The Pittsburgh Penguins, an extremely successful and popular NHL franchise that has seemingly had hockey’s top stars every year since 1984, aren’t used to selling anything at the trade deadline other than Stanley Cup playoff tickets.

Unfortunately, the 2023/2024 season has been one of reckoning for the Penguins. After narrowly missing the playoffs for the first time in 17 years a season ago, Pittsburgh is currently eight points out of a postseason spot with mere weeks left in the regular season.

Such a reality forced the Penguins to be sellers at this year’s deadline. Who was their top sellee? Jake Guentzel, Pittsburgh’s popular first-line winger, the man with 219 career goals and 466 points.

Guentzel made his NHL debut for the Penguins during the 2016/2017 campaign and helped them complete the second half of their run as back-to-back Stanley Cup champions. Guentzel was especially prolific in his first postseason in 2017, scoring 21 points in 25 games–including 13 goals. Guentzel, who played alongside Sidney Crosby for most of his career, scored 58 points in 58 postseason games for Pittsburgh.

Guentzel was one of the few players who knew how to vibe with Crosby, one of the greatest superstars the NHL has ever seen.

That all being said, Guentzel, like every other high-performing player, wanted to be paid a handsome contract. Full of expensive veteran superstars–including Crosby, Evgeni Malkin and Kris Letang–the Penguins were a bit hamstrung when it came to working out a new deal with Guentzel.

The 2023/2024 campaign would be Guentzel’s final one before becoming a free agent. He reportedly wanted a long-term contract approaching $9 million a year. A bit too rich for the salary-cap challenged Penguins. Trading Guentzel away at the deadline was the only option after it became obvious that, one, the two sides weren’t going to reach a new deal and, two, the Penguins clearly weren’t a Cup contender.

Guentzel quickly became the biggest asset on the market. What would Pittsburgh fetch for him? What would the bounty be?

Turns out, not as bountiful as Penguins fans–a crew that first made “Let’s trade our worst players for their best” famous–had hoped for. The Penguins traded Guentzel to the Carolina Hurricanes on Thursday in exchange for a veteran player, Michael Bunting; three prospects–including Ville Koivunen, Vasily Ponomarev and Cruz Lucius; and a conditional second-round draft pick that could turn into a first if Carolina makes it to the Stanley Cup Final.

That seems like a lot of quanity and lot a ton of quality. None of the three prospects were even in Carolina’s top five. As for Bunting, 28? He’s a slightly younger and less prolific version of Guentzel, who will turn 30 in October.

Why wasn’t there more of a return? Because Guentzel was a rental. First of all, no team that is contending for a title is going to give up a major asset from its NHL roster at the deadline; that would be stupid. Second of all, no team is going to give up its top prospect for a rent-a-player, especially when that player is closing in on 30 and has also expressed a desire to test free agency in the summer.

The time to trade Guentzel for maximum value would have been anytime before his free agent year. Even this past offseason would have been better. It would have given suitors a chance to work out a long-term contract with Guentzel as part of any trade.

Instead, Kyle Dubas, the team’s new president and general manager, orchestrated a trade for Erik Karlsson, the prolific offensive/defenseman, over the summer.

The idea was to give the Penguins, the oldest team in the NHL, one more chance at a championship. The core of Crosby, Malkin and Letang, who all have no-trade and no-movement clauses as part of their deals, wasn’t going anywhere. Therefore, Dubas had to continue to worry about the present and not the future.

The plan didn’t work. The Karlsson deal didn’t make the Penguins better. It just made it harder to blow the whole thing up and rebuild. Guentzel was the only moveable asset of great value, and Pittsburgh got all that it could for him.

Dubas recently said that the Penguins, an organization bereft of prospects due to many years of trying to acquire assets in order to win Cups, had to get much younger. The Guentzel trade helps to supply the farm system with some youthful prospects.

Are they great prospects? No, but Pittsburgh couldn’t even get a decent return for Jaromir Jagr back in 2001, and he just had his No. 68 jersey retired a few weeks ago.

Rent-a-players never seem to fetch the kind of return that everyone thinks they will prior to the deadline.

Again, after trading so many prospects and draft choices away in the name of winning Cups, after deciding to bring back Malkin and Letang two years ago, and after doubling down on the “now” by acquiring Karlsson last offseason, the Penguins have effectively painted themselves into a corner.

They can’t really move on from their core, and they don’t have the talent in the minors to replenish their NHL roster with the types of players who can make that core “younger” and faster.

The Penguins are in purgatory at the moment. They’re not really good enough to contend, but they also don’t have the ability to blow the whole thing up.

They can blow part of it up, however, and that all started with the trading of Jake Guentzel in exchange for youth and quantity.