TheSportster.com

8 Players The Toronto Maple Leafs Should Have Kept And 7 They Never Should Have Chased

When you are an Original Six club, you are bound to have many mistakes in your history. The Toronto Maple Leafs are one of the greatest franchises in the NHL, but it is clear that they have made a handful of atrocious moves. While some did not have long term effects on them, many ended up hurting them in the long run and very well could have hindered them from winning the Stanley Cup. It has been a long time for the Leafs in that department.

In this article, we will be observing eight players who the Maple Leafs should have kept and seven they should have never acquired. This will definitely be an interesting list to look at because the decisions they made on these players turned out to be mistakes that will never be forgotten. If you are a Toronto Maple Leafs fan, we here at TheSportster would like to apologize in advance for reminding you of these terrible decisions.

Nonetheless, here are eight players the Leafs should have kept and seven that they should have never chased.

advertising

15 Kept: Jiri Tlusty

Ed Mulholland-USA TODAY Sports

Although Jiri Tlusty is currently out of the NHL, he was once a very solid player. Back in 2006, the Maple Leafs drafted Tlusty 13thoverall because he was expected to become a dominant playmaker. Yet, his stint with the MapleLeafswas cut short and was he was quickly traded to the Carolina Hurricanes four years later.

For a former first round pick, the Maple Leaf sonly received Phillipe Paradis. Paradis would never play a game for the MapleLeafs, while Tlustygrew into a top player for the Hurricanes. His best season came in 2012-13when he registered 38 points in 48 games in the Hurricanes' top-six group. The Maple Leafs made a mistake giving up on him so quickly.

14 Never Chased: Stephane Robidas

Rick Osentoski-USA TODAY Sports
advertising

In the 2014 offseason, the Toronto Maple Leafs signed Stephane Robidasto a three-year, $9 million contract. This came as a huge shock because Robidas just came off two broken legs the year before with the Anaheim Ducks. With the term and his age at 37, this automatically seemed like a bad idea from the start.

Robidas would only play one season of that contract because, like many worried, he ended up hurting his leg again. He tried to comeback from the injury, but it was simply out of the question. This was a horrible signing due to circumstance. If Robidaswas healthy, he could have been a good piece for the MapleLeafs.

13 Kept:Brad Boyes

Kim Klement-USA TODAY Sports

The Maple Leafs made a big splash during the 2002-2003 season when they acquired Owen Nolan from the San Jose Sharks. Although Nolan was a superstar at that time, it was clear that he was on the decline. The biggest piece of the deal going back was Brad Boyes and this would end up being a mistake by the MapleLeafs.

Although Boyes would only play a single game for the Sharks, he became a star for the Boston Bruins and then St. Louis Blues. His best season came in 2007-08 when he scored 43 goals and registered 65 points in 82 games. He would go on to reach a career high in points the next season with 72 and ended up being an elite player that the Leafs could have used.

12 Never Chased: Andrew Raycroft

Bob DeChiara-USA TODAY Sports
advertising

During the 2006 offseason, the Maple Leafs acquired Andrew Raycroft from the Boston Bruins for prospect Tuukka Rask. Raycroft was coming off a very bad season with the Bruins, but the Leafs were desperate for a starting goalie. Yet, Raycroft could not find his game in Toronto and quickly was off the team.

Rask, on the other hand, turned into a franchise goalie for the Boston Bruins and is still there today. This is a trade that the Leafs will never forget because they had goalie issues for years after this and would have been perfectly fine with Rask. Rask still has a few more years left in his prime, while Raycroft has been out of the NHL for years now.

11 Kept: Alex Steen

Jasen Vinlove-USA TODAY Sports

At one point in the time, the Maple Leafs had the talented Alex Steen (#20) on their roster and in theory, that sounds amazing. Yet, the Maple Leafs gave up on the then struggling winger and sent him to the St. Louis Blues for Lee Stempniak. This trade would end up hurting them pretty quickly and still impacts them today.

Steen is a dominant player for the St. Louis Blues and has been since his arrival. Meanwhile, Stempniak did not last very long in a Maple Leafs uniform. Stempniakis not a bad player whatsoever, but at the end of the day, Steen outclasses him. The Leafs still must be kicking themselves over this mistake.

10 Never Chased: Jeff Finger

via jdmminitruckparts.com
advertising

When the Maple Leafs signed Jeff Finger to his atrocious deal, it was clear that this was a monumental mistake by the club. At the time, Finger had only played one season in the NHL for the Avalanche and definitely did not show enough to deserve a four-year, $14 million deal.

Once Finger joined the Maple Leafs, it was apparent that it was a huge mistake of a signing.Finger would only two seasons with the Leafs before being sent down to the Marlies for the remaining two years. At the end of the day, this will always be looked at as one of the worst signings in NHL history and most puzzling.

9 Kept: Phil Kessel

Aaron Doster-USA TODAY Sports

Although Phil Kessel's tenure with the Maple Leafs was full of drama, the team may have given up on the star winger too shortly. It is understandable that the Leafs would not have been able to afford his contract in a few seasons, but realistically, he still could have been a spectacular player for the club as they are reaching contention.

