Penguins still battling Father...

We’re about a month away from NHL prospect camps, and training camps will start a week after that. But before things begin, summer was interrupted by a blockbuster trade and a few notable signings.

Penguins hoping to fend off Father Time

The Pittsburgh Penguins were a fascinating team even before they acquired Erik Karlsson. They started and finished last season as the oldest team in the league, en route to missing the playoffs by just one point, acquiescing the final spot to the Florida Panthers.

Pittsburgh did have a minus-2 goal differential compared to the Panthers plus-17 mark (the lowest goal differential among all playoff teams), but at the same time, they were fourth in 5v5 expected goals (them and the Flames were the only two top-10 teams to not make the playoffs), and ninth in 5v5 corsi.

Sidney Crosby had another big year with 93 points in 82 games, Evgeni Malkin had 83 points in 82 games and Jake Guentzel had 36 goals and 73 points in 78 games. Their top players were generally productive and their 5v5 stats similarly reflected well, but with the season on the line, they played .500 hockey from March 1 onwards, going 10-10-2 with some crushing losses — including a home loss to the Chicago Blackhawks and a blown lead against the New York Islanders.

The Penguins looked old and worn down during the stretch drive, ultimately fizzling out before the playoffs even began. Now, after the Karlsson trade, they once again project to be the oldest team in the league. They have nine forwards, all of whom should be in their starting lineup on opening night, plus four more defensemen all on the wrong side of 30. Between 1976-2020, the Stanley Cup winner's average age was 27.21. Vegas went into this past Stanley Cup playoffs with an average age of 28.1. Colorado won with an average age of 26.5 while Tampa Bay won with average ages of 27.1 and 27.3.

In fact, no team this millennium has won a Stanley Cup with an average age over 30 (though the 2001-2002 Detroit Red Wings were at 29.9 in fairness), and that’s seemingly where the Penguins are going to end up. Trying to win with a team this old is unprecedented, but the Penguins have a number of generational, unprecedented players trying to do it. All of Crosby, Malkin, Karlsson, as well as Kris Letang, remain very productive in the late stages of their careers and will no doubt flash greatness next season. But can they do so night after night in a grinding 82-game season, let alone in the playoffs every other night for two months after that?

Moving Karlsson a tough but necessary pill

On the one hand, considering Karlsson is the reigning Norris Trophy winner and just had a 101-point season, receiving a top-10 protected first-round pick and three veterans likely to be flipped for draft picks does not sound like much of a return for the San Jose Sharks.

On the other hand, however, clearing Karlsson’s contract, which has four years remaining at an annual cap hit of $11.5 million, is still immensely valuable to the Sharks. Even coming off the great season he had, it’s difficult to imagine Karlsson making that much money per season were he a free agent this summer. With a stagnant salary cap that has remained flat for multiple seasons now, the highest annual average salary given out this summer was $7.75 million to Dmitry Orlov, a number that is itself inflated given he signed for just two seasons.

It was also no secret that Karlsson was being made available, and yet he did not have many suitors and his contract is a big reason why. San Jose needed to cash in on the 33-year-old's career season and wound up retaining a relatively minuscule $1.5 million AAV, clearing $10 million per year for the next four seasons. That significant chunk of cap relief — and flexibility that comes with it — ultimately serves as the true value of the Karlsson return for a player whose value couldn’t possibly be higher.

So, should they have retained more to encourage a bidding war and up the return? The Sharks are also retaining $2.7 million in each of the next two seasons from the Brent Burns trade and have cap penalties for buyouts of Martin Jones' and Rudolfs Balcers' contracts. At some point, Sharks GM Mike Grier needed to stop the bleeding, and you have to clear the books so to speak to start anew.

The Sharks are already on the hook for nearly $7.5 million in dead money this upcoming season, just under $6 million the season after that and over $3 million in the following two seasons. They'll have to navigate the cap wisely in order for this to work, and they will need to eventually get some value back when they eventually trade the veterans acquired in this deal. It’s not a trade that is going to get fans excited — and it actively took the most exciting player on their team off of it — but it’s a move that should set the table for the Sharks in the years to come.

Montreal a sneaky winner in Karlsson sweepstakes

It’s not often you see a three-way trade where a broker comes in and doesn’t retain any money. In the Karlsson trade from San Jose to Pittsburgh, however, the Montreal Canadiens did just that.

For their purposes, all Montreal really did was move money around and open up a roster spot at forward by trading Mike Hoffman and Rem Pitlick, while acquiring Jeff Petry, Casey DeSmith and a second-round draft selection. The Canadiens then flipped Petry to Detroit for defenseman Gustav Lindstrom and a conditional 2025 fourth-round pick. Since 2020, there have been 11 three-way trades (excluding this one), and all but one were because a team retained money to help flip a player to their final destination. The only three-team deal that didn't have a third team help shuffle money was a straight three-player trade involving Michael Del Zotto, Giovani Smith and Danny O’Regan moving for each other.

