In 2017, the Pittsburgh Penguins clinched their second consecutive Stanley Cup, the first NHL team to win back-to-back championships in the salary-cap era. Franchise stars Sidney Crosby, Evgeni Malkin, Kris Letang, Marc-Andre Fleury and Chris Kunitz, who came up short six straight seasons after making back-to-back Finals appearances in 2008 and 2009 (lost to Detroit in ’08, beat Detroit in ’09), had created another chapter in their careers.
It was because the franchise had finally found the core to assemble around them.
General manager Jim Rutherford during the 2015 season acquired long-time Toronto winger Phil Kessel in a blockbuster trade that sent multiple draft picks and players. He also would snag center Nick Bonino, defensemen Trevor Daley and Justin Schultz and speedster Carl Hagelin, all of whom would play large roles during the Pens’ next two trophy tours.
Patric Hornqvist was a pest in front of the net, Matt Cullen was a veteran presence on the fourth line and Ben Lovejoy and Ian Cole both played valuable minutes on the back end.
However, perhaps the most important pieces were the developed talent: Conor Sheary, Bryan Rust, Jake Guentzel, Scott Wilson, Tom Kuhnhackl, Brian Dumoulin, Olli Maatta and goaltender Matt Murray. It was what had been missing from the organization for some time.
When the Pens had made their back-to-back Final runs in ’08 and ’09, it had been with homegrown talent: Brooks Orpik, Cup legend Max Talbot, Tyler Kennedy, Alex Goligoski, Jordan Staal and obviously, Crosby, Malkin, Letang and Fleury helped a little.
They had acquired talent that had been on the squad for many years in Craig Adams, Matt Cooke in the pest role. They had added pieces Pascal Dupuis, Petr Sykora, Ruslan Fedotenko, Miroslav Satan and big rig Hal Gill and further pursued at the deadline veteran Bill Guerin and Chris Kunitz before they won Lord Stanley.
You had to have all three: drafted, developed talent, an evaluating sense for offseason acquisitions and a buyer’s eye for detail and skill at the trade deadline.
During 2016-2017, the Pittsburgh Penguins had that. The highs of those two years were very high but for every high, there is a low.
The low was right around the corner.
The Slide Begins
Sunday, April 22nd, 2018, the Pens would clinch a playoff series win over the Flyers 4-2.
They have not won a playoff series since.
They would lose to the rival Capitals in the second round but Rutherford, always the reactionary, had made his first cataclysmic mistake nearly a full year earlier.
Following the Penguins’ second championship, Rutherford had decided too many liberties had been taken by opponents with his star players, specifically by the league’s most famous goon, Washington Capital Tom Wilson. Rutherford wanted to trade for brawler Ryan Reaves, whose most marketable skill had been fighting.
This went against head coach Mike Sullivan’s team mantra “Just Play” and against the entire philosophy of the team’s roster construction. The Penguins’ last two Stanley Cup squads had been built on speed and a high-pressure attack. Reaves had neither of these traits but Rutherford, so overcome by rage, traded a first-round pick and winger Oskar Sundqvist, one of the team’s top up-and-coming young talents.
Rutherford’s reputation had always been as a gambler and someone who preferred buying players to drafting them. This has never been a good plan to build a hockey team or a sports organization for that matter but because Rutherford had walked into an organization that had not one, not two, not three but four Hall-of-Famers at the peak of their careers and a pool of drafted, developed and ready-to-go prospects, Rutherford’s early hits on Kessel, Daley, Hagelin, Bonino and Schultz afforded him a lot of rope he had not earned.
Reaves would play 58 games for the Penguins, see little ice time and record eight points before Rutherford dumped him to Vegas and sent defenseman Ian Cole, a first-round pick, a third-round pick and Filip Gustavsson, the team’s top goalie prospect, to Ottawa for Derick Brassard. Brassard would register 33 points in 54 games before Rutherford moved him and multiple draft picks for forwards Nick Bjugstad and Jared McCann.
Marc-Andre Fleury, the longtime franchise goaltender, was selected by the Vegas Golden Knights after the emergence of goaltender Matt Murray during the two championship runs. He’s continued to be one of the best net protectors in hockey, driving Vegas to a Stanley Cup final in their first year, winning a Vezina as the league’s top goalie his last year in Vegas and now playing quality hockey for Minnesota.
