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NHL Free agency: Most long-term contracts will end in trade or buyout

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Exactly six years ago Friday, the Toronto Maple Leafs made one of the most infamous free agent signings in the salary cap era when they inked David Clarkson to a seven-year, $36.75 million contract. It was a dubious signing from the very beginning due to Clarkson’s age (he was already 29 years old) and lack of consistent, top-line production in the NHL. Adding to the absurdity was the reception of the contract in Toronto (comparing him to Wendel Clark) and the way then-general manager Dave Nonis defended the signing from any and all criticism by saying, “I’m not worried about six or seven right now. I’m worried about one. And year one, I know we’re going to have a very good player. I believe that he’s got a lot of good years left in him.”

How did that work out?

In year one Clarkson scored five goals in 60 games, was a colossal bust, and was then traded to the Columbus Blue Jackets halfway through year two of the contract for Nathan Horton, another free agent bust from the same offseason whose career would be derailed and ultimately ended by injury. The Maple Leafs knew Horton would never play again and the whole trade was nothing more than a way to shed an albatross contract that looked to be a mistake from the start. It was an obvious — and ultimately legal — circumvention of the league’s salary cap.

Clarkson’s contract is far from the only one that has gotten general managers in trouble for signing a player for too many years in free agency. Almost every time the justification is similar to the one Nonis gave for the Clarkson signing: We’re not worried about four or five years, we just want to win right now.

Most of them never win “right now,” and almost all of them are looking for a way out within two years.

Between the summers of 2009 and 2016 there were 35 unrestricted free agents signed to contracts of five years or longer.

What sort of return did teams get on those investments?

Let’s start with this, showing the result of each signing.

[Related: PHT 2019 Free Agent Signing Tracker]

This only includes players that actually changed teams as UFA’s. It does not include re-signings of players still under contract with their current team (contract extensions), or the re-signing of restricted free agents.

• Fourteen of the 35 players were traded before the end of their contract term. That includes nine players that were traded before completing three full seasons with their new team. Most of these trades were salary dumps or an exchange of undesirable contracts.

• Ten of the contracts ended in a buyout, usually after three or four seasons.

• There are only three players signed during this time period that are still playing out their contracts with their current teams: Zach Parise and Ryan Suter in Minnesota, and Michael Frolik with the Calgary Flames. The latter has been mentioned in trade rumors for more than a year now.

• Only four players played out the entire term with the team that signed them: Paul Martin with the Pittsburgh Penguins, Anton Stralman with the Tampa Bay Lightning, Brian Gionta with the Montreal Canadiens, and Dan Hamhuis with the Vancouver Canucks.

• Three players had their careers ended by injury before the duration of the contract: Marian Hossa with the Chicago Blackhawks, Ryane Clowe with the New Jersey Devils, and Mattias Ohlund with the Tampa Bay Lightning.

• On average, those 35 players played out just 57 percent of their contract term with the team that signed them. Fourteen of them played out only half of the contract or less.

• If you want to go with the “I don’t care what happens in six years as long as we win the Stanley Cup with this player” argument, the only players in the above sampling that actually won a Stanley Cup with the team that signed them during their contract were Hossa in Chicago and Matt Niskanen and Brooks Orpik in Washington. The only others to even play in the Stanley Cup Final were Anton Stralman, Valtteri Filpulla, and Matt Carle in Tampa Bay, and Brad Richards with the New York Rangers (he was bought out the following summer after three years of a 10-year contract).

What did teams learn from this sampling?

Mostly nothing, because they have kept doing it.

Between the 2016 and 2018 offseasons there were 13 UFA contracts of five years or more signed, and the early returns are already looking disastrous.

In the summer of 2016 the following deals were signed.

