CW: The following article contains references to sexual assault

Despite the Montreal Canadiens losing the 2021 Stanley Cup Final to the Tampa Bay Lightning, their first run to the Finals since 1993 captured the hearts of Habs fans during a difficult time.

From beating the heavily favoured Toronto Maple Leafs in seven games, to sweeping the Winnipeg Jets and finally dispatching the Vegas Golden Knights on home ice in overtime on Saint-Jean-Baptiste Day, the Habs were the inspiring underdogs this past spring and summer.

However, since their magical run ended on July 7 in Tampa Bay, the Habs did not carry that positive momentum into the off-season.

From making a very controversial draft pick, the departures of key personnel, and injuries, here is a timeline of the major moves that have defined the Habs’ off-season.

June 27 – While this information came out ahead of Game 1 of the final, Canadiens GM Marc Bergevin responds to the 2010 sexual assault allegations against then-Chicago video coach Brad Aldrich that emerged. Bergevin, who was director of player personnel of the Blackhawks that season, releases a statement that he was not aware of the allegations at that time.

"It came out recently. There was a meeting that I heard that was done in Chicago,” said Bergevin. “I was not part of any meeting, and I was not part of any decision based on that.

"And I was not aware of anything going on at the time. So you can go on the record with that."

Investigations into the allegations remain ongoing.

July 9 – Joel Bouchard, head coach of the AHL’s Laval Rocket, departs for the Anaheim Ducks organization, joining their AHL affiliate, the San Diego Gulls as their new head coach.

July 22 – Bergevin announces that captain Shea Weber is unlikely to play next season and that his career is likely over due to injuries. This past season, he dealt with thumb, ankle and knee injuries. The 35-year-old has spent the past five seasons with the Habs after being acquired from the Nashville Predators in exchange for PK Subban.

Bergevin also notes that forward Jonathan Drouin, who took a leave of absence for personal reasons prior to the start of the playoffs, will be at training camp.

July 23 – After being exposed in the Seattle expansion draft, goaltender Carey Price is not selected by the Kraken and undergoes knee surgery in New York. Recording a .924 save percentage and 2.28 goals-against average in the playoffs, it was a strong rebound from a down regular season for Price, which included suffering a concussion towards the end of the season. He is expected to be ready for training camp.

July 23 – The Habs shock the hockey world by drafting London Knights defenceman Logan Mailloux.

The 18-year-old, who spent the 2020-21 season playing in Sweden, was charged and fined by Swedish police in 2020 for taking a photo of himself and a young woman without her consent during an "intimate moment'' and then shared that photo with his teammates "to impress them.''

Prior to the draft, Mailloux stated he did not want to be selected. The Habs drafted him anyways with the 31st overall pick, with fans, corporate sponsors and even Prime Minister Justin Trudeau expressing disappointment in the team’s decision to draft Mailloux.

"We will work closely with him, give him the support that he needs. I know he's been remorseful about the incident, which we truly don't agree with it in all sense of the word,'' Bergevin said. "But he's a young man who made a serious mistake of judgment. And we need to work with him and we did talk to him and he's very aware of that and very remorseful. So that is a big step.''

The team also announced that he would not participate in the team’s rookie and main training camps for the upcoming 2021-22 season.

July 28 – NHL free agency opens with the departure of key personnel.

Centre Phillip Danault, who played an important role as Montreal’s shutdown centre in the playoffs, signs a six-year, $33 million contract with the Los Angeles Kings. Two days later, veteran Corey Perry inks a two-year deal with the Lightning.

The Habs would add forward Mike Hoffman and defenceman David Savard to three- and four-year contracts respectively on the first day of free agency.

July 30 – Assistant captain Paul Byron undergoes hip surgery with full recovery expected to be five months. Byron had five goals and 11 assists in 46 games last season, and three goals and three assists in 22 playoff games.

August 5 – After being scratched throughout the playoffs, Tomas Tatar signs a two-year contract with the New Jersey Devils. Tatar, who arrived in Montreal in 2018 as part of the return in the Max Pacioretty trade with Vegas, had 57 goals and 149 points in 198 regular-season games for the Habs. 

Danault and Tatar, along with current Hab Brendan Gallagher, were consistently one of Montreal’s best lines the last few seasons.

August 28 – Forward Jesperi Kotkaniemi signs a one-year, $6.1 million offer sheet with the Carolina Hurricanes. The 21-year-old had five goals and 15 assists in 56 games last season, including five goals and three assists in 19 playoffs. Kotkaniemi was a healthy scratch three times during the Habs’ playoff run, including the last two games of the Stanley Cup Final.

Drafted third overall by the Habs at the 2018 NHL Draft, Kotkaniemi made the NHL roster as an 18-year-old. He struggled in his second season, which led to an AHL stint. The offer sheet from the Hurricanes comes two years after the Habs offer-sheeted Carolina forward Sebastian Aho, which the Hurricanes matched.

September 2 - Mailloux is suspended indefinitely by the Ontario Hockey League for violating the league's expectation for appropriate conduct by a player. He is eligible to apply for reinstatement on Jan. 1, 2022, where the decision will be made based on his conduct and the appropriate treatment, counselling, mentoring or education he has received.

September 4 – The Habs elect not to match the Hurricanes’ offer sheet to Kotkaniemi and will receive Carolina’s first and third round picks in 2022. Hours later, the Canadiens acquired centre Christian Dvorak from the Arizona Coyotes in exchange for a conditional first-round pick in the 2022 NHL Draft and a second-round pick in the 2024 NHL Draft.