents, but the team was on the cusp of qualifying for the playoffs. They couldn't really trade all of Andrei Markov, Sheldon Souray and Craig Rivet, but they couldn't afford to lose them all for nothing in the offseason either.

With a tight salary cap at that time, there was no way they could afford all three either. So, they elected to trade Rivet to the San Jose Sharks for a first round pick, and Josh Gorges. The Canadiens ended up missing the playoffs by a single point, but the short term pain was outweighed by the long term gain of this deal.

Gorges turned into a top pairing defender for the Canadiens, often playing alongside P.K. Subban and taking on a ton of minutes at even strength and the penalty kill. Also, the first round pick was used to select Max Pacioretty.

Pacioretty was the best goal scorer on the Canadiens for nearly a decade and made the trade a steal of a deal for the Habs. They may have just missed the 2007 playoffs because of this deal, but they would not have made it in 2013, 14, 15 or 17 without Pacioretty leading the team's meagre offense all those years.

2. The Alex Kovalev Trade

The Montreal Canadiens were in a bit of a funk in the late 1990's and it spilled over into the early 2000's as well. The team had some of its worst seasons every around the turn of the century, though a ridiculous Jose Theodore season in 2001-02 saw them make the playoffs (barely) once in a five year span.

They finally snapped out of that drought in 2003-04 and had a lot more success after the 2005 lockout than they did in the years leading up to it. A lot of that success started with the acquisition of Alex Kovalev.

The Canadiens were in a battle for a playoff spot in 2004 but didn't have a ton of scoring. A couple of rookies were leading the way as Mike Ribeiro and Michael Ryder had some early success and they did still have Saku Koivu and Richard Zednik but that was about it for offense. They needed a bit more to round out their top six and they got it at the trade deadline.

The New York Rangers were a high spending but disappointing team that season and had a yard sale at the deadline. Brian Leetch, Martin Rucinsky, Vladimir Malakhov, Petr Nedved, Matthew Barnaby and Greg DeVries were all traded that deadline, along with Kovalev.

The return for Kovalev was Josef Balej and a second round pick. Kovalev would immediately help the Canadiens upset the Boston Bruins in the first round of that year's playoffs, and become they go-to offensive threat for the next four seasons. His 2007-08 season saw him score 35 goals and 84 points, which is the only time a Canadiens player had over 80 points since 1998.

Considering the modest return, getting a game breaking offensive talent like Kovalev at the deadline was an incredible trade for the Canadiens.

1. The Phillip Danault Trade

The Montreal Canadiens had a pretty good showing for a few years when Carey Price really cemented himself as an elite goaltender. Their 2013, 2014 and 2015 seasons were full of more ups and reasons for optimism than anything else. They didn't get over the hump, but had great regular seasons and won three playoff rounds in a short period of time.

Then came the 2015-16 season when they started extremely well, only to have their entire season fall apart because Carey Price stepped on a puck in warm up and was out for basically the rest of the season.

The team crumbled and fell well outside the playoff picture after a strong start which made for a disastrous year when expectations were quite high going in. What it did lead to was some selling at the trade deadline, and that has had a lasting positive impact.

The Canadiens did not have a lot of pending free agents to sell that season, but they packaged their two obvious trade candidates and got a great return. The Canadiens sent both Dale Weise and Tomas Fleischmann to the Chicago Blackhawks for Phillip Danault and a second round pick.

Weise would score zero goals and one assist in 15 regular season games and add one goal in four playoff games for the Blackhawks while Fleischmann had five points in the regular season and none in the playoffs.

That was the end of Fleischmann's career while Weise went on to play a couple more seasons with the Philadelphia Flyers.

Meanwhile, Danault turned into an incredible defensive center who averaged nearly 50 points per 82 games with the Canadiens once he settled into his role with Brendan Gallagher and Tomas Tatar. The draft pick turned into Alexander Romanov who was then essentially moved for Kirby Dach who looks to have a bright future with the Canadiens.

To take a couple of aging wingers like Weise and Fleischmann and turn them into big parts of the team's future was amazing work by Marc Bergevin and remains the best trade deadline deal we have seen the Montreal Canadiens pull off to date.