  • David Backes to the Boston Bruins for five years at $6 million per year
  • Kyle Okposo to the Buffalo Sabres for seven years at $6 million per year
  • Frans Nielsen to the Detroit Red Wings for six years at $5.25 million per year
  • Milan Lucic to the Edmonton Oilers for seven years at $6 million per year
  • Loui Eriksson to the Vancouver Canucks for six years at $5.5 million per year
  • James Reimer to the Florida Panthers for five years at $3.4 million per year
  • Andrew Ladd to the New York Islanders for seven years at $5.5 million per year

Not sure there is anybody that would look at any of those contracts just three years later and argue that any of those teams are getting what they hoped to get. Reimer has already been traded so the Panthers could give another long-term deal to a different goalie (Sergei Bobrovsky) this offseason, while the rest of the contracts have all quickly become an albatross for every team that signed them.

There were six contracts signed over the 2017 and 2018 offseasons with Alexander Radulov, Karl Alzner, John Tavares, James van Riemsdyk, Jack Johnson, and John Moore all getting contracts of five years or more.

So far the Radulov and Tavares contracts look to be the best investments and have provided the most return.

Alzner spent time in the AHL this past season, while Johnson has been the subject of trade rumors after just one season in Pittsburgh.

This offseason seven teams have decided to bet against history and take their chances on long-term deals.

  • Vancouver signed Tyler Myers to a five-year contract
  • New York signed Artemi Panarin to a seven-year contract
  • Florida signed Bobrovsky to a seven-year contract
  • Pittsburgh signed Brandon Tanev to a six-year contract
  • Nashville signed Matt Duchene to a seven-year contract
  • New York Islanders re-signed Anders Lee to a seven-year contract

History suggests that probably at least five of these players will be playing for a different team within two or three years.

The players that have had the highest chances of playing out most of their contract are the high-end players (first-or second-line forwards; top-pairing defenders) that are still reasonably close to the prime of their careers, so that might be good news for the Rangers and Panarin and maybe — emphasis maybe — Duchene and the Predators.

All of the rest? These look like textbook deals that are destined to end in a salary dump trade or a buyout within a couple of years.

If a player makes it to unrestricted free agency you should know what you are bidding on and adjust your expectations accordingly. It is usually a player that has almost certainly already played their most productive hockey in the NHL, and it is usually a player that their former team didn’t feel was worth the money or term they were going to be able to get on the open market. It is rare that a team allows a player it actually wants to re-sign and values make it to free agency.

Elite players like Tavares and Panarin are the exception.

The end result is a bidding war for a declining player that probably isn’t as good as you think, which then ultimately leads to a team paying a player to NOT play for them (buyout), or trading them for another player another team doesn’t want, or giving up a more valuable asset to entice a team to take your bad contract in a trade.

NHL Free agency: Sometimes the best way to win is to not play.

Adam Gretz is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @AGretz.

PHT Time Machine: When RFA offer sheets actually happened

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Throughout the offseason we will be taking an occasional look back at some significant moments in NHL history. This is the PHT Time Machine. Today we look back at the history of restricted free agent offer sheets and some of the wild signings and situations that have unfolded because of them.

There is probably no greater time-waster in the NHL offseason than discussing the possibility of a restricted free agent offer sheet. Every year we look at the names that are out there, and every year we discuss the possibility of a young player signing a massive contract and wondering whether it will be matched, and every year nothing ever comes of it.

There are a number of theories as to why it never happens, ranging from the more nefarious ones like GM’s wanting to keep the cost of young players down or having some sort of “unwritten agreement” among them to not poach other team’s players, to a far more reasonable one: It’s really difficult to find a perfect match where such a signing can actually happen.

Not only does a team need to have the salary cap space and the appropriate draft pick assets, but the player in question has to actually WANT to sign with the team offering the contract, and the team owning that player’s rights has to be unwilling (or unable) to match it.

That is tough to find.

We do not know how many offers actually get made, but we do know in the history of restricted free agency there have only been 35 offer sheets actually signed, and only eight in the salary cap era.

Only 13 of those offer sheets were not matched and saw a player actually change teams.

We have not seen an offer sheet signed since the Calgary Flames tried to get Ryan O'Reilly away from the Colorado Avalanche during the 2012-13 season (it was ultimately matched by the Avalanche).

This offseason, of course, is no different when it comes to the speculation, and the player that is getting the most attention is Toronto Maple Leafs winger Mitch Marner due to the team’s salary cap crunch and Marner’s reported contract demands.

