July 1st is perhaps the most exciting day in the NHL. Trade Deadline day used to hold that title but with the salary cap restricting movement and the majority of teams believing they have a shot at winning, the moves have gotten less exciting each year.

But the salary cap holds no power on July 1st. Every team believes they can move forward with the right signings and the hungry teams far outnumber the talented players. Lower-end players from championship teams are signed for big money as teams hope to bring in the right ingredients to their locker room.

But if players wait too long those rosters fill up and the salary cap starts looming its ugly head once again. Last season regulars wind up the next season’s tryouts.

Compared to other big market teams, Montreal has a stellar record when it comes to free agents. They rarely throw big contracts around, have a habit of extending players rather than competing for their services, and are extremely quick to ship a player out if it’s not working.

Because of their tendencies, this was a hard list to build and many players mentioned here wouldn’t have caused a blip on another team’s UFA low-lights. Considering $1.1 million for Semin a failure is minor compared to how much Carolina paid him to go away.

If you’re a Montreal fan, soak it in. It’s rare that a team shines in a “Worst” list. Although the franchise hasn’t come close to the Stanley Cup exploits of decades past they still appear to be run fairly well (ignoring Ryan McDonagh for Scott Gomez of course).

So let’s take take a look at the “worst” free agent signings in Montreal Canadiens history.

12. Andrei Markov

Eric Bolte-USA TODAY Sports

Eric Bolte-USA TODAY Sports

Andrei Markov has been a loyal soldier for the Canadiens, having spent 15 years in Montreal. When it came time for Markov to see if he could test free agency after the 2013-14 season, he again re-upped with the Habs. It seems now though that the Habs overestimated Markov’s shelf life, handing him a three year deal at $5.75 million a year. Markov has slowed down considerably in 2015-16 and was even showing signs of decline in last year’s playoffs. The Habs are now down in the dumps and would probably love to use that cap money elsewhere.

11. David Desharnais

Jean-Yves Ahern-USA TODAY Sports

Jean-Yves Ahern-USA TODAY Sports

Many have pointed to this contract as Marc Bergevin’s first mistake as Canadiens GM. With Desharnais having a good year in the lockout shortened season of 2012-13 and coming off a good season playing alongside Max Pacioretty and Erik Cole, Desharnais was signed to a four-year, $14 million deal. While Desharnais tends to hover around 50 points when all is said and done every season, he often goes through prolonged stretches without points and has often been slotted as the Habs’ no.1 centre, a role for which he seems miscast.

10. Sergei Samsonov

via bleacherreport.com

via bleacherreport.com

The Habs have a history of signing undersized but highly skilled forwards, and Samsonov fit that bill perfectly. With five seasons of 20 or more goals, Montreal signed Samsonov to a two-year deal worth $7.05 million in 2006.

He was largely a disappointment. Age and his size caught up with him as he struggled to produce, even spending a few games as a healthy scratch and was even placed on waivers. He finished with just nine goals in 63 games.

That was all Montreal needed to see and they moved him to Chicago in the off-season.

9. Georges Laraque

via sportsnet.ca

via sportsnet.ca

Tired of being pushed around, Montreal gave the feared enforcer a three year deal worth $4.5 million in 2008. It was a large amount of money considering his role, but his name carried considerable weight around the league at the time.

They wouldn’t get much for their money unfortunately as Laraque struggled with back injuries for the first two years of the deal, prompting the franchise to buy out the third year of the deal. Laraque contributed just one goal, four assists, and 87 penalty minutes in 51 games with the club.

8. Jaroslav Spacek

via nhl.com

via nhl.com

The oft-traded Spacek hit the 45-point mark for just the second time in his career before signing with Montreal for $11 million over three years.

It wasn’t exactly a success with just 21 and 16 points over his first two Montreal campaigns. He would be traded to Carolina after just 12 games and more injuries.

This was a tumultuous time for the Habs, with poor communication from management and players confused about their role. Spacek told the Canadian National Post “So much bad stuff. In my 20-year hockey career, I’d never seen anything like it. If you don’t like the way I play, kick me in the ass. But no one said anything, it was terrible”.

In a better situation, Spacek might have offered leadership and dependable lower pairing minutes. It may not be his fault, but he still winds up on our list.

7. Mike Cammalleri

via nhl.com

via nhl.com

After scoring 39 goals and 82 points for Calgary in 2008-09, Montreal signed Mike Cammalleri to a lucrative five-year deal worth $30 million.

Although he tied a franchise record for goals in a playoff series against Pittsburgh, his time in Montreal was below expectations due to frequent injury problems. In three seasons with Montreal he would only play 65, 67, and 38 games.

