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It’s easy to forget how sad of a franchise the Chicago Blackhawks used to be. Today, they’re the gold standard of how to succeed in the salary cap NHL, as they’ve been able to content for the Stanley Cup year after year, despite having to unload star players every year to make cap room.

However, before 2010, the Blackhawks went 49 years without winning a Stanley Cup. There were times when the Chicago market had soured on the team, due to the controversial practices of late owner Bill Wirtz. Wirtz earned the nickname “Dollar” Bill due to his frugality and stubborness. Wirtz would black out home games on TV if the arena wasn’t sold out, alienating many Hawks fans. He also had many star players traded once he felt their price tag had gone too high, not allowing the ‘Hawks to reap the benefits of acquiring stars.

If you could believe it, the Blackhawks were once named the worst franchise in sports by ESPN back in 2004.

No other franchise in sports has turned things around quite like the Blackhawks in the past decade, but there’s still plenty of regretful history with this team. Here, we will look at the 15 worst trades in Blackhawks history. This will probably make fans appreciate how well oiled a machine the Hawks are today.

15. Rental Deal Backfires

Bruce Fedyck-USA TODAY Sports

Bruce Fedyck-USA TODAY Sports

In a surprise twist, we’ll begin this list with a trade that happened a year ago near the trade deadline. As usual, the Blackhawks wanted to load up for another run at the Stanley Cup, looking for their fourth Cup in seven seasons. Searching some depth up front, the Hawks traded 23-year-old center Phillip Danault and a 2nd round pick to the Montreal Canadiens for veterans Dale Weise and Tomas Fleischmann. Weise was in the middle of a career year and a pending UFA, so the Hawks figured Weise would give them his best hockey before he hit the free agent market. In Fleischmann, they knew they were getting an experienced player who wouldn’t be intimidated by the playoffs.

Well, as it turned out, Weise failed to score a goal with the Blackhawks and soon became a healthy scratch. He scored one goal in four playoff games. Fleischmann did his part as a rotational forward, but made little impact as well. Neither re-signed in Chicago.

Meanwhile, Danault has emerged in Montreal as a full-time NHL player and has even gotten top line minutes this season, as the Habs have been decimated by injury.

14. Ladd Re-Acquisition Fails

Billy Hurst-USA TODAY Sports

Billy Hurst-USA TODAY Sports

We go to another rental move last season by Chiacgo that didn’t pay off. While no one expected Andrew Ladd to remain in Chicago beyond the 2015-16 season when he was acquired at the deadline, he was expected to help the Hawks make a long playoff run. Ladd was acquired along with Matt Fraser and Jay Harrison from Winnipeg for Marko Dano, a 1st round pick and a conditional third rounder. The Hawks had Ladd in their dominant 2010 lineup, so this trade was made in hopes Ladd would provide more playoff magic back in Chicago. Ladd would record 12 points in 19 regular season games, then two points in Chicago’s opening round loss to St. Louis.

As expected, Ladd left the team in free agency, so Chicago essentially had nothing to show for this trade, while giving up some valuable pieces in Dano and a first rounder.

13. Bryan McCabe To Toronto

via religionduhockey.wordpress.com

via religionduhockey.wordpress.com

Bryan McCabe had his faults as a player, but in his prime, he was one of the league’s better offensive defencemen and was very useful on the power play. He moved around quite a bit in his career, and played in Chicago for one season (1999-00). He recorded just 29 points in 72 games, so the Blackhawks felt he was expendable, sending him to Toronto for Alexander Karpovtsev and a fourth round draft pick. In case you’re wondering why you never heard of Karpovtsev, it’s because he didn’t amount to much in his NHL career.

In Toronto, McCabe formed a good duo with Tomas Kaberle and his career-season came in 2005-06 when he recorded 68 points. All things considred, he carved out a good career for himself, but the Hawks gave him up for essentially nothing.

12. Rights To Marco Sturm To San Jose

via evl.info

via evl.info

While Marco Sturm is remembered mostly for being part of the trade that sent Joe Thronton to San Jose, he was a useful player that managed to play 938 games in the NHL. When you compare that to the rest of his draft class (1996) that’s exceptional. The ’96 class is one of the worst in NHL history, but Sturm proved to be among the draft’s best. The Hawks had a chance to draft Sturm that year, but traded the rights to the 21st overall pick to the San Jose Sharks, who took Sturm.

In return, the Hawks received two second round picks (Remi Royer and Geoff Peters) who played a total of 18 NHL games between them. Chicago didn’t know it, but 1996 was not the draft year to acquire more picks. They should have just stuck with Sturm.