Will it actually happen? History says no, but a lot of the circumstances are in place for it to at least be on the table. Speaking of history, let’s take a look back at some of the more noteworthy offer sheets in NHL history.

Hurricanes sign Sergei Fedorov

This might be the wildest offer sheet situation the league has ever seen.

During the 1997-98 season the Carolina Hurricanes were in their first year of existence after relocating from Hartford. They were losing money after the move, they were in last place in their division, and the organization had missed the playoffs in each of its final five seasons as the Whalers.

Fedorov, still fairly close to the height of his powers as an NHL superstar, was involved in an ugly contract dispute with the Detroit Red Wings and by mid-February had still not signed a contract. During the Olympic break that season (the first year NHL players participated in the Olympics) the Hurricanes, led by now Hall of Fame general manager Jim Rutherford, decided to pounce and signed Fedorov to a massive six year, $38 million contract that included a $14 million signing bonus for him to play in the final 25 games of the season, and more than $12 million in bonuses over the next four years.

It would have made him one of the highest paid players in the league.

An excerpt from a Feb. 21, 1998 Associated Press story on the signing.

Rutherford later added in the story, “This is a player in a special situation who rolled the dice, he held out, he’s a world-class player and probably one of the top-five players in the world right now. He deserves to make more money. This is part of the building blocks to being in a new market … and having a franchise player.”

The Red Wings ultimately matched the offer and Fedorov not only ended up making a ton of money to play in only a quarter of the season, he played a massive part in the team winning its second straight Stanley Cup.

But it wasn’t just the fact that a last place team in a new market made the bold move to sign a superstar to a massive offer sheet that made this so intriguing. The underlying storyline here was also the fact the owners of the teams (Peter Karmanos with the Hurricanes and Mike Ilitch with the Red Wings) had a long history of being rivals in pretty much every walk of life.

Karmanos initially tried to move the Whalers to suburban Detroit after purchasing the team in 1994 (they would have played at The Palace Of Auburn Hills) something that obviously did not sit well with the Red Wings, while the two men had extensive business operations in the Detroit area (Ilitch with Little Caesars; Karmonas with a computer software company).

They were also active players in Detroit’s amateur hockey scene that resulted in Ilitch evicting Karmanos’ major junior team out of Joe Louis arena.

So … yeah. These two guys had major beef for a long time, and adding a restricted free agent offer sheet for one of the league’s best players certainly didn’t calm things down.

At least they never tried to fight in a barn, something that nearly happened in our next situation.

The Oilers’ wild summer of 2007

Knowing what we know now about how slow the RFA market typically is, it is completely absurd to look back now and remember that the Edmonton Oilers, under the direction of Kevin Lowe, signed two offer sheets in the same summer.

It all began on July 6, 2007, when he attempted to sign Thomas Vanek to a seven-year, $50 million contract in an effort to pry him away from the Buffalo Sabres. At the time Vanek was one of the league’s best young goal-scorers and was coming off of a 43-goal season. Even though he had played just two years in the league, he had already scored 68 goals and was an emerging star.

The Sabres immediately matched the offer.

So Lowe set his sights elsewhere and three weeks later targeted the reigning Stanley Cup champion Anaheim Ducks, signing Dustin Penner to five-year, $21.5 million offer sheet.

Prior to the signing then-Ducks general manager Brian Burke had said he would match any offer sheet that Penner was signed to, but he probably was not anticipating that sort of offer. Even though Penner was coming off of a 29-goal season for the Ducks, he had still only played 101 games in the NHL and had just 33 total goals (less than half of what Vanek had scored at the same point in their careers).

The offer infuriated Burke and resulted in him publicly blasting Lowe in the media the next day.

Along with calling the contract “gutless,” Burke also added that “Edmonton has offered a mostly inflated salary for a player, and I think it’s an act of desperation for a general manager who is fighting to keep his job.”

The feud between the two executives reached a point to where Burke wanted to rent a barn in Lake Placid so they could physically fight.