Scott Wilson, a developed bottom-six forward prospect from the Cup team, was dealt away in October.
During that 2018 season, Rutherford would slowly but aggressively begin dismantling the small dynasty the Pens had, shipping Sheary, Hagelin and Maatta by July of 2019, preferring size and grit over the speed that had won them so many games, including trading for Jack Johnson and Erik Gudbranson, two of the worst defenseman in hockey according to multiple analytical models and signing the former to a gargantuan five-year contract. After two almost impossibly bad years of performance, the Penguins bought out Johnson’s contract.
The Penguins are still paying Jack Johnson to not play hockey for them in 2023 and won’t finish doing so until spring 2026.
Cup champions Carter Rowney and Kuhnhackl would find themselves out of Pittsburgh that offseason.
The Decline Speeds Up
In his final years, Rutherford would continue pushing buttons, shipping out more key contributors, prospects and picks such as Phil Kessel, Patric Hornqvist and top defenseman prospect Calen Addison, who he threw out for Jason Zucker, a routinely injured winger on a heavy contract.
Rutherford would also continue his habit of trying to correct earlier mistakes. Gudbranson, who had become a black hole on defense, was moved as well as recently-acquired Bjugstad. The returns, Alex Galchenyuk and Patrick Marleau, would flop in Pittsburgh.
He’d then trade yet another first-round pick for former Pens draft choice Kasperi Kapanen, who he had previously shipped off for Kessel. Kapanen was the worst player on the roster during most of his second stint in Pittsburgh before once again being moved this past offseason.
Rutherford during his final year with the team would continue throwing grit at the ice, signing bottom-six forward Brandon Tanev to a titanic six-year contract in free agency. Tanev would be moved two years later because of said contract.
The Hextall Era
Trading Fleury and keeping Murray ended up blowing up in the Penguins’ face. Murray’s play wavered from inconsistent to minor-league level and Rutherford shipped him to Ottawa. Luckily for Rutherford, another ready-to-go goalie prospect he wasn’t responsible for was there to clean up his mess in Tristan Jarry, who he immediately extended.
It was an extremely odd part to Rutherford’s tenure. Whenever he acquired a player, he’d sign them to a long-term, often highly-priced extension but a player rarely ever played out a contract with the Penguins. Pittsburgh had become a conveyor belt of hockey players, more like a luggage rail at an airport than a hockey team.
Then, Rutherford abruptly quit for “personal reasons.”
While unsubstantiated, there is a rumor it was because Rutherford wanted to trade Letang and owner Mario Lemieux stepped in and said no. Whether that specific rumor is true or not, it seems fair to conclude ownership wanted his gambling reigned back and Rutherford was unwilling to oblige.
Last additions to the team via Rutherford were Mike Matheson, a defenseman who couldn’t figure out defense in Pittsburgh and winger Evan Rodrigues.
While the largest cancer in the organization was finally removed, there was plenty of his leftover garbage remaining on the team and payroll and tasked with removing it was Ron Hextall, a former Flyers goalie and general manager who had gotten run out of Philadelphia because of his vanilla, indecisive approach.
However, if Rutherford was the all-too-ambitious pawn mover, Hextall, at least by reputation, was the general manager who hated to do anything. It should, in theory, be the exact opposite of JR.
For the second time in three years, Pittsburgh would lose to a less talented New York Islanders team in the first round of the playoffs. Isles coach Barry Trotz’ defense-first, responsible approach was a perfect foil to Sullivan’s attacking style and the Pens’ more talented roster found themselves fundamentally outplayed for the third consecutive season.
Jarry would struggle severely in the series with New York and much of the blame for yet another organizational setback, rightly or wrongly, was sent to him by the media, fans and franchise.
Hextall’s Hex
Unfortunately for Penguins fans, Hextall brought the same philosophy to roster construction to the Penguins as Rutherford had. The reason the Pens weren’t winning wasn’t because of a lack of speed, creativity and youthful energy. It was because the team “wasn’t tough enough.” Right after moving Tanev, a bruiser with an obese contract, Hextall one week later replaced him with Brock McGinn on a four-year, a bruiser with a now fat contract. McGinn was traded less than two years later.
