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Top 15 Worst Trades In Philadelphia Flyers History

While the most infamous drought in the NHL right now is the Toronto Maple Leafs about to reach 50 years without a Stanley Cup, there are other fanbases around the NHL that are starving for a championship. Philadelphia is one of them, as they're now on a 40-plus year drought, with their last Stanley Cup coming back in 1975. Fans are yearning for the days of the Broad Street Bullies and while the Flyers' makeup has usually consisted of a tough team, it just hasn't translated to championships.

They've come close on multiple occasions, making the finals in 1976, 1980, 1985, 1987, 1997 and 2010. They've made the conference (or semi) finals an additional seven times, but came up short.

They've had plenty of talented teams in their drought, but one constant weakness has been their goaltending and overpaying for certain players. Like with any team, they also have plenty of regrettable trades, which we'll explore in this article. While some moves can be debated as to whether they were terrible, or simply a risk that didn't pay off, the bottom line is, this is a franchise that doesn't seem to be all that close to their next Stanley Cup.

Here are the 15 worst trades in Flyers history.

15 Breaking Up The Legion Of Doom

via nhl.com

Arguably the Flyers' best team since their 1975 Stanley Cup, the 1996-97 Flyers seemed to be destined to bring a cup back to Philly. Eric Lindros had emerged as one of the greatest in the game and the team had formed a lethal Legion of Doom line consisting of Lindros, John LeClair and Mikael Renberg. Following a sweep in the '97 final to the Red Wings, this line was broken up, as Renberg was dealt that summer for Chris Gratton from the Tampa Bay Lightning.

What's ironic about this trade is that the exact same trade would occur just a couple of seasons later, with Gratton being traded back to Tampa for Renberg. Just what was the point of this? Why break up a formidable line? By the time Renberg returned in 1999, the same magic just wasn't there with the trio of Lindros, LeClair and Renberg.

14 Adam Oates As Short Term Rental

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Rental players are always a risk and either come back to make the GM look like a genius or a short-sighted idiot. With the 2001-02 season winding down and the Capitals out of playoff contention, the Caps traded Oates, a once elite playmaker and terrific faceoff man to Philly for Maxime Ouellet, as well as the first, second and third round selections in the 2002 draft.

Unfortunately for the Flyers, the move of bringing in Oates did not bring them any kind of success. Like many years of the 2000s, the Flyers were ousted in the first round, this time by the Ottawa Senators. Oates played just 14 regular season games for Philly, scoring 10 points and adding two assists in the Flyers' five playoff games.

13 Michal Handzus for Kyle Calder

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It's easy to forget based on the Michal Handzus we saw in his later years in the NHL, but Handzus was a very effective player for the Flyers in the early to mid 2000s. In two full seasons in Philly, Handzus was a responsible defensive player and put up seasons of 44 points and 58. He also played all 82 games in both his seasons in Philly. He also added 18 points in 31 playoff games.

The Flyers acquired Kyle Calder from the Blackhawks in exchange for Handzus and Calder only lasted 59 games in Philly, potting 21 points and a dreadful -31 rating. He was then sent back to Chicago later that year. For a team to get rid of a player that fast shows you just how badly it turned out for them.

12 Future Playoff Hero Justin Williams Shipped For Danny Markov

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Justin Williams is, or at least was, the type of player that teams wanted for a playoff run. It's why the Capitals went out and got him in the summer of 2015, and Williams has also been dubbed Mr. Game 7. Unfortunately for Williams, his Flyers career only lasted three seasons and he was constantly marred by injuries, including a torn ACL suffered in 2003.

Williams made it back for the 2003-04 season, but he was traded near the deadline to the Carolina Hurricanes, in exchange for defenceman Danny Markov. Markov proved to be a solid defenceman for the Flyers, but Williams saw his career take off in Carolina. Following the lockout, Williams set career highs for Carolina in 2005-06, scoring 76 points and adding 18 points in 25 playoff games, en route to the Cup.

Williams has continued to be a clutch playoff performer, and even won the 2014 Conn Smythe.

11 Acquiring Pavel Kubina A Tad Too Late

via blesk.cz

Back near the 2012 trade deadline, the Flyers needed help on the blueline and acquired Pavel Kubina from the Tampa Bay Lightning for John Kalinski, a second round pick and a fourth round pick. Kubina was a solid player back in his prime, but by 2012 he was a shell of his former self. Kubina was not the same player who scored 17 goals for Tampa Bay in their championship season of 2003-04.

