Jerry Lai/USA Today Sports

Since the Detroit Red Wings won their last Stanley Cup in 2008, many hockey fans have been wondering when a new dynasty could overtake a team that has been led by Scotty Bowman, Steve Yzerman and Nicklas Lidstrom for the last decade and a half. Considering the salary cap has in place for close to a decade, chances are that word would almost never apply again in the modern NHL. However, there has been one franchise that has been close to pulling it off and they have been so much fun to watch and to analyze. That team is the Chicago Blackhawks when they won their second Stanley Cup in four years in 2013.

A year later, the defending champs would lose to Los Angeles in overtime, capping off one of the greatest playoff series in recent NHL history and one of the greatest defenses of a Stanley Cup since that Detroit Red Wings team tried to repeat in 2009. If there’s one team the Blackhawks are not ashamed to lose to, it would be to a team that also has won two Stanley Cups in the Salary Cap era, but the Kings’ “core” is Drew Doughty, Jonathan Quick and a bunch of late-20s forwards who have found their perfect change of scenery via the trade market. Does that look like a strong contender for a dynasty? If things break right, perhaps, but not one that you would think would rival the 1980s Edmonton Oilers in NHL lure.

Chicago, on the other hand, is full of young players that were drafted and magically turn into 10-12 of what could either be the best in hockey or some of the best bargains while still not having hit their peak. When Chicago won their last title in 2013, they didn’t just have Jonathan Toews and Patrick Kane at 25 and 24, respectively. They had Brandon Saad at 20, Andrew Shaw and Nick Leddy at 21, Marcus Kruger at 22, Ben Smith at 24, Nicklas Hjalmarsson at 25 and Bryan Bickell at 26. The Brent Seabrook and Duncan Keith tandem were 27 and 29, respectively. The only aging players to worry about were a 31-year old Patrick Sharp and a 34-year-old Marian Hossa. However, Sharp would lead the team in scoring in 2014 and landed a spot on Canada’s Olympic roster while Hossa continues to be one of the most underrated hall-of-fame candidates of his generation. He is now five tallies away from hitting the 1,000-point mark in 1,090 career games.

What has made the Blackhawks so fun to watch was just how incredibly dominant they were on both ends of the rink during their two title runs. In 2010, they led the league in fenwick close percentage by a full 4.4%. Even more shocking was during that same year, Chicago finished second in fenwick-for-close per 60, but were best in fenwick-against-close per 60 by almost a full five shot attempts. That has been, by far, the biggest margin of victory in that category since puck possession has been recorded (since the 2007-08 season).

Their blue line might go down as one of the best assembled with not only Hjalmarsson, Seabrook and Keith on the roster, but a 30-year old Brian Campbell and a 24-year old Dustin Byfuglien were on there as well. Four of those guys would have 30-point seasons and Campbell and Byfuglien would go on to become the most recognizable names on their current team’s defensemen group. In their forward ranks, Andrew Ladd, Kris Versteeg and Troy Brouwer were also on the roster and younger than 25. All three of them would go on to play top-six minutes for other teams, with Andrew Ladd being selected captain of the Winnipeg Jets.

However, Chicago’s chance of repeating could have come to an end after the team was looking everywhere for cap space. In the summer of 2009, General Manager Dale Tallon came under immense scrutiny by not tendering the offers to Adam Berti, Adam Pineault and Logan Stephenson while signing Marian Hossa, Tomas Kopecky and John Madden for a combined 2010 cap hit of $9.225 million. Martin Havlat’s $6 million contract was off their books, but Brian Campbell was in the second year of an 8-year deal that gave him a cap hit of a little over $7.1 million. At the time the deal was signed, only Zdeno Chara and Nicklas Lidstrom had a bigger cap hit amongst defenseman and it is still the fifth highest cap hit among blue liners today. The exclamation marks to the whole problem were that Hossa signed for a 12-year deal, while Duncan Keith was resigned to a 13-year deal. With all these acts in poor cap management and the fact that Tallon decided to fire Denis Savard as head coach four games into the 2008-09 season, it was decided from Blackhawks management to demote Tallon and replace him with Stan Bowman, the son of the head coach who’s last team he coached for the Blackhawks were trying to emulate.

It took another four years for the Blackhawks to return to their dominant selves and it wasn’t like 2010 all over again. Los Angeles were the defending champions coming into the 2012-13 season and they lead the league in puck possession that year. But with injuries to several key players, Chicago lucked out in their conference final matchup with the Kings and the Blackhawks were able to seal a Stanley Cup final appearance in five games and then another Stanley Cup with a six-game series win over Boston. Their journey came by gradually freeing up their cap space in trading for Michael Frolik and Viktor Stalberg in 2010, trading away Brian Campbell for future cap casualty Rostislav Olesz and flipped Tomas Kopecky for another cap casualty in Steve Montador in 2011 and then trading for Johnny Oduya in 2012.

What’s been incredible during their reload, was that since Patrick Kane was drafted in 2007, only the Red Wings (don’t you love the symmetry?) have had less than the 75 career NHL games the Blackhawks’ first round picks have played. However, Bowman and company have absolutely lucked out in drafting Ben Smith in the 6th round in 2008, Marcus Kruger in the 5th round in 2009 and Brandon Saad in the 2nd round and Andrew Shaw in the 6th round in 2011. Along with having their mainstays continue to develop, the recipes for another Stanley Cup were in the works. The rewards of that process turned front office assistants Marc Bergevin and Kevin Cheveldayoff into General Managers for Montreal and Winnipeg respectively.