The one move Hextall made at the previous deadline was Jeff Carter, a 36-year-old vet who performed extremely well after being acquired, scoring nine goals in 14 games and five points in six playoff games.
The following season, Carter would play well as a third-line center, amassing nearly 50 points in 76 games.
Hextall extended him to a two-year, which seemed highly risky given age is more than a number in sports. He was 37.
Hextall also included a no-trade clause, which was very unusual for a player of Carter’s age and situation. The hope was Carter could continue as a third-line center.
That decision has proven to be a disaster. Last season, Carter struggled in every spot on the lineup. Now in 2023, Carter is playing fourth-line wing.
Winger Jared McCann, acquired in one of Rutherford’s numerous trades, would be moved. Last season, McCann had 40 goals and 70 points for the new Seattle Kraken.
Hextall would also perform a Rutherford impression and take a swing at the deadline, trading for Rickard Rakell. After 13 points in 21 games in a black and gold sweater, Hextall threw a six-year, $30 million contract at him, the exact type of thing Rutherford used to do.
Pittsburgh would blow a 3-1 series lead to the New York Rangers that postseason, cementing four straight seasons without a playoff series win. It was time to blow it up.
Keep Digging
It was time to let it go. The championship window was closed.
Letang and Malkin were free agents. Letang had just had a phenomenal season and was still top-five at his position. Pittsburgh brought him back with a six-year contract to lessen the cap hit but the final two years will likely be paying a player to stay home in retirement.
As much as I love Malkin, he had a penchant for injuries during his career. He had failed to play 70 games each of the last four seasons. I thought the right move was to let him go and inject youth into the roster.
It came down to the wire, with Malkin threatening free agency but the Pens chose to keep him.
This was not a terrible move but that meant all the more pressure to bring young faces into the building. They could not turn this into a retirement tour, seasons of nostalgia and “remember when we were good six years ago?”
But that’s exactly what happened.
One of Rutherford’s final moves was extending talented, young prospect John Marino after one strong season to a six-year contract, a term so obnoxious Hextall was forced to move him in the 2022 offseason, as in one year after the signing, to get the numbers off the books. If you recalled, Pittsburgh had to do the same with Hornqvist because Rutherford thought money grew on trees. Marino is now a key cog on an emerging New Jersey Devils team while the Pens try to patch together a defense.
At this point, it wasn’t even the cost that hurt the most about this move. It was the age.
By this point, Pittsburgh was fielding the oldest team in hockey and not just because Crosby, Malkin and Letang are all over 35. All of the youth and developed talent was shipped out or never realized because Rutherford had such a penchant for burning draft picks.
Hextall’s tenure would include Jeff Petry, Mikael Grandlund, Jan Rutta, Josh Archibald and 34-year-old Nick Bonino, who would walk off the plane and get injured immediately. He’d play three games in his second Pittsburgh stint.
Stuck in the Mud
While Letang dealt with a second stroke, Crosby and Malkin had phenomenal years. Both 87 and 71 played all 82 games and both averaged more than a point per game, finishing with 93 and 83 points respectively. The best-case scenario for those two happened.
Pittsburgh still missed the playoffs, ending the longest active playoff streak among the four major North American sports leagues at 16 years.
Needing two wins to clinch, the Pens’ final two games were against Chicago and Columbus, two of the worst teams in hockey. They lost both.
I love Bryan Rust but I hammered the table to let him walk in the summer of 2022. His best hockey was behind him. You would pay more for him than you ever have to do less. It wasn’t smart business.
Hextall did it anyway: six-years, $30.75 million.
Rust had his worst season in years in 2022.
The Carter situation has reached defcon 1. He finished a -16 plus-minus.
Prospect Teddy Blueger never developed an offensive skillset. He managed 10 points in 45 games before he was traded.
Jason Zucker had 27 goals but who Pittsburgh really needed from Minnesota was not Jason Zucker.
Sitting in Minnesota last season between the irons was former Pens top goalie prospect Filip Gustavsson, who Rutherford had traded years earlier in the failed Brassard trade. Gustavsson finished the year with a 2.10 goals against average and .931 save percentage, both marks among the very best in the NHL, trailing only Vezina winner Linus Ullmark.