This is apparent by the fact that theLeafs willingly brought in aging winger Patrick Marleau that will pay him over six million dollars for three seasons. They could have kept Kessel a bit longer at a similar price and had a far better player. Not to mention, Kessel has won two Stanley Cups since joining the Penguins two years ago.

advertising

8 Never Chased: Vesa Toskala

via thestar.com
advertising

Gasp. Vesa Toskala is one of the worst decisions the Leafs have ever made, but he was supposed to have a lot of promise. Before being traded to theLeafs, Toskala was a very talented backup goalie for the Sharks and deserved to be a starter. However, it became clear that Toskala could not handle the pressure of Toronto.

Toskala would last three seasons with the Maple Leafs and had a save percentage about .900 only once. Besides this abysmal stat line, Toskala continued to grow worse year-by-year and eventually was given up. Everyone will remember the fluke goals he let in on numerous occasions and how much of an overall letdown he was.

7 Kept: Bernie Parent

via nhl.com

It is easy to see that the MapleLeafs have struck out with their goaltenders numerous times. In 1973, the Maple Leafs traded away Bernie Parent's rights to the Philadelphia Flyers and every hockey fan knows what came from that. Parent became a franchise goalie for the Flyers and the best player on their roster.

The two seasons after the trade, Parent was the best goalie in the entire league and led the Flyers to two Stanley Cup championships. Meanwhile, the Leafs struggled to gain any ground those seasons and could have used Parent in their net. The Leafs did not realize the immense talent they had and it will always be a trade they regret.

6 Never Chased: Tom Kurvers

via sportsnet.ca
advertising

Tom Kurvers is a victim of circumstance when it comes to this list because of what the Maple Leafs gave up to acquire him. The Leafs traded their first round pick in 1991 for Kurvers' services and that would end up being arguably the biggest mistake in the franchise's history.

That season, the New Jersey Devils would select Hall of Fame defenseman, Scott Niedermayer with that pick and the rest is history. Niedermayer led the Devils to three Stanley Cups, while Kurver swould leave the team after three seasons. This is just a monumental mistake by the Leafsand will never be forgotten.

5 Kept: Doug Gilmour

Tom Szczerbowski-USA TODAY Sports

The Toronto Maple Leafs should never have gotten rid of Doug Gilmour because he was the heart and soul of the team. Gilmour was their franchise player when Wendell Clark left the team and was the reason the Leaf shad any success. Yet in 1997, the Leafs decided to move on from Gilmour and trade him to the Devils.

The Maple Leafs received, metaphorically, nothing but a pack of pucks for their franchise player. Gilmour would end up having a strong end of his career and the Maple Leafs could have used his leadership when they found themselves back near the top of the league. Overall, they needed Gilmour and they let him go too soon.

4 Never Chased: Mike Komisarek

via pensionplanpuppets.com
advertising

At the time of the Mike Komisarek signing, he was one of the best shutdown defensemen in the league, so it made perfect sense. Yet,Kominsarek's game quickly declined and he ended up being an atrocious pickup by theLeafs.He simply was not worth the five-year, $22.5 million dollar contract and it hurt the Maple Leafs in the process.

From the start of the contract, Komisarek started to get injured often and his point totals fell off entirely. He would end up playing only one full season under this contract and only managed ten points in the process. Eventually, Komisarek would be buried in the AHL until his contract expired and then finished his career with the Carolina Hurricanes in 2013-14.

3 Kept: Lanny McDonald

Tom Szczerbowski-USA TODAY Sports

When Lanny McDonald was a member of the Toronto MapleLeafs, he was one of the best players in the entire league and was a proven leader. Yet, McDonald was traded away due to the fact that Maple Leafs' general manager, Punch Imlach, did not like his teammate Darryl Sittler and made the deal to spite him. The trade was met with outrage and rightfully so.

The politics behind this trade is already bad enough, but McDonald would end up being an even better playing once leaving the MapleLeafs. After a few seasons with the Rockies, McDonald was traded to the Calgary Flames and in return, captained them to the Stanley Cup in 1988-89 during his final season in the NHL.

2 Never Chased: David Clarkson

Ed Mulholland-USA TODAY Sports
advertising

David Clarkson (#23) is the prime example as to why you should never give a free agent a huge contract after one solid season. Clarkson hit the30 goal mark in the 2011-12 season and had a decent season during the lockout year, but his seven-year, $36.75 million contract was a huge mistake from the start.

Once Clarkson joined his boyhood team, he turned back into the fourth line player he was for the majority of his career. Clarkson registered less than twenty points in each of his two seasons with the Leaf sand eventually was traded to the Columbus Blue Jackets for the injured Nathan Horton. Overall, this was just an abysmal signing and should have never happened.

1 Kept: Darryl Sittler

Tom Szczerbowski-USA TODAY Sports

Darryl Sittler (#27) was recently addressed in this article and he is also a player that they should have kept. Yet, due to the management of the Leafs,Sittler saw himself forced out of the city. Besides butting heads with Imlach, he also grew distant to Leafs owner Harold Ballard because of the way that the situation was being handled and eventually asked for a trade out.

If Sittler was treated with respect, he most likely would have spent his entire career with the Maple Leafs. When the Leafs traded him to the Flyers, he had three spectacular seasons with them and even had a record 10 point game against the Bruins. His situation was just handled so poorly and he deserved far more respect.

advertising

More in NHL