The Ducks refused to match the offer and in return received the Oilers’ first, second, and third round draft picks the following year.

From there, a lot of things happened.

  • The first-round pick Anaheim received ended up being the No. 12 pick in the draft. Anaheim then traded that pick for the No. 17 and 28 picks in 2008. They then used the No. 17 pick to select Jake Gardiner, who would eventually be traded to the Toronto Maple Leafs (along with Joffrey Lupul) in exchange for Francois Beauchemin.  The No. 28 pick was traded for two second-round picks.
  • The second-round pick Anaheim received from Edmonton was used to select Justin Schultz, who ended up never signing with the Ducks and once he became a free agent signed with … the Edmonton Oilers.

Penner was mostly okay with the Oilers, but probably wasn’t worth the assets they gave up to get him.

Flyers go all in for Shea Weber

Ah, yes, the Paul Holmgren era Philadelphia Flyers.

If there was a blockbuster to be made this team was going to do it. One year after overhauling his entire roster by trading Mike Richards and Jeff Carter so he could throw a bank vault at Ilya Bryzgalov, Paul Holmgren made what was perhaps his boldest move yet when he signed defenseman Shea Weber to a massive 14-year offer sheet that was worth $110 million.

[Related: Paul Holmgren’s year of crazy Flyers blockbusters]

The Predators were pretty vulnerable at the time because this was the same summer they had lost Ryan Suter in free agency to the Minnesota Wild, which came just a couple of years after losing Dan Hamhuis. The team was built around its defense and two of its three most important players were already gone. Losing Weber at that time would have been absolutely crushing.

The Predators decided to pass at the opportunity to collect four first-round draft picks from the Flyers and matched the offer.

They eventually traded Weber to the Montreal Canadiens for P.K. Subban, and then traded Subban this summer to the Devils for … well … a lot of salary cap space.

Scott Stevens had an extensive — and important — history with offer sheets

One of the first significant offer sheets came when the St. Louis Blues signed Scott Stevens to a four-year, $5.1 million contract to pry him away from the Washington Capitals on July 16, 1990.

The Capitals declined to match the offer and ultimately received five first-round draft picks in return, with two of them turning into Sergei Gonchar and Brendan Witt, two players that would go on to be long-time staples on the Capitals’ blue line.

Stevens would only play one season with the Blues before he was on the move again in the summer of 1991 in one of the more controversial rulings in league history.

It was then that the Blues signed restricted free agent Brendan Shanahan away from the New Jersey Devils. Because the Blues were sending all of their first-round picks to the Capitals for signing Stevens, they had to agree to other compensation to get Shanahan. There was a disagreement on what that compensation should be.

The Blues offered goalie Curtis Joseph, forward Rod Brind’Amour, and two draft picks.

The Devils wanted Stevens.

An arbitrator decided that Stevens was the appropriate compensation and awarded him to the Devils in a decision that infuriated the Blues and other high-profile players around the league, including The Great One.

Blues superstar Brett Hull was not as calm or measured in his statements.

And more…

Wild times.

This was during a CBA fight between the players and league with the players trying to get greater free agent rights. So it is not hard to understand why the Blues (and other players around the league) were so angry about it.

Stevens initially refused to report to Devils camp. He eventually did and would go on to become one of the most important players in franchise history and was the backbone of three Stanley Cup winning teams.

But his RFA saga would not end with this.

In the summer of 1994 the Blues had attempted to re-acquire Stevens, again a restricted free agent, and signed him to a four-year, $17 million offer sheet.

The Devils would ultimately match it, but were convinced the Blues had tampered with Stevens and spoke to him before his Devils contract expired. The league then launched an investigation and NEARLY FIVE YEARS finally reached a settlement that would see the Blues send $1.4 million and a first-round draft pick to the Devils as compensation for tampering.

Then-Devils general manager Lou Lamoriello was not satisfied with that resulted and wanted more.

Via the New York Times:

”I don’t look at something of this nature as a triumph,” Lamoriello said yesterday in a conference call after Commissioner Gary Bettman handed down his decision. ”It’s a detriment to the N.H.L. I don’t think the compensation could be severe enough. My request was five first-round picks, plus damages.”

