Alex Pietrangelo, Toronto Maple Leafs?
Photo: @StLouisBlues

In today’s Leafs Links, the insiders discuss the contract structure Alex Pietrangelo is seeking on his new deal, the possibility of a rights trade before the October 9th free agency period, and the King City native’s level of interest in a homecoming to Toronto.

Leafs Links

Andy Strickland: The idea of being a Leaf 100% excites Pietrangelo (First Up)
Long-time Blues beat reporter Andy Strickland shared his understanding of how the negotiations ended up stalling between the Blues and Alex Pietrangelo, as well as his feel for Pietrangelo’s interest in coming home to Toronto.

I’ve always said from the beginning that this was going to come down to how the deal is structured. If you look at the St. Louis Blues in the past and how they structure deals, the organizational philosophy is that they have never, ever signed a player to a contract that includes signing bonus money. They’ve inherited contracts that have carried signing bonus money — and you can go back and forth on whether there is a difference between inheriting it versus negotiating it — and I’ve always believed it was going to be a hangup and potentially even lead us to where we are now.

Then you get into the no-move clause. I think a lot of people are focused on that. In talking to people with the Blues, they are signing this is negotiable. I don’t think it is completely off the table in the minds of the Blues, but for whatever reason they haven’t put it on the table. That is something Alex Pietrangelo is going to want.

When you look at the course of his career here — being the captain, winning a Stanley Cup, being an elite player for several years — a no-move clause seems like it would be relatively easy to negotiate. Obviously, he would love to have that towards the backend of the contract. We always talk about front-loading money — and it is important in this situation — but it is also having that protection towards the backend of the contract. When you have that no-move clause, you can’t be bought out. You can’t predict how your career is going to go in those latter years of the contract, so these players want that protection.

The Blues say it is negotiable. Whether we get back to that point and if the two sides truly negotiate before we get to UFA, it seems a little bit slim, but until he signs on the dotted line elsewhere, he remains a Blue. We’ll see what happens.

Strickland on the current emotions being felt on both sides of the negotiation:

I sense a lot of frustration. There is frustration on the player’s part because he feels he has done everything he can do at this stage of his career and he should what he is asking for.

On the flip side, for the Blues, there is some frustration that there has maybe been a little bit of negotiation going on through the media. We all know Doug Armstrong doesn’t like that. He doesn’t negotiate through the media.

We are still a couple of weeks out until October 9th, so this is a little early for me to see the emotions get to the level of where they are at right now. Typically, you see that as you get closer to the dead-end date. With still a couple of weeks left, typically, a lot can happen and a lot can turn over that time frame.

In this situation, as much as Pietrangelo wants to stay in St. Louis… There is a lot of focus on his wife being from here, and maybe he would be willing to take less in order to stay here. Maybe he would in terms of the