Kubina would play just 17 regular season games as a Flyer, and five playoff games. He quickly proved to be a liability to the Flyers' defensive corps rather than an asset. Kubina would score just four points in the regular season and one point in their first round playoff loss to the Penguins.

10 Trading Scottie Upshall For Dan Carcillo

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Dan Carcillo somehow always managed to find himself on good teams, continuously finding a role as the agitator. One good team he ended up with was the Flyers of the late 2000s, as the Flyers acquired Carcillo in a trade with the Coyotes at the 2009 trade deadline. Carcillo was an agitator all right, but Upshall provided a lot of leadership and was a heart-and-soul type of player.

Carcillo played his role, but he often took costly penalties. In the 2009 playoffs, with the Flyers up 3-0 in Game 6 of the opening round against Pittsburgh, Carcillo decided to fight Max Talbot. The Penguins scored 14 seconds after the fight and rallied to take the game and the series. Carcillo would two additional seasons with the Flyers, while Upshall proved to be the more productive player.

9 Cap Cutting Move Backfires

via sonsofpenn.com

Following their run to the Stanley Cup in 2010, the Flyers had to make some cost cutting moves and one of their solutions was to trade the clutch, but often injured Simon Gagne to the Tampa Bay Lightning. The Flyers received Matt Walker and a fourth round pick in return. Walker ended up spending most of his time in the AHL as a Flyer. At the time of the trade GM Paul Holmgren said of Walker: "We like the way Matt plays. He's a character-intense player. He plays physical. He's a stay-at-home guy that is a good penalty killer. On our team he can buy us dirty minutes and not be a liability, but be a positive force and help and defend our own zone."

While Holmgren's hand was kind of forced in trading Gagne, he would have been far better taking a low draft pick than Walker, who had three years and a $1.7 million cap hit remaining on his contract.

8 JVR For Luke Schenn

via zimbio.com

The Flyers just barely missed out on landing Patrick Kane in the 2007 draft, who went first overall to the Blackhawks. The Flyers got the no.2 overall pick and used it to draft James Van Riemsdyk. JVR showed some promise in Philly, but overall the Flyers weren't satisfied with the production of their second overall pick and he was having trouble staying healthy. Their response was to grab Luke Schenn from the Leafs, another underperforming high draft pick.

Since this deal has gone down, Schenn has since been traded to the L.A. Kings after never amounting to more than a third pairing defenceman for Philly. While the Leafs have continued to struggle JVR has since become a 30-goal scorer and he's probably happy to now have Auston Matthews with him.

7 John Carlson's Rights Shipped To Washington

Geoff Burke-USA TODAY Sports

Prior to the 2008 draft, the Flyers traded their 27th overall pick to the Washington Capitals for Steve Eminger, and a 3rd round pick. Eminger would play just 12 games as a Flyer and totaled two assists and eight penalty minutes. Who did the Capitals get with that draft pick? John Carlson. Up until last season, Carlson spent six years in Washington never missing a game due to an injury and he reached career highs in 2014-15 with 55 points. The Flyers would certainly love to have a player like him right now, as he'd make half of a formidable duo next to Shayne Gostisbehere.

It sure is a head scratcher to think of how the Flyers thought Eminger was worth a first round pick.

6 Bernie Parent Shipped To Toronto

via nhl.com

The Flyers almost blew their chance at their only Stanley Cups when they traded future Hall of Fame goalie Bernie Parent and a second round pick to the Toronto Maple Leafs. In return, the Flyers received Bruce Gamble, Mike Walton and a first-round draft pick. The Leafs would use that first round pick to draft Rick Kahoe, who would amass six 30-goal seasons and even tallied 55 goals in the 1980-81 campaign.

None of thos pieces that came back in the trade contributed for Philly and the man they took with that first-round pick, Pierre Plante, played just two games with the team. Luckily for Parent, going to Toronto gave him the chance to learn under Jacques Plante, and after his contract expired the Leafs traded his rights back to Philly in 1973. Parent would then have a career year in 1973-74, recording a .933 SV% and 1.89 GAA, leading the Flyers to their first Stanley Cup.

Can you imagine the Flyers almost let him slip away? Oh well, all's well that ends well.