And…

”In a process of negotiations, when they are ongoing and you are speaking, you can usually sense when there is something else involved,” Lamoriello said. ”I sensed that I was talking to myself. I just felt as though there was something funny in the way things transpired, the way things went. I was the sole person that could be negotiating, but I felt very strongly reading some of the articles that did come out of St. Louis and things I was hearing, that something happened. Where there was some smoke, I wanted to make sure there wasn’t any fire.”

Rangers try for Joe Sakic

In the summer of 1997 the New York Rangers were coming off of a conference Finals loss to the Philadelphia Flyers and had just lost their captain, Mark Messier, in free agency to the Vancouver Canucks.

Their response: To sign Joe Sakic, at the time one of the league’s best players, to a three-year, $21 million contract that had as much as $15 million in signing bonuses up front. The compensation would have been five first-round draft picks.

The Avalanche refused to let their cornerstone player get away and matched the offer. They would go on to remain one of the league’s powers and would win another Stanley Cup with Sakic in 2001. The Rangers, meanwhile, stumbled through a seven-year run of mediocrity where they attempted to acquire every aging superstar in the league. Nothing worked and the team was consistently an expensive flop until finally returning to the playoffs during the 2005-06 season.

For more stories from the PHT Time Machine, click here.

Adam Gretz is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @AGretz.

WATCH LIVE: Blackhawks face off against Predators on NBCSN

NBCSN’s coverage of the 2018-19 NHL season continues with the Wednesday Night Hockey matchup between the Chicago Blackhawks and Nashville Predators. Coverage begins at 7 p.m. ET on NBCSN. You can watch the game online and on the NBC Sports app by clicking here.

After a losing six straight games (0-5-1) in December, Nashville has rebounded with a five-game point streak (4-0-1) since New Year’s Eve. Their latest win was an impressive 4-0 victory over the Maple Leafs in Toronto on Monday. Rinne had 18 saves in his third shutout of the season.

Filip Forsberg returned to the lineup on Monday after missing 17 games with an upper-body injury. The team was 8-7-2 without him. Monday was Nashville’s first game since Nov. 10 with Forsberg, Viktor Arvidsson, and P.K. Subban all in the lineup.

The Blackhawks have climbed out of the basement of the NHL by going 7-4-2 since mid- December, but still have several teams to leapfrog if they want to make the playoffs. Still, they have become a tough out, as evidenced by their 4-3 loss to the Conference-leading Flames on Monday.

Patrick Kane has been red hot with 19 points (9G, 10A) in his last 11 games. He also has had multi-point games in four of his last six games. Jonathan Toews had a six-game point streak snapped on Monday, but still has 39 points (17G, 22A) in 45 games overall. Toews is on pace for 71 points and 30 goals, which would be his most productive season since 2010-11.

[WATCH LIVE – COVERAGE BEGINS AT 7 P.M. ET – NBCSN]

What: Nashville Predators at Chicago Blackhawks
Where: United Center
When: Wednesday, Jan. 9, 7 p.m. ET
TV: NBCSN
Live stream: You can watch the Predators-Blackhawks stream on NBC Sports’ live stream page and the NBC Sports app.

[P.K. Subban sends inspirational message to young fan after racist taunts]

PROJECTED LINEUPS

BLACKHAWKS
Alex DeBrincat – Jonathan Toews – Dominik Kahun
Artem AnisimovDylan Strome – Patrick Kane
Brandon SaadDavid Kampf – Drake Caggiula
John HaydenMarcus KrugerBrendan Perlini

Duncan KeithErik Gustafsson
Carl DahlstromConnor Murphy
Brandon Davidson – Henri Jokiharju

Starting goalie: Collin Delia

PREDATORS
Filip Forsberg – Ryan Johansen – Viktor Arvidsson
Kevin FialaColton SissonsCraig Smith
Calle JarnkrokNick BoninoAustin Watson
Ryan HartmanFrederick GaudreauRocco Grimaldi

Roman JosiRyan Ellis
P.K. Subban- Mattias Ekholm
Matt IrwinDan Hamhuis

Starting goalie: Pekka Rinne

Six-time Emmy Award-winner Mike ‘Doc’ Emrick, U.S. Hockey Hall of Fame member Eddie Olczyk, and ‘Inside-the-Glass’ analyst Pierre McGuire will have the call from United Center. Kathryn Tappen hosts NHL Live alongside analysts Mike Milbury and Keith Jones, as well as NHL insider Bob McKenzie.