On July 9th of this year, Jonathan Toews and Patrick Kane, the two people solely responsible to bringing hockey back to relevancy to Chicago, resigned before their current contracts are up at the end of this upcoming season by both receiving the eight-year max deal. That was no surprise, considering their status as among the best in hockey, but seeing that their yearly cap hits would hit $10.5 million certainly was a surprise. These extensions resulted in the Blackhawks to be more than $2 million over the cap coming into the season. All this occurred despite signing Brad Richards and David Rundblad in the off-season. The scarier part of that, is that none of them were worth more than one-year of term or $2 million in cap-hit salary. Without any players that are eligible for season-long LTIR (hello, Chris Pronger, Marc Savard and Mattias Ohlund!), Chicago will be the only team that has to make a trade in order to go below the salary cap before the upcoming regular season.

Viktor Stalberg, Dave Bolland and Michael Frolik had to leave Chicago after their 2013 Cup run and even though Stalberg has been struggling with Nashville and Bolland just couldn’t stay healthy for Toronto, Frolik has been one of Winnipeg’s best penalty killers. Even though he is 37 years old, Chicago will lose another shorthanded specialist in Michal Handzus. The Blackhawks have enough experienced reinforcements there with Marcus Kruger, Marian Hossa, Jonathan Toews and Ben Smith, but head coach Joel Quenneville likes to use as many forwards as possible on the kill. Last year was the first year the Hawks have employed less than six forwards that have either played more than half the season or were pickups at the trade deadline to more than a minute of shorthanded time on ice per game.

When Chicago’s core group of players goes away, some will state that the beginning of the end were the Toews and Kane extensions, but what we’ve learned from the Capitals are that the beginning of the end starts from somewhere you least expect and as it continues to linger and that is what eventually rots the entirety of your team. The first signs of rotten contracts could still be from that summer of 2009 as Marian Hossa, despite showing no signs of age, is now hitting his late 30s. We have seen with Johan Franzen how a player hitting his stride so late into his career can crumble so fast. Duncan Keith might be one of the five best defenseman of his generation, but his cap hit of a little over $5.5 million will continue until he is 39 years old. Chicago was rewarded in the short term with the 2010 Stanley Cup and they were very fortunate that Toews and Kane resigned for a combined $12.6 million per year for five years after their rookie contracts were over that season. Now, those two just signed their infamous third contracts, usually the one that dishes out the most money and term to the player that has entered the prime of his career.

The $10.5 million extensions not only put a microscope on Toews and Kane, but it will make Blackhawks fans question even further contracts given to other players on the team that don’t deserve them. The two biggest examples are the ones given to Bryan Bickell and Corey Crawford after winning the cup in 2013. Bickell has truly had a weird career despite playing on one of the best teams of the modern era. While only putting up 15 goals, 31 points and 3.3 point shares per 82 games with 12.1% shooting, 12:22 time on ice and 2.44 shots per 20 minutes in the regular season, those numbers change to 29 goals and 49 points per 82 games with 17.2% shooting, 15:28 time on ice and 2.64 shots per 20 minutes in 57 career playoff games. Things like that make people like Steve Simmonds and Don Cherry drool and make NHL front offices decide that a 4-year, $16 million contract was worth it for Bickell. Sadly, that is about $1.5 million too much for a guy that took until his age-24 season to play regularly in the NHL and doesn’t consistently play top six minutes during the big sample size that is the regular season.

For Crawford, his 2013 season saw him save 92.6% of his shots while averaging .204 point shares per game. His previous two seasons as Chicago’s starting goaltender were below league-average with point shares per game numbers of .179 and .136, respectively. Last year, that number was below the consistent league-average .18 mark again at .173. That simply doesn’t justify giving someone like Crawford a contract extension of six years and $36 million. The only goalies that have signed for more money and longer term without tons of media scrutiny were Carey Price, Henrik Lundquist and Tuukka Rask and all of them were either the most consistent or best goalies in the league or signed their contracts at a time where they haven’t hit their peak yet. Crawford is turning 30 in December and has another five years left and a cap hit that ties him with Ryan Miller as the sixth most among goaltenders.

Down in the farm, the small amount of talent brought in from the first round could begin to haunt Chicago, even though 2012 pick Teuvo Teravainen is expected to be in the lineup this year. That leaves players like Nick Schmaltz, Mark McNeil, Philip Danault, Stephen Johns, Jeremy Morin, Ryan Hartman and Adam Clendening to be counted on to develop really soon. Speculation has it that someone in the Michal Roszival, Nick Leddy and Johnny Oduya triumvirate (all three on the last year of their contracts) could be traded in order to go below the cap, but that puts all the pressure on Rundblad, Johns and Clendening to be counted upon playing top-four pairing minutes during the regular season and another cup run. Once this season is over, Roszval, Oduya and Brad Richards become unrestricted free agents and Leddy, Marcus Kruger and Brandon Saad will be given contract extensions well beyond the $2.7 million, $1.35 million and $764,167 they are given, respectively. Stan Bowman was fortunate beyond belief to get someone like Brad Richards in the off-season to make them favorites to win the Cup 2015. But with the money being thrown around free agents that give any positive contribution to a hockey team and the still uncertain chances the Salary cap will increase significantly in the long term, it is looking more like now or never for this memorable group of players and this window could close sooner before anyone expects it.