5 Sergei Bobrovsky Slips Away

Bruce Fedyck-USA TODAY Sports

Sergei Bobrovsky showed signs of being a franchise goalie in Philly, but like many young goalies, he had trouble finding consistency in his game. In June of 2012, the Flyers traded the young Russian netminder to the Columbus Blue Jackets in exchange for a second round pick and two fourth rounders. The Flyers chose Anthony Stolarz and Taylor Leier with two of those picks and wound up shipping a fourth rounder in a separate trade.

The very next season, Bobrovsky would win the Vezina Trophy, posting a .932 SV% and a GAA of just 2.00 in the lockout shortened season of 2012-13. Bobrovsky has since led the Blue Jackets to a playoff berth in 2013-14 although the Blue Jackets are now having their own struggles.

For now the trade looks bad on Philly, but that could change if Bobrovsky's career dwindles.

4 Bryzgalov Becomes Another Flyers Footnote

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In late June of 2011, the Flyers were coming off yet another disappointing playoff exit. After years of journeymen goaltenders, the Flyers decided enough was enough and they decided to trade for the rights to impending UFA Ilya Bryzgalov. The Flyers landed Bryz from the Coyotes for Matt Clackson, a 2012 third-round pick and a conditional 2011 third-round pick.

Bryzgalov's tenure in Philly was a disaster after signing a massive contract at nine years and $51 million. It turned out Bryzgalov wasn't well liked by his teammates in Phoenix and he was well insulated in Dave Tippet's defensive system. His weaknesses were soon exposed and following the 2012 lockout in which compliance buyouts were allowed, the Flyers used one on Bryz, which will pay him $23 million, coming out to $1.64 million for 14 seasons.

3 Acquiring Pat Falloon

via gunaxin.com

Despite Patrick Falloon being a disappointment for the San Jose Sharks, the Flyers decided to trade for him in 1995. In return they sent Martin Spanhel to San Jose, along with a first and fourth round pick. The first round pick that went to San Jose was eventually sent to Phoenix, who used it to take Danny Briere.

As for Falloon's tenure in Philly, he had a decent 1995-96 season, scoring 22 goals and 48 points, but would never top 22 points a season in his following two years in Philly. Falloon also failed to produce for the team in the playoffs, only managing nine points in 26 playoff games.

While they ended up landing Briere about a decade later, the Flyers sure would have loved to have him his whole career.

2 Patrick Sharp For Who?

via bleacherreport.com

Patrick Sharp had so many successful seasons in Chicago that we forget he was originally a Phildaelphia Flyer. In December of 2005, the Flyers sent Sharp and Eric Meloche to the Chicago Blackhawks for Matt Ellison and a third round choice in the 2006 draft.

Ellison would play just seven games for the Flyers and only mustered one assist. While Meloche wouldn't amount to much in Chicago, Sharp became one of the key pieces to the Blackhawks' dynasty, as he became one of the league's better forwards and helped the Blackhawks win three Stanley Cups before being shipped to Dallas.

Sharp would directly come back to haunt the Flyers, as he scored four goals and two assists in Chicago's Stanley Cup Final win over Philly in 2010. That had to hurt.

1 Too Much For 'Not Quite The Next One'

via gofansgo.com

This entry will be highly debated and I understand that. The Flyers were completely devoid of talent in the early '90s and with Eric Lindros being touted as "the next one" Philly must have felt unloading anybody of value was worth it.

A year after being drafted by the Quebec Nordiques, Lindros was still refusing to play in Quebec and the NHL had to convince the Nordiques to seek out a deal, as they didn't want a young star like Lindros sitting.

There were two deals on the table for Lindros; one from Philly and one from New York. An arbitrator ruled in favor of a trade package put together by the Flyers, which sent Ron Hextall, Steve Duchesne, Mike Ricci, Kerry Huffman, Peter Forsberg, a first-round pick in the 1993 NHL Entry Draft, $15 million, and future considerations. The arbitrator would also add Chris Simon and a 1994 first rounder to the deal.

While Lindros was a dominant player, injuries ultimately derailed his career, while the Nordiques used this trade to build a Stanley Cup contender, albeit as the Colorado Avalanche.

This is just a case of the price simply being too high in the end for Lindros. You have to wonder if Philly could have been what the Nordiques/Avalanche eventually became had they not done this trade.

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Top 15 Worst Trades In Philadelphia Flyers History