MORE: Blackhawks’ Alex DeBrincat can’t stop scoring

WATCH LIVE: Predators visit Blackhawks on NBCSN

NBCSN’s coverage of the 2018-19 NHL season continues with Tuesday night’s matchup between the Nashville Predators and Chicago Blackhawks with coverage beginning at 7:30 p.m. ET. You can watch the game online and on the NBC Sports app by clicking here.

This is the second of four meetings between these Central Division foes. The Predators beat the Blackhawks 5-2 on Dec. 1 in Nashville. Pekka Rinne made 19 saves and five different Predators scored a goal.

During the 2016-17 season, the Blackhawks finished as the top team in the Western Conference with 109 points and faced the upstart Predators (94 points) in the First Round of the playoffs. Since Nashville delivered a surprising sweep in that series, the Preds have become one of the premiere franchises in the NHL, while the Hawks have taken a nosedive:

Last night in Ottawa, the Preds went down 3-0 in the first period and pulled Rinne, rallied back to force overtime, but fell 4-3 on Thomas Chabot’s OT winner. They have now lost seven straight on the road (0-5-2) after starting the season 8-0-0 away from Bridgestone Arena.

The Blackhawks snapped an eight-game losing streak last week with a 6-3 win over Pittsburgh, but have since lost each of their last two games — a 4-3 OT loss to Winnipeg on Friday and a 7-3 defeat on Sunday to San Jose. They have won just four times in their past 25 games (4-17-4) and are 4-13-3 under Jeremy Colliton.

Entering last week’s game against the Penguins, the Blackhawks had allowed the first goal of the game in 11 straight. Since then, they’ve tallied the first goal in two of their last three games. Chicago actually jumped out to a 2-0 lead against the Sharks and led 3-2 after the first period. But San Jose scored five unanswered goals from there.

When they do score the first goal of the game, Chicago is 8-2-4. When they allow the first goal of the game, they are 2-17-2.

[WATCH LIVE – COVERAGE BEGINS AT 7:30 P.M. ET – NBCSN]

What: Nashville Predators at Chicago Blackhawks
Where: United Center
When: Tuesday, Dec. 18, 7:30 p.m. ET
TV: NBCSN
Live stream: You can watch the Predators-Blackhawks stream on NBC Sports’ live stream page and the NBC Sports app.

PROJECTED LINEUPS

PREDATORS
Ryan HartmanRyan JohansenKevin Fiala
Calle JarnkrokKyle TurrisCraig Smith
Colton SissonsNick BoninoAustin Watson
Miikka SalomakiFrederick Gaudreau – Rocco Grimaldi

Roman JosiRyan Ellis
Dan HamhuisMattias Ekholm
Matt IrwinYannick Weber

Starting goalie: Pekka Rinne

BLACKHAWKS
Brandon SaadJonathan ToewsDominik Kahun
Dylan StromeArtem AnisimovPatrick Kane
Alex DeBrincatDavid Kampf – Dylan Sikura
John HaydenMarcus KrugerBrendan Perlini

Duncan KeithErik Gustafsson
Gustav ForslingBrent Seabrook
Carl Dahlstrom – Connor Murphy

Starting goalie: Cam Ward

MORE: Your 2018-19 NHL on NBC TV schedule

PHT Time Machine: Paul Holmgren’s crazy year of Flyers blockbusters

Throughout the season we will be taking an occasional look back at some significant moments in NHL history. This is the PHT Time Machine. Today we look back at the Paul Holmgren’s busy year as Flyers general manager.