11. Saad Day For Chicago

Dennis Wierzbicki-USA TODAY Sports

Dennis Wierzbicki-USA TODAY Sports

Now, this entry isn’t to fault the Blackhawks for trading Brandon Saad. They really didn’t have a choice, as they had just signed Jonathan Toews and Patrick Kane to monstrous extensions and they had to find some salary cap space. The only gripe you could make is that perhaps they should have unloaded some of the team’s other contracts sooner. Perhaps they could have tried to move Marian Hossa instead and retain a young star like Saad.

All things considered, the Hawks got a decent return. They sent Saad, Alex Broadhurst and Michael Paliotta to Columbus, landing Artem Anisimov, Marko Dano, Corey Tropp, Jeremy Morin and a fourth round pick. Saad has paid dividends for Columbus and will play out his prime with the Blue Jackets.

Again, it’s just unfair to the Hawks that the salary cap world has forced them to trade stars away.

10. 2010 Fire Sale

Anne-Marie Sorvin-USA TODAY Sports

Anne-Marie Sorvin-USA TODAY Sports

If there was one example as to how the Blackhawks have suffered from the salary cap era, it’s this trade here. After ending a 49-year Stanley Cup drought in 2010, it was expected that the ‘Hawks would have a chance to repeat. That is until, the Hawks took a look at their salary cap and realized they had to unload some contracts, or players due for raises.

In the summer of 2010, the Hawks traded Dustin Byflugien, Andrew Ladd, Akim Aliu, Brent Sopel and Ben Eager (in seperate deals) to the Atlanta Thrashers, which landed them Jeremy Morin, Marty Reasoner, Joey Crabb, Ivan Vishnevskiy and multiple draft picks.

The trades set Chicago back a couple of years. The team lost a lot of depth and would lose in the opening round of the playoffs the following two years. That damn cap…

9. Radim Vrbata To The Desert

Brace Hemmelgarn-USA TODAY Sports

Brace Hemmelgarn-USA TODAY Sports

This trade was made before the Blackhawks emerged as Stanley Cup contenders. The team had just drafted Patrick Kane as 2007’s first overall pick and Jonathan Toews was about to make his NHL debut. The Hawks decided to unload Radim Vrbata to the Coyotes in exchange for Kevyn Adams.

This trade was extremely lopsided. Vrbata recorded 56 points in the 2007-08 season, while Adams would record just two assists for Chicago and never played in the NHL again. Vrbata has continued to be a reliable top six forward and needless to say, the Hawks could have used his presence in the late 2000s. While they did fine without him, just imagine them throwing Vrbata into the mix of their stacked roster.

8. Parenteau To The Rangers

Charles LeClaire-USA TODAY Sports

Charles LeClaire-USA TODAY Sports

Dale Tallon was still in charge of the Chicago Blackhawks at this time. Chalk this up to a bad few days for the current GM of the Florida Panthers. After trading Vrbata earlier that summer, Tallon traded P.A. Parenteau to the New York Rangers for a conditional seventh round pick. Parenteau had played five games for the Hawks in their 2006-07 season.

He was basically traded for nothing, as the Hawks never used the conditional pick. While Parenteau spent the next few years in the minors with the Rangers, he eventually emerged as a top six forward. After moving to Long Island to play with the Islanders, Parenteau recorded a 67-point season in 2010-11. He would also put up 43 points in a 48-game season with the Avalanche in 2013.

Hey, that’s better than nothing, right?

7. Hawks Trade Doug Wilson Before Cup Run

Charles LeClaire-USA TODAY Sports

Charles LeClaire-USA TODAY Sports

This entry is more due to a sentimental factor. Yes, Doug Wilson was on the tail end of his NHL career, but the Blackhawks had emerged as a serious Stanley Cup contender prior to the 1991-92 season and Wilson deserved to be a part of that. However prior to the 1991-92 season, where the Blackhawks reached the Stanley Cup Final, Wilson was traded to the expansion San Jose Sharks for Kerry Toporowski and a 2nd round pick.

While Wilson didn’t exactly light the world on fire in San Jose, while suffering multiple injuries, he deserved to finish his career in Chicago. Seeing him in a Stanley Cup Final would have been a treat for Blackhawks fans. Wilson played his final two NHL seasons in San Jose and serves as their general manager today.

6. Bye Bye Belfour

via tumblr.com

via tumblr.com

The Blackhawks had not one, but two future Hall of Fame goalies on their roster in the ’90s and neither finished their career with the Blackhawks. We’ll start here with the trade of Eddie The Eagle Belfour.

Belfour was a five-time All-Star in seven-plus seasons with the Blackhawks, won the Jennings trophy three times, was the rookie of the year and won two Vezina trophies. He was a main reason the Blackhawks contended in the playoffs for much of the ’90s, but by 1996-97, he had become too expensive for the stingy Blackhawks. In midst of another great season in Chicago, Belfour was dealt to San Jose for Chris Terreri, Michal Sykora and Ulf Dahlen.