The Habs evidently saw an opportunity, however, and moved players and contracts around to their advantage. Even after trading away two forwards, the Canadiens have at minimum 14 forwards vying for playing time. Usually, that would mean that said team finds itself in a squeeze and lacking leverage, but given the seismic trade, Montreal managed to slide in and avoid compromising its position.

Instead, the Canadiens acquired a veteran goalie in DeSmith, a second-round pick, plus the return they got from Detroit for Petry. Every extra pick helps in a rebuild, whether to infuse young talent into a burgeoning pipeline — Montreal has drafted 20 players over the past two drafts and owns 20 picks over the two upcoming drafts — or to add young established NHLers like Kirby Dach or Alex Newhook.

Just how good can Troy Terry be?

The salary cap is largely designed to keep salaries in check and to even the playing field for teams across the league to compete. As such, the best way for teams to take full advantage in a cap system designed to promote parity is to draft, develop and sign quality players to below-market-value deals, allowing for teams to allocate that extra money elsewhere to deepen their roster.

It's a tried and true method that every successful team has taken advantage of. Matthew Tkachuk is already underpaid at $9.5 million. Nathan MacKinnon won a Cup making $6.3 million per season. Jack Hughes found another level right after signing for $8 million per season. David Pastrnak just scored 61 goals making under $6.7 million. And each of these deals were signed as restricted free agents.

The Anaheim Ducks are hoping to become the league's next big benefactor. While Trevor Zegras remains unsigned as an RFA, the Ducks have already locked up former world juniors star Troy Terry to a six-year, $42-million contract. Anaheim won’t be the first team to bet early on its top players, but it has had virtually no success prior to doing so.

Over the past three seasons, the Ducks have the worst points percentage in the league with a record of 103-153-35. Their goal differential in that time is an equally putrid minus-287. That isn't to say a turnaround isn't possible. The New Jersey Devils finished 28th in NHL during the 2021-22 season, then signed Hughes to a massive extension and made the playoffs the following year, even winning a series against their Hudson River rival New York Rangers in the process. All told, it’s not impossible.

For Terry, in particular, it’s noteworthy that he turns 26 in September. Similar comparables in terms of salary, including Kyle Connor and Matthew Boldy, were 22 when they signed their big extensions. Players closer to Terry's age, like Kings forward Kevin Fiala, had seen multiple productive seasons before inking a big extension. Jordan Kyrou, another player with a comparable trajectory to Terry, signed for more money, but had experienced some playoff success also and plays center.

Terry, contrastingly, has truthfully had only two good seasons. During the 2021-22 campaign, the University of Denver product took off with a 16-game point streak — accumulating 22 points during that stretch — and finished the season with 37 goals and 67 points. This past season, Terry saw his production dip slightly, with 61 points in 70 games. His goal total also dropped to 23 as his shooting percentage plummeted from an unsustainable 19.3% to a far more reasonable 12.23%. With a rising cap, if Terry remains productive, he’ll likely be worth the money on offense alone. If the 25-year-old can take a step defensively and be a true top line player, however, it’ll be yet another steal of an RFA extension.

The importance of letting the frenzy settle

Last summer, the Dallas Stars reportedly offered defenseman John Klingberg an eight-year extension worth around $7 million per season, according to Jeff Marek. Klingberg, however, hoped to cash in closer to $8 million, causing negotiations to break down.

In free agency, the market for Klingberg cooled, eventually leading to a one-year, $7 million prove-it deal with the Ducks. From there, Klingberg and the Ducks each had disastrous seasons, as the Swedish blueliner was eventually traded to the Minnesota Wild to cap the weakest season of his NHL career to date. This past summer, Klingberg inked a one-year, $4.15 million deal, this time with the Toronto Maple Leafs.

Going into this summer, Tyler Bertuzzi and his agent were looking for term and security. When the market wasn’t presenting the offers he wanted, the gritty forward ended up signing a one-year deal, also with Toronto, for $5.5 million. Vladimir Tarasenko reportedly had offers in the $5.5-6 million range with varying degrees of term, but ended a lengthy free agency saga by signing a one-year, $5-million deal with the Ottawa Senators.

Players have bet on themselves before and hit the jackpot, but it can also swing the other way. Once the first few days of free agency pass, many teams have used up much of their available cap space or filled the holes on their roster. They simply can’t afford to meet the demands of players and, in the absence of that, players are forced to either take a discount long-term or take one-year "show me" deals. To that end, these signings aren't just a cautionary tale for players, but a potential market exploit for teams to take advantage of. Instead of running wild on Day 1, teams should try avoiding the free agent frenzy and let the market come to them, at a discount no less.