The Penguins goaltending carousel finished the year with a 3.03 and .897. If only the Pens didn’t trade everything.
A False Prophet Enters
After five seasons of failure, surely now was the time for change. General manager Ron Hextall was fired and in came Toronto wonderboy Kyle Dubas. Dubas had been known in hockey circles as a young analytical mind and the media praise surrounding the hire was deafening. This was the man who would turn the team around.
Pittsburgh, who had just missed the playoffs after starting the oldest roster in hockey, had obvious problems: old players on pricey contracts, complete lack of youth and prospects and a stale coaching approach. Sullivan is still one of the league’s best coaches but it had become clear the aggressive, swarming, forecheck style was not agreeable to older legs. Sullivan had to adapt or move on.
Dubas, quite quickly, let everyone know how he felt about the team.
He traded for winger Reilly Smith.
Smith, fresh off a Stanley Cup championship with the Vegas Golden Knights, was 32 years old.
Sure, Smith had demonstrated he was capable of producing 50-60 points over the course of a season and production like that is nothing to shrug at but Reilly Smith is 32 years old and on a two-year contract at five million per year.
There comes a point in time where production simply no longer matters and when you’re the oldest team in the National Hockey League, that time is knocking on your door.
The Penguins, quite clearly, could not make this trade but the Penguins Retirement Tour must continue.
There’s a false confidence currently breathing on Fifth Avenue, a belief that this team, led by Crosby, Malkin and Letang, can win a Stanley Cup. After four straight first-round exits and a missed postseason, it has been voiced, loud and clear, they can’t. As I mentioned earlier, Crosby and Malkin had the best case scenario season, both registering point-per-game years and missing a combined zero games.
How much better do the Penguins believe they can play??
Five years is an eternity in sports. A lot about a sport changes in that time. There’s an influx of younger talent, an introduction of new statistical models to evaluate players and innovations to coaching.
The era of 2018 hockey is long gone and the players who excelled at it are now in the present. Continuing to proceed as is and refusing to adapt to the current environment is an inexcusable dereliction of duty.
The Penguins can choose to turn around at any time, to stop digging, accept their failed approaches and return to the basics of building a sports franchise but Dubas and the Fenway Sports Group backing him announced this summer they will continue to dig.
The Summer From Hell
The last player drafted by the Penguins to play more than six games for the organization coming into the 2023 season was Dominik Simon. Simon was drafted in 2015 which means the drafts of ’16, ’17 and likely ’18 you can throw in the trash. Those players aren’t coming to the NHL roster any time soon.
Given the franchise is still chucking high selections into the rivers, the drafts of ’19, ’20 and ’21 might also be sunk, meaning six straight failures at the draft.
The scouts and numbers minds who had helped build this team were ignored for one man to go on a shopping spree whenever he saw fit. Rutherford, in an almost ritualistic sense, sent out draft picks to the point I genuinely wondered why the Penguins had a scouting department.
Giving one person this much control of your organization is bound to go poorly and it has caused so much carnage in the finances of this team, it will take another five years for the last marks on the books to be wiped out. The quickest way to sink a team or a business for that matter is poor money management and Jim Rutherford was a master at it.
Hextall made additional mistakes and now Dubas, fresh on the scene, made sure to make his own skidmarks.
Sure, he got rid of Jeff Petry, Mikael Granlund and Jan Rutta, all Hextall decisions that had gone poorly but what did he replace them with?
The exact same thing.
The biggest problem with Petry, Granlund and Rutta were they were aged veterans and/or making too much money. This is before we even get to evaluating how they fit into the schematics of the team. Financially, it’s a no-go but the Penguins, stubborn to the last man, kept trying to slam square pegs into round holes.
Dubas replaced these players, all of whom were over the age of 30, with more players over the age of 30:
Noel Acciari, 31, two years, $6
Lars Eller, 34, two years, $5
Matt Nieto, 31, two years, $1.8
28-year-old defenseman Ryan Graves, who had never registered 30 points in a season? Six years, $27
All the financial trash Dubas cleared out was immediately replaced with more handcuffs because that’s what contracts are: handcuffs. The longer the deal, the tighter the restraint.