Goaltender Terreri would play just 28 games for Chicago, Sykora would only record 14 points in 56 games with the ‘Hawks while Dahlen played just 30. After a short run in San Jose, Belfour would sign with the Dallas Stars and helped them to the 1999 Stanley Cup.

5. Hawks Sacrifice Offense (And The Cup?)

via amazonaws.com

via amazonaws.com

This trade is criticized as one of Mike Keenan’s worse moves while in charge of the Blackhawks. Following a first round upset after winning the President’s Trophy, Keenan wanted to shake things up. He sent center Adam Creighton and winger Steve Thomas to the New York Islanders for Brent Sutter and winger Brad Lauer. The idea behind the trade was to get more defensively responsible players, even if it meant sacrificing the offense Thomas and Creighton provided.

As it turned out, the Hawks did in fact make a deep run to the Stanley Cup Final in 1992, but were completely outmatched by the Pittsburgh Penguins in the final, losing in four straight. Many ‘Hawks fans cite this as the trade that cost the Hawks the Stanley Cup that year.

4. Chelios Wants To Keep Playing

via espn.com

via espn.com

Acquiring Chris Chelios for Denis Savard was perhaps the best trade in Blackhawks history, but trading Chelly away was one of the worst. In the 1998-99 season Chelios was still the team captain and while he was in his late 30s, he still had plenty of good hockey in him. The Hawks though, thought he was done and GM Bob Murray said there was a front office job waiting for Chelios after his contract would expire in 2000.

Chelios still wanted to play though, so the Hawks traded their captain to archrival Detroit for Anders Eriksson and two first round draft picks. Giving Chelios to the Wings made them a stronger contender and further weakened the ‘Hawks. After a decade of Chicago showing so much promise, the late 90s saw a series of terrible trades that sunk the team into obscurity.

As we know, Chelios would play over another decade in the NHL.

3. J.R. Goes To Phoenix

via bigcommerce.net

via bigcommerce.net

Jeremy Roenick was another popular Blackhawks player that gave them many exciting seasons, but he too, was discarded when the price tag got too high. Roenick was an elite scorer in the league, having scored 596 points in 570 games with the Blackhawks. He was a star, but owner Wirtz didn’t want to pay him like one. At 26 years old, Roenick was an RFA and was $5 million apart in talks with the team for a five-year contract.

And so, the Hawks traded J.R. to the Phoenix Coyotes for Alexei Zhamnov, Craig Mills and a first round pick. Zhamnov was projected to be the next Sergei Fedorov (ha!) and the ‘Hawks thought he’d be a better option at a cheaper price. Roenick got the money he wanted in Phoenix and the ‘Hawks ended up paying $15 million for Zhamnov on a five-year deal, far more than they expected to pay. Oh and he wasn’t the next Fedorov.

2. The Dominator Is Discarded

via yahoosports.com

via yahoosports.com

The Chicago Blackhawks began the ’90s with two future hall of famers between the pipes but had traded both before the decade ended. Belfour remained their starter through much of that time, but Chicago would trade perhaps the best goaltender of the 90s in Dominik Hasek. In his prime, Hasek carried the Buffalo Sabres to multiple playoff runs and went all the way to the ’99 Final.

Considering the talent the Blackhawks had earlier in the decade, perhaps Hasek could have pulled off a similar feat for Chicago. Prior to the 1992-93 season, Keenan capped off a series of bad moves by trading Hasek to Buffalo for Stephane Beauregard and a fourth rounder. Three days later, he traded Beauregard to Winnipeg for Christian Ruuttuu. It took Hasek a while to develop, but he was a promising prospect. With Jimmy Waite in the system though, Keenan felt Hasek was expendable.

However Waite proved to be a terrible backup for Belfour while Hasek won multiple Vezina trophies and was a two-time NHL MVP.

1. Phil Esposito Gets Traded For His “Big Mouth”

via thehockeywriters.com

via thehockeywriters.com

This trade seems so petty and it basically gave the Bruins one of the key pieces they needed to form one of the most dominant teams in NHL history. The Blackhawks could have formed a dynasty, as they had Bobby Hull, Stan Mikita, Pierre Pilote, Glenn Hall and a young Phil Esposito. Despite that stacked talent, Esposito still managed to be the fourth-highest scorer on the team in his first three seasons.

At the end of the 1966-67 season, Esposito, known for his outspokenness, had a little too much to drink at an end-of-season party. He blurted out to coach Billy Reay and GM Tommy Ivan “We’ve got a great team here, you could almost have a dynasty, but you two are gonna screw it up.”

Well it turns out Esposito was right. He was shipped to Boston along with Ken Hodge and Fred Stanfield for Gilles Marotte, Pit Martin and Jack Norris. Esposito would record 1,590 career points and had one of the most decorated NHL careers of all time. The Blackhawks meanwhile, would underachieve and screwed things up, as Espo predicted.

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