Exploring some different paths the Penguins could take this offseason to improve

The 2023 Stanley Cup Playoffs are taking place and the Pittsburgh Penguins are not involved. This is relatively uncharted territory for the organization based on the past couple of decades, and the new general manager — whoever they end up being — is going to have quite a mess to clean up after Ron Hextall and his staff left behind this broken roster.

The good news is the Penguins still have Sidney Crosby, Evgeni Malkin, and Kris Letang as their core, and they are not only still all still great, they are also signed to below market contracts.

As the Boston Bruins and Los Angeles Kings have showed us this season, it is possible to still build a highly competitive team around a core of veterans in their mid-to-late 30s. You just need to have a front office with a plan that knows how to complement them.

As far as developing a plan to do that, the new front office will have some constraints and hurdles to deal with.

The first is the fact the Penguins have a thin cupboard of prospects to deal from as it is is basically Owen Pickering and then a whole bunch of nothing.

The second is the unrestricted free agent is about as bad as it has ever been in terms of impactful talent. To be fair, this is usually the case because teams tend to keep the good players and the free agent pool is usually relegated to a bunch of guys that already played their best hockey for somebody else and weren’t deemed worthy of keeping by that somebody else.

It is almost always a fool’s paradise that requires careful maneuvering. But this year it seems even worse, especially as it relates to defensemen and goalies. It’s just a bunch of guys waiting to be overpaid and bought out two years from now.

I was going to suggest this would be a great year for the Penguins to explore an offer sheet (yeah, I know, they almost never happen and almost never work), but they no longer own their third-round pick which really limits what they can do there and takes them out of the running for offers they could make for truly impactful talents.

Where did that third-round pick go, you ask? Traded with Brock McGinn to dump his bad contract and to acquire Dmitry Kulikov,

Great asset management, Ron.

All of that is frustrating because the Penguins actually do have some salary cap flexibility, even after the idiotic trade for Mikael Granlund. Even with Granlund they still have a little more than $20 million in salary cap space with 14 players under contract. They could clear up an extra $4 million this offseason by buying out Granlund.

If you really wanted to get wild you could clear out $3.2 million this year with a Jeff Petry buyout (they are not going to do this, and I am not even sure they should, but it is just a hypothetical option).

In other words, they have some salary cap flexibility and could easily give themselves a lot more.

So with all of that said, what can a new general manager realistically do here?

Some options.

1. Give up on competing and start the rebuild

There are a lot of people that would like to see this be the chosen path, but I am not among them. Like I said above, they still have a core you can win with and there are enough examples of how it is possible out there.

I also am not even sure how you actually DO that.

The players that you would trade as part of a rebuild have no-trade clauses they are not likely to waive, and it probably would not work out as planned anyway. I do not get the desire to become bad and unwatchable faster.

As long as you still have a realistic path to compete and be a playoff team, you should explore that path and try to do it.

Especially when you still have a trio of Hall of Famers that are still playing like top-line stars (while being signed below market value).

This is a no from me. Especially when you actually have some really salary cap space for the first time in a long time.

2. Use your draft pick capital as trade assets

There is only one scenario in which I would not want to actively trade the Penguins’ first-round pick this year.

And that is if they by some chance win the draft lottery and pick in the top-five.

At that point, you might actually land an impact talent that could meaningfully impact your future.

But if that pick is 14th or 15th?

Put that thing on the block and do not think twice about it. At that point you are talking abouot a 50/50 chance at an NHL regular, maybe a 10 percent chance at a star, and a very strong likelihood of getting the next Kasperi Kapanen or Samuel Poulin. It has more short-term and long-term value to you as a trade asset than an actual draft pick at this point.

I would also go further than and consider future picks, either as a trade, or the offer-sheet route if you can find somebody that is vulnerable to that and would not require your own 2024 third-round pick.

Target potential RFA’s this summer on cap-strapped teams. Alex DeBrincat in Ottawa. K’Andre Miller in New York. Evan Bouchard in Edmonton. Jeremy Swayman in Boston.

Get aggressive.

Even if the Penguins are not a top team next season they are unlikely to finish in a spot where that future first-round pick is going to be a top lottery pick or a franchise-altering talent. Almost nobody in the 15-25 spot is changing your future rebuild unless you get wildly lucky and fortunate.

If that pick is outside of the top-five, aggressively try to trade that thing. Do not hesitate.

3. Make a pure hockey trade

What exactly does that look like? Well, somebody significant. The easy answer is Jake Guentzel. He has one year left on his current contract, is going to be in line for a HUGE payday beyond that, and he will be 30 years old when that next contract begins. There is some risk there with that.

In recent years I would have been — and have been — a million percent opposed to the idea of shopping Guentzel. Even now I am not saying they should. But hypothetically speaking, what if you could swap him for a top-tier defensive player? Not a trade for prospects or picks. But somebody that could immediately step in right now as a high-level player at another position? Even somebody in a similar contract situation to upgrade another area of your roster? Would you trade him for, say, Devon Toews? I am not suggesting that is something that would be realistic on the table, but just as a rough idea for the sort of return I would want to see to make it worth it.

Guentzel is the easy option for a hockey trade proposal because he is one of the few players on the roster that actually has some trade value that is not Crosby, Malkin, or Letang. Maybe Bryan Rust fits that category. Maybe Marcus Pettersson. Maybe Rickard Rakell.

Those are the four options for such a deal.

There are probably going to be some potential unrestricted free agent options that could be good values. They are still worth exploring, especially when it comes to building out your forward depth. But free agency is not likely to solve the goaltending situation. Or reshaping the defense in a meaningful way. Or finding a top-nine scorer that could give the Crosby and Malkin lines the complementary offensive support they need. Options two and three are the only realistic ways to achieve those goals.