At 31, 34 and 31, it is highly statistically probable that Acciari, Eller and Nieto have played their best hockey. They are scientifically more likely to be injured and slower and when, as has been discussed, you have no young talent to replace them with because you sent out all those potential lottery tickets for players who didn’t work out, you are now an injury away from having an unproven player no one’s ever heard of starting for you for significant stretches of the season.
Not a recipe for success, ever, in the history of time.
During the last three seasons, Pens media and fans have been told by the team itself and by management that goaltending was an issue and actually, the main problem during their last two postseason exits. Goaltender Tristan Jarry, the initial salve to Rutherford’s Fleury debacle, has become a china doll. His health is seemingly always in question. It’s unfortunate because when available, Jarry has demonstrated top-ten potential and having a quality netminder is certainly an advantage but Jarry is 28, which means his peak is likely fast approaching. Given that, the postseason struggles and the continual injury bug, re-signing him was not an option.
Dubas signed him to five years and a penny under $27 million.
This means ownership, management and the franchise as a whole, doesn’t know what the problem with this team is. For months, years even, they’ve said, “Yes, the goaltending, the injuries, some pucks rolling the wrong way for us, it’s unfortunate. Those are ones we’ve got to have.”
During multiple trade deadlines and offseasons, they’ve had a chance to make a change. They claim they have a problem, do nothing about the problem and when they have a chance to let “the problem” go, they extend him.
Here’s the truth: Tristan Jarry isn’t the problem.
If he was the problem, he wouldn’t be wearing black and gold this offseason. No one wants to hear about, “Well, there weren’t better options available so we decided to just deal with what we have.” You’re a professional sports organization. Your job is to evaluate talent and better said talent. If you feel incapable of doing so, you’re in the wrong business.
Goaltender Cam Talbot is 36 and therefore, too old for this team. He’s also been an inconsistent journeyman during his career but the Los Angeles Kings, a defensively responsible team, have found success with him. Talbot currently sports a 2.02 goals-against average and a .931 save percentage, both top-five marks thus far. We’re a quarter into the 2023 season.
29-year-old netminder Joonas Korpisalo spotted a .913 in 28 games in 2022 with Columbus and a .921 with the Kings after the trade deadline. He signed with Ottawa for five years and $20 million, significantly less than Jarry.
28-year-old winger Tyler Bertuzzi was one of the biggest free agents available. He signed a one-year contract with Toronto for $5.5. Bertuzzi registered 62 points in 68 games for Detroit, nearly a point-per-game, during the 2021 season and this after registering two 20-goal, 45-point seasons in ’18 and ’19.
The previous offseason, 25-year-old Jakub Chychrun was traded to Ottawa for a first and two seconds. This would have been a heavy haul to pay but he has two years at $4.6 remaining on his contract and has registered over 35 points four times in his still young career.
Bertuzzi and Chychrun are both pieces that would be long-term additions, not short-term, “let’s squeeze out what little hockey is left in him” band-aids.
It is hard to find young talent in free agency but it’s not impossible.
Nail in the Coffin
Erik Karlsson. Future Hall-of-Famer, three-time Norris trophy winner as the league’s best defenseman.
Drafted by Ottawa all the way back in 2008, Karlsson was among the league’s faces for multiple years, with five straight 60-point seasons from 2013-2017.
In 2018, he was traded to the San Jose Sharks and in the summer of 2019, signed a contract that made him the highest-paid defenseman in league history: seven years, $92 million and an annual cap hit of $11.5.
The returns for the Sharks were disappointing. From 2018 when they traded for him up until last season, Karlsson didn’t break 60 games played or 50 points. When you’re the most expensive defenseman in hockey, you can’t just be good or even very good. You have to be great. Periods of injuries and inconsistent play hampered him.
Then, last season, Karlsson put up career-highs in goals (25), assists (76), and points (101), capturing his third best defenseman award.
A stunning season, one that deserved recognition and applause but this was not an asset you wanted to buy. Even the basics of stocks tell you to buy when the price is low, not when it’s just skyrocketed.
But the Penguins, ever the financial wizards, must have missed that lesson.
Dubas traded a 2024 first-round pick (wouldn’t want one of those), a second-round pick in 2025, the aforementioned Petry, Granlund and Rutta and backup tendy Casey DeSmith for Karlsson.
