The Montreal Canadiens are historically one of, if the not the greatest team in NHL history. You don't win a record 24 Stanley Cups without acquiring some talented players. Whether it was through the draft, trades, or the signing of free agents, the Canadiens have made many great acquisitions throughout the years.
However, with the Canadiens long and storied history, it's impossible for them not to have made some bad acquisitions along the way. When it comes to drafting players, they have drafted more than their fair share of players who turned out to be gigantic busts. They also acquired certain players who they hoped would take the team to the next level, but instead these players only saw their careers die in a Habs jersey. The team has also thrown big money at free agents, only to have to buyout the player a couple seasons later.
Here are 15 of some of the worst acquisitions in Montreal Canadiens history, and what the players they regret acquiring are up to today.
16 Sergei Samsonov
Sergei Samsonov was coming off one of best seasons of his career when he signed a two-year contract with Canadiens. He was just fresh off helping the underdog Edmonton Oilers make it to the Stanley Cup finals by recording 15 points in 24 playoff games. Samsonov must have used all his offense up with Oilers as he had his worst season of his career in Montreal. He produced a career low 26 points in 63 games with Canadiens.
Samsonov was traded to Chicago where he was even worse production wise. He would, fortunately, resurrect his career with Carolina before finishing off his career with Florida in 2011. Today, Samsonov keeps busy as a scout for the Carolina Hurricanes.
15 Jiri Sekac
Ahead of the 2014-15 NHL season there arguably wasn't a more sought after European free agent than Jiri Sekac. There were a dozen NHL teams that were very interested in his services. In the end, Sekac felt Montreal would be a great fit and inked a two-year entry-level contract with the team. The Canadiens were hoping Sekac could one day develop into a top six forward.
Sekac's time in a Canadiens uniform would last just fifty games. He played mostly a defensive role with Montreal and recorded just 16 points. After failing to produce much for his new team in Anaheim, Sekac had brief stints with Chicago and Arizona. This past season Sekac returned to the KHL and actually put up some decent numbers. Sekac is still just 24 years old so he might get another NHL shot down the road, but it most likely won't be with the Canadiens.
14 Mike Cammalleri
On July 1, 2009, the Montreal Canadiens signed Mike Cammalleri to a five-year contract worth $30 million. Cammalleri was coming off a career season with the Calgary Flames where he scored 82 points, which included an impressive 39 goals. He was only 27 at the time of the signing and was entering the prime of his career. His run in Montreal would, unfortunately, last just two and a half seasons. Cammalleri put up respectable numbers, but he had trouble staying healthy, missing 32 games during his two full seasons with the Canadiens.
During the 2011-12 season, Cammalleri was unhappy in Montreal. He was particularly upset about the lack of playing time he was getting. Just a few days after his public outburst he was traded to the Calgary Flames. After a couple of productive seasons with the Flames, Cammalleri signed a five-year contract with New Jersey in 2014. While Cammalleri isn't getting any younger he still remains a productive player when he's healthy.
13 Alexander Semin
Even though the Canadiens signing of Alexander Semin was a low risk, high reward signing, he still earns a spot on this list. Montreal signed Semin to a one-year contract worth $1.1 million. They were hoping he would find the scoring touch he showed just a couple seasons prior with the Carolina Hurricanes. Semin's tenure with the Canadiens lasted just 15 games where he recorded a measly four points.
Semin would go unclaimed after being put on waivers by Montreal. However, he refused to report to the AHL and thus his contract was terminated by the NHL. Semin headed back home to play in the KHL. While he has put up some decent numbers the last two seasons with Metallurg Magnitogorsk, he is just too much of a headache to ever get another chance in the NHL.
12 David Fischer
The Canadiens were looking to bolster their defensive prospect pool when they selected David Fischer with 20th overall pick in the 2006 draft. The defenseman showed a lot of promise as he had just been named Mr.Hockey, an award given to Minnesota's top high school player. Fischer's next move would be the transition to the University of Minnesota. It ended up being a terrible decision for him as he had trouble transitioning his game. He spent four years in university and showed little of what made him such a tantalizing prospect in the first place.