The Philadelphia Flyers, at least for now, are back in the hands of Paul Holmgren following Monday’s dismissal of general manager Ron Hextall. Until a more permanent solution is found — something Holmgren is hoping takes “weeks” and not “months” — that means he is the one in sitting in the general manager’s seat with his finger on the button when it comes to the roster.

This is exciting. This is very, very, very exciting. For purely selfish reasons I am hoping he just decides to keep the job for himself because it might mean the Flyers become interesting again.

Who doesn’t love a completely unpredictable team that could totally change directions at any moment?

When the Flyers made Monday’s announcement, Holmgren said in a statement the franchise and Hextall “no longer share the same philosophical approach concerning the direction of the team.”

During a press conference discussing the move on Tuesday, the team seemed to double down on that when Comcast-Spectacor chairman and CEO Dave Scott said the team was looking for someone that has a “bias for action” in its new general manager.

You do not really need to reach very far in all of this to come to the conclusion that upper management did not care for Hextall’s patient, methodical approach to handling the construction of the roster, especially when it was producing mediocre results year after year.

[Related: Hextall’s patience failed to move Flyers forward]

This brings us back to Paul Holmgren.

During his tenure as general manager there was not a more aggressive team in the league when it came to trades and blockbuster roster transactions. Everything was on the table, no player was untouchable, and you should have always been willing to expect the unexpected.

One of his first moves as Flyers general manager during the 2006-07 season was to trade Peter Forsberg to the Nashville Predators for Scottie Upshall, Ryan Parent, and a first-round draft pick. That offseason, not even six months later, he sent that first-round draft pick back to Nashville for pending free agents Kimmo Timonen and Scott Hartnell, and then promptly signed them both to long-term contracts.

A few years later he also traded Parent back to Nashville for the free agent rights to Dan Hamhuis, and upon realizing he would not be able to sign Hamhuis, traded him to Pittsburgh for a third-round draft pick.

In the summer of 2009 he pulled off the most impactful trade of his tenure when he acquired Hall of Fame defender Chris Pronger from the Anaheim Ducks, a move that would ultimately lead to a Stanley Cup Final appearance the next season.

But none of these transactions hold a candle to the madness that happened between June 23, 2011, and July 18, 2012.

That was when all hell broke loose in Philadelphia and this series of transactions took place.

Let’s try to break this down here because my goodness that is an entire career’s worth of blockbusters in one year.

Splitting Up The Core For Ilya Bryzgalov

In the summer of 2011 the Flyers were coming off of a second-round playoff loss to the Boston Bruins (a sweep) and still trying to answer the long-standing goaltending question that has hounded the organization for decades.

Despite the disappointment of that postseason defeat, and even with the unsettled goaltending questions, this was still a very successful franchise. They were just one year removed from a trip to the Stanley Cup Final, they had won another playoff round that season, and were simply beaten by a better team (one that would go on to win the Stanley Cup that year).

That was still not good enough, and in the eyes of the Flyers the one thing that was still holding them back was a franchise goalie.

So they tried to address it.

It all started on June 23, 2011, when Holmgren completely blew up his core of Mike Richards and Jeff Carter (both of whom were signed to mega-long-term contracts) and traded them within an hour of each other.

Richards was sent to the Los Angeles Kings for Wayne Simmonds and Brayden Schenn, while Carter went to the Columbus Blue Jackets for Jakub Voracek and two draft picks, one of which would be used to select Sean Couturier.

At the time speculation was raised in Philadelphia that the “partying” lifestyles of Richards and Carter off the ice prompted the trades, speculation that Holmgren immediately wrote off as “preposterous.”

Really, though, it was probably just about not settling for anything less than a championship and doing whatever it took to land the goalie they thought would get them one.

That is where Ilya Bryzgalov comes in.

The trades of Richards and Carter coincided with the acquisition of Bryzgalov from the Arizona Coyotes. Upon acquiring his free agent rights the Flyers made him the highest paid goalie in the league — and by extension the new face of the franchise — by giving him a nine-year, $51 million contract.

