These moves left general managers, fans and even sports bookies confused, as the odds had these teams at the top of their NHL standings predictions; buying into the hype of improvement.

As the Montreal Canadiens gear up for an important here are three major errors that rivals have made that should be avoided if they wish to hit another level in the coming years.

Overspending On Free Agents

Overspending on free agents is a way of life, especially for Canadian teams like the Montreal Canadiens, but it could sometimes come to bite you in a cap crunch.

Just take the Toronto Maple Leafs as an example, signing future Hall of Fame forward Patrick Marleau to a three-year deal worth $6.25M per season in the summer of 2017. Although Marleau’s leadership was seen as extremely valuable, it came with significant risk, as the former 2nd overall pick in the 1997 NHL Draft had just turned 38 by the time he had first played a game for the Leafs.

After two underperforming years, the Maple Leafs were stuck. They needed cap space to sign another free agent in John Tavares, while keeping some flexibility to sign their emerging core of Auston Matthews, William Nylander and Mitch Marner.

The result? They had to pay an unprotected 1st-round pick to the Carolina Hurricanes to take on Marleau’s contract; proving the signing to be a blatant, unforced error by former GM Kyle Dubas.

What’s worse? Carolina used that 1st-round pick to select breakout star Seth Jarvis at 13th overall in the 2020 NHL Draft.

Imagine where the Leafs would be right now with a cost-controlled Jarvis in their lineup?

Habit of Overspending

Montreal Canadiens general manager has mentioned in the past that he’s willing to overpay for players or assets he truly covets.

In the right deal, that could be fine, but, more often than not, it can set back your rebuild quite a bit, especially if the acquired asset isn’t tied down long-term.

At the 2022 NHL Draft, the Ottawa Senators sacrificed the 7th overall pick and 39th overall picks, along with a 2024 3rd-round pick, to acquire star scorer Alex DeBrincat.

The move was made in an effort for the Senators to take the next step in their rebuild to finally begin competing for the playoffs, but that aggressiveness proved to be ill-advised.

Not only did Ottawa make the trade without a commitment from DeBrincat to remain in Ottawa long-term in the form of an extension, but the Senators were forced to trade him a year later after having missed the playoffs yet again, to a divisional rival in the Detroit Red Wings.

The following year, during this past 2022-2023 season, the Senators took a big step back after the loss of DeBrincat and the organizational overhaul that ensued from the failure of the rushed rebuild.

Now the Senators will look to make sweeping changes to a rebuild that most pundits had earmarked as a future powerhouse.

Hold Onto Underperforming Prospects Too Long

This is perhaps the hardest issue to overcome, as NHL prospects are usually

The Montreal Canadiens have been guilty of this in the past, ultimately trading former 1st-round picks like Louis LeBlanc, Michael McCarron and more for pennies on the dollar.

Then there were the Nikita Schebaks, Noah Juulsens and Victor Metes who were also lost to waivers. Some can be viewed as circumstantial, but it’s imperative to extract value with your top picks and prospects for a rebuild to be successful.

The Ottawa Senators are kind of in the same bind, as they spent good assets in the form of 1st-round picks to try and fill their big need on the right side of their defence. Drafting Lassi Thomson (2019) and Jacob Bernard-Docker (2018) and trading for Erik Brannstrom (a leftie who can play on the right side).

All three have failed to establish themselves as the bonafide top-4 defencemen that they were pegged to be in their draft years, with Bernard-Docker just starting to crack the NHL full-time at 23 years old.

The case of Brannstrom was well-known, as he was unhappy in Ottawa based on his usage, after being the key piece acquired in the Mark Stone trade of 2019. Now, with his trade value all but depleted, the Senators are expected to move him for pennies on the dollar, having virtually nothing to show from trading one of the best players to put on the Senators jersey in the last two decades.

In Thomson’s case, he was not only lost to waivers once (before being reacquired by waivers), but has now signed to play in Europe next season. It is a shame, as he did put up good numbers in the AHL as a 20-year-old, but, unfortunately, the Senators waited too long to pull the trigger on trading him for a bonafide solution on defence.

This scrutiny will soon apply to the Montreal Canadiens real soon, as they begin funnelling the 30+ prospects they’ve drafted or acquired by trade into their professional ranks in the coming months.

Highly drafted prospects will be looked to improve, but, with the wealth of depth in their prospect pool, the hope would be that general manager Kent Hughes would pull the trigger on a deal if he feels a prospect won’t live up to the hype; sooner, rather than later.