After the Canadiens failed to offer him a contract in 2010, Fischer was invited to the Vancouver Canuck's training camp. He failed to impress the Canucks brass and would instead spend the next couple of seasons in the ECHL. After playing in the top German league for a few seasons, Fischer played last season in Austria.
11 Brent Bilodeau
After being taken with 17th overall pick in 1991, Brent Bilodeau would have a fairly lengthy hockey career. It's just unfortunate for the Canadiens and Bilodeau that his career did not include playing in a single NHL game. The defenseman put up some impressive numbers in junior, but his offense completely dried up when he turned pro.
Bilodeau finally started showing some offense later in his career when he played for ECHL's Johnstown Chiefs. However, at that point, it was far too late for him to salvage his career. Almost immediately after retiring, Bilodeau took up coaching. He coached in the ECHL, CHL, and was he most recently behind the bench of the WHL's Tri-City Americans. Bilodeau currently lives in Las Vegas with his wife, former WNBA player Cass Bauer.
10 Janne Niinimaa
Janne Niinimaa throughout the years proved that he can be a more than capable offensive defenseman. However, when the Montreal acquired him in 2006, Niinimaa had already shown signs of regression for a few seasons. In order to get Niinimaa from Dallas, they also traded away of the offensively gifted Mike Ribeiro.
In the end, Niinimaa played just 41 games for the Canadiens, registering a paltry three assists. Montreal would be the last stop in Niinimaa's NHL career as he headed off Europe in 2007. After playing in both Sweden and Switzerland, he hung up his skates in 2013. Today, Niinima works as a color commentator for Finnish hockey games. He has also made numerous appearances and Finnish reality television shows.
9 Jason Ward
The first round of the 1997 NHL Entry Draft was loaded with future NHL stars like Joe Thornton, Roberto Luongo, and Marian Hossa, just to name a few. One pick before Hossa was taken the Canadiens took the Erie Otter's Jason Ward with the 11th overall selection. While Hossa has gone on to record over 1100 points in his NHL career, Ward didn't even break the 100-point plateau in his career.
Ward stayed in the Canadiens organization until the 2004-05 season but spent the majority of his time in the minors. Ward joined the New York Rangers in 2005 and actually found a permanent role in the NHL. However, he was nothing more than a grinder in the NHL. After retiring in 2011, Ward became an assistant coach for the OHL's Brampton Battalion. Today, Ward currently works for a sports marketing company in Toronto.
8 Marcel Hossa
Marcel is the younger brother of Marian Hossa. If Marcel ended up being half as productive as Marian, it would be considered a win for Montreal. However, the 16th overall pick in the 2000 draft didn't have much of an NHL career. While he was a great offensive player for Montreal AHL's affiliate when he got the chance to play with the big club his offense was almost non-existent.
In 2005, the Canadiens traded Hossa to the New York Rangers where he would have the best seasons of his NHL career. There was actually a stretch in time where Hossa looked like he might live up to his potential. Playing on the Rangers top line, he scored eight goals in ten games. However, an injury halted his NHL career and he would take off to Europe in 2008. Hossa played last season for Trencin Dukla of the Slovak league.
7 Tomas Kaberle
After playing 13 excellent seasons for the Toronto Maple Leafs, Tomas Kaberle would be shipped off to the Boston Bruins in 2011. While Kaberle would win the Stanley Cup with the Bruins that year, his career fell apart after that point. After a miserable half-season in Carolina, the Canadiens acquired Kaberle in a trade. While Kaberle looked like his old self in his first season as a Hab, he would be bought out by the team less than a year later.
Prior to the 2014-15 season, Kaberle got one last chance to resurrect his career with the New Jersey Devils. However, Kaberle didn't make it out of training camp before he was released. After sitting out of hockey for a year, he played one final season of pro hockey in 2015-16 for Brno Kometa of the Czech league. Today, Kaberle still laces his skates for games of shinny in his new adopted home of downtown Toronto.