These moves turned out to be a mixed bag that for a short period of time completely altered the balance of power in the NHL.

First, for as bold as the Richards and Carter trades seemed to be at the time the Flyers did end up getting great value in return as Simmonds, Voracek, and Couturier are all still outstanding players for them today.

Bryzgalov was also a really good goalie at the time and was coming off two outstanding years with the Coyotes where he finished in the top-six in the Vezina voting each year, including one year where he was the runner up.

Once he arrived in Philadelphia, though, his game almost immediately collapsed on itself resulting in a buyout just two years in to the massive contract.

Following that buyout he would only play 40 more games in the NHL.

The real gut-punch here for the Flyers isn’t just that Bryzgalov failed to fix the goalie situation, it’s that he failed to fix the goalie situation while Carter and Richards were ultimately reunited in Los Angeles later in the 2011-12 season (Columbus traded Carter for defenseman Jack Johnson) and won the first of their two Stanley Cups together.

The other gut-punch, in hindsight, is that one year after signing Bryzgalov they traded his backup, Sergei Bobrovsky, to the Blue Jackets for three draft picks.

All Bobrovsky has done since then is win two Vezina Trophies in Columbus and become one of the best goalies in the league.

It was a wild year.

The James van Riemsdyk saga

Just a little more than a month after trading Richards and Carter to make room for Bryzgalov, the Flyers made another huge move that summer by signing James van Riemsdyk to a long-term contract extension that, in theory, made him a significant part of their core going forward.

That contract was set to kick in at the start of the 2012-13 season.

He would never play a game in Philadelphia on that contract.

Following the 2011-12 season (which was another second-round exit) the Flyers traded him to the Toronto Maple Leafs in a one-for-one swap for defenseman Luke Schenn.

If we’re being honest here, this trade seemed like a bad idea from the start and it would never get any better as van Riemsdyk would eventually go on to become a top-line goal-scorer for the Maple Leafs.

Schenn’s contract became one of the albatross deals in Philadelphia that Hextall would have to jettison early in his tenure as part of his initial organizational clean-up.

What’s amazing about this series of transactions is that van Riemsdyk’s exit from Philadelphia was nearly identical to Carter’s. Just like van Riemsdyk, Carter had signed a long-term contract to remain with the Flyers only to be traded just months before it was set to start.

Bringing van Riemsdyk back to Philadelphia in free agency this past summer was one of Hextall’s last moves in charge of the Flyers.

The Shea Weber Offer Sheet

Every summer we look at the list of restricted free agents and like to pretend one of them might actually sign an offer sheet. It almost never happens. In the salary cap era only eight players have actually signed an offer sheet, and all but one was matched (the Anaheim Ducks did not match Edmonton’s contract for Dustin Penner).

The most notable of the offer sheets that did get signed was Philadelphia’s decision to go after Shea Weber on July 18, 2012, signing him to a gargantuan 14-year, $110 million contract.

This was a delicate time for the Predators because they had just lost Ryan Suter in free agency to the Minnesota Wild, and losing Weber would have been a crippling blow to the franchise. So they matched it, setting off an incredible chain of events in the years that followed.

Had the Predators not matched it, they would not have P.K. Subban today (Weber was traded for Subban a few years later).

They also may have never traded Seth Jones for Ryan Johansen because they would not have had the depth on the blue line to pull it off.  As a result, they may not have been a Stanley Cup Final team or a Presidents’ Trophy team the past two years.

It also may have left the Flyers, and not the Canadiens, as the team that is left trying to deal with the remaining years of Weber’s contract today.

And none of this takes into account what Columbus would look like today if it didn’t get involved in all of this.

In the end that is a lot of “what ifs” and is nothing more than a fun discussion. But it just added to the unpredictable madness that was the Paul Holmgren era in Philadelphia.

Did any of it make the Flyers any better? Tough to say because some of the moves worked out great, while some of them failed spectacularly.

They were certainly a far more interesting team thanks in large part to a general manager that had an extreme “bias for action.”

MORE: Your 2018-19 NHL on NBC TV schedule

Adam Gretz is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @AGretz.