With this new, lovely $10 million yearly payment, Pittsburgh currently has 14 players under contract for 2024, as in half an NHL roster, accounting for nearly $68 million for next season, giving them roughly $20 million to form half their lineup card.
Karlsson, by himself, accounts for nearly 12% of the team’s payroll and makes nearly double what Kris Letang makes. Letang is every bit the player Karlsson is. The financial gap between the two demonstrates the value they get in Letang while showcasing the financial illiteracy of trading for a signing like Karlsson, the sixth-most expensive player in hockey.
Karlsson, by the way, is of course over the age of 30 at 33 and he’ll be on the books until he’s 37.
The Penguins strategy in 2023 is to establish the All-Star team of 2017. The immediate returns have been as expected.
To the Basement
The Penguins started the season 3-5, finishing with their first losing record in October since 2005 and sole possession of last place. Pittsburgh, the oldest team in hockey by over a full year, with an average age of nearly 31 years old, will be outskated against younger rosters all season. Especially come March, the wear and tear on their legs will show.
But, and you may be surprised to hear this, the wear and tear has already begun. Rickard Rakell, who I mentioned earlier, last season had his best year since 2017, scoring 28 goals and 60 points, dressing in all 82 games.
This season, he’s played 17 games and managed no goals and only four assists. This is the type of production you could get from Kasperi Kapanen, who was the team’s black hole last season. A friendly reminder Rakell has five years and $25 million remaining on his contract. He went on long-term injured reserve this week, meaning he will miss, at minimum, ten games. When he returns, a third of the season will be gone and he won’t have scored a goal yet.
Hextall’s deadline acquisition Jeff Carter has been so awful, he’s been a healthy scratch this season. He went 13 games before recording a point against Toronto on Saturday. He’s $3.125 against this season’s cap.
Bryan Rust was having a career resurgence, no doubt helped playing alongside Sid, netting 16 points in 17 games. He’s now injured.
Jake Guentzel, one of the few drafted and developed guys they have left, has 22 points. He’s a free agent after the year and thanks to the Karlsson trade as well as the rest of the Summer From Hell, this will likely be his last season in Pittsburgh. Guentzel has 35+ goals and 70+ points in each of the last two seasons.
During a six-game stretch this season, the Pens had 19 goals. 16 were by Crosby, Rust, Guentzel, Karlsson and Malkin.
When you surround your star players with aged veterans well past their expiration date, this is the result. Crosby is near the top of the league in even-strength goals and points and the team is still losing.
The team’s problems also didn’t just start this October. In their last 65 regular season games, per the Athletic’s Josh Yohe, the Penguins have won only 20 games in regulation. Per Penguins historian Bob Grove, they’ve lost 11 of their last 43 games when leading after two periods, including five times with multiple goal leads.
A big selling point of the Karlsson trade was that he would fix the team’s powerplay woes. We’re now a quarter into the season and the Penguins have the seventh-worst powerplay at 13.2%. It’s not just a personnel issue. It’s structure.
The Penguins are fourth in shots, meaning they’re put in positions to score. They’re scoring on 9.3% of those chances. That’s sixth-worst.
Last season, it was 9.3. The season before that, it was 9.4. In 2020, they led the league in shooting percentage at 11.5 and that is the last time this team was a serious contender.
The Penguins goaltending is sixth in goals-against-average at 2.63 and 4th in save percentage at .922. They’ve allowed only 50 goals, sixth-best. They have five shutouts in 17 games, only the fifth team since 1974 to do that.
It has been the case since the beginning of their playoff drought. It is not a coaching issue. Their analytics from Corsi For percentage to Expected-Goals-For (extremely stupid and flawed statistic but that’s a talk for another time. This is long enough.) are strong.
It is not a goaltending issue. Jarry’s injuries are an extreme annoyance but when he’s on his game, you’ll be hard-pressed to find a half dozen goalies better.
His contract is horrid and will come back to bite them like so many in the recent past (five years for someone with his medical chart is unwise) but his current play allows the team an opportunity to succeed.
They simply don’t execute their chances and the teams they play, with younger, blooming talent, do. Between that and an executive branch that both doesn’t understand the concepts of drafting and developing or how to manage a pocketbook, the Penguins are very much in a hole.
They will stay there until they stop digging. Enjoy the Retirement Tour.
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