6 Eric Chouinard
The Canadiens had every right to be excited about Eric Chouinard's NHL future. The 16th overall pick in the 1998 NHL Draft had back to back 50-plus goal seasons in the QMJHL prior to turning pro in 2000. Chouinard would actually get into 13 games with Montreal during his rookie season. Unfortunately, those would be the only games he would play as a Canadien.
After being stuck in the minors for a couple of seasons, Montreal traded Chouinard to the Flyers in 2003. His eight points in 28 games with the Flyers in 2002-03 would be the best statistical season of his NHL career. Chouinard would also have a cup of tea with the Minnesota Wild before heading off to Europe in 2006. While he never found a place in the NHL, Chouinard has found his calling card in Europe. He's played the past three seasons in France's top men's league.
5 Louis Leblanc
Louis Leblanc had it tough in Montreal right from the get go. The fans were overjoyed when the Canadiens took Leblanc with the 18th overall pick in the 2009 draft. While fans were happy with the skills he brought to the table, the fact that he was a Quebec native only made the hype greater. After spending a year at the prestigious Harvard University and one season in the QMJHL, Leblanc turned pro ahead of the 2011-12 season.
After producing some decent numbers in the AHL, Leblanc earned a call-up with the Canadiens during his rookie season. He would play 42 games with the team while recording ten points. Unfortunately, that is about all the success the Leblanc would have in the NHL. After a couple of uninspiring seasons in the minors, the Habs shipped him off to the Ducks for basically a bag of pucks. Just a couple years later Leblanc announced his retirement and went back to finish his studies at Harvard University.
3 Sylvain Turgeon
There is no denying that Sylvain Turgeon had a few excellent seasons in the NHL. However, his time in a Canadiens jersey was anything but great. Montreal acquired Turgeon in 1990 in exchange for Claude Lemieux. Turgeon was coming off a 30 goal season for New Jersey, which was his fourth 30-plus goal campaign of his career.
The Canadiens were hoping Turgeon would bring his goal scoring pedigree to the team. Instead, all he brought was his injury prone body and inconsistent play. Turgeon was claimed by Ottawa in the 1992 expansion and after a few seasons there he headed off to Europe to finish his career. Today Turgeon lives in Calgary where he works in the home building industry.
2 Scott Gomez
In 2007, Scott Gomez signed a massive seven-year, $51.5 contract with the New York Rangers. While Gomez wasn't a complete bust in New York, his amount of production was definitely not worth the money they were paying him. Despite this fact, the Montreal Canadiens took Gomez' contract off the Rangers hand in a 2009 trade. Not only did the Canadiens trade away future stud defenseman Ryan McDonagh, Gomez was a huge bust in Montreal.
While Gomez' first season with the Canadiens wasn't too bad, he only managed to record a measly 11 points in 38 games during the 2011-12 season. In January of 2013, the Canadiens had enough of Gomez and bought the remaining years of his contract. After Montreal, Gomez' NHL career never really recovered. While he had a bounce back year with the New Jersey Devils in 2014-15, he would announce his retirement just a year later. Gomez was just recently named an assistant coach for the New York Islanders.
1 Terry Ryan
Terry Ryan is one of the biggest draft busts in Montreal Canadiens history. The eighth overall selection in the 1995 NHL Draft, was Montreal's highest selection since they took Petr Svoboda in 5th overall in 1984. Ryan's stay in the organization lasted just three seasons where he found himself playing mostly in the minors. He only managed to get into eight games for the Canadiens before the team cut bait with him in 1999.
Ryan would never get back to the NHL and would instead play the rest of his career in the minors. After playing all the way down in the ECHL in 2002-03, Ryan decided to hang up his skates. While his hockey career didn't pan out, Ryan has found a bunch of new things to keep him occupied these days. He has had bit roles as an actor on Canadian television, he's an author, and he's even tried his hand at being a stand-up comedian.