Montreal eventually traded him back to Calgary for the rest of the 2011-12 season.

6. Daniel Briere

Jean-Yves Ahern-USA TODAY Sports

Jean-Yves Ahern-USA TODAY Sports

When Daniel Briere finally got a chance to play for his hometown Habs it seemed like the perfect fit.

Montreal usually favored skill over size and the little wonder had a sparkling point-per-game average in postseason play. Canadiens fans were excited to see if he could get them over the playoff hump.

But it never quite panned out. Like many of these stories, a serious injury (concussion) occurred and Briere found himself playing some of the lowest minutes of his career courtesy of head coach Michel Therrien. In more than half of the playoff games he played less than eight minutes!

Although he didn’t get a chance to light up the score sheet he still left a positive impact on several teammates. Lars Eller tweeted “..was a big fan of his before, and even bigger one after I had the privilege to play with him. Great person and role model”

5. Tom Gilbert

Russell LaBounty-USA TODAY Sports

Russell LaBounty-USA TODAY Sports

Tom Gilbert has been a solid puck-moving defenseman for most of his career, but he’s rarely looked comfortable while wearing Montreal’s bleu, blanc and rouge.

Expected to pick up the slack last season for the departing Josh Gorges, Douglas Murray and Francis Bouillon, Gilbert has instead spent most of his time on the bottom pairing, behind right-handers P.K. Subban and Jeff Petry. Heck, even Sergei Gonchar was getting more minutes than him last year.

This season has been even worse, with Gilbert sitting at a measly one assist in 36 games of this writing. The $2.8 million cap hit isn’t a big loss but Montreal must still be disappointed with what they’ve seen so far.

4. Alexei Emelin

Kim Klement-USA TODAY Sports

Kim Klement-USA TODAY Sports

Alexei Emelin was a third-round pick of the Habs in 2004 but didn’t make his way to the club until 2011, signing a one-year, two way contract with the team. He brought some physical play, as he seemed to be the only defender capable of delivering bodychecks in the Habs’ last place season of 2011-12. He signed a short-term extension after that season.

Emelin impressed the Habs enough in the lockout shortened season of 2012-13 to warrant a four-year extension worth $4.1 million per season, locking him up before he would have become a UFA. Emelin was injured at the time of the signing but the Canadiens were confident he would remain a core part of their defensive core for years to come.

Although he scored 12 points in 38 games before the signing, he has yet to crack the 20-point barrier in two seasons since. He’s shown flashes of great play but also plenty of inconsistency. Shuffling around the pairings and constantly playing his off-side hasn’t helped matters.

If Emelin can put it together and progress into a reliable top-four defender this contract will make sense, but as of now it’s a drain on cap space.

3. Jiri Sekac

James Guillory-USA TODAY Sports

James Guillory-USA TODAY Sports

Undrafted, Sekac made a name for himself in the KHL before Montreal signed him July 1, 2014. Sekac himself said “It just didn’t work in Montreal..”

“It was hard. I was playing as a defensive forward. I was out there playing on defensive face-offs and it doesn’t seem like it, but that sucks a lot of energy out of you and you have nothing left for offense.”

After just 50 games and 16 points Montreal had seen enough and swapped him to Anaheim for Devante Smith-Pelly. Anaheim only gave him 41 games before trading him to Chicago for Ryan Garbutt, where Sekac has already been a healthy scratch.

Montreal once again proved they move on quick from potential free agent busts.

2. Alex Semin

Jean-Yves Ahern-USA TODAY Sports

Jean-Yves Ahern-USA TODAY Sports

When Montreal signed Semin for $1.1 million many believed it was the bargain of the summer. Surely the former 40-goal man would use this opportunity to bounce back and cash in the following season.

Unfortunately 2015-16 was another disaster and he was demoted to the minors after clearing waivers. Whether the team was a bad fit, age had caught up, or he’s lost all passion to play in the NHL, it appears to be the end of the road for Semin.

1. Manny Malholtra

Jean-Yves Ahern-USA TODAY Sports

Jean-Yves Ahern-USA TODAY Sports

Being a top-10 draft pick can put giant expectations on a young player that follows them throughout their career. The Rangers GM and coach at the time disagreed about his potential. With GM Smith regarding Malholtra so highly that he refused to include him in a trade for Vancouver’s Pavel Bure, and Coach John Muckler declaring he would never be more than a bottom six forward. Turns out Muckler was right.

Although Malhotra was one of the best faceoff men in NHL history and at times very useful defensively, by the time he got to Montreal he was largely ineffective after the puck drop.

He scored a single goal and three assists for the franchise in 58 games as Torrey Mitchell effectively replaced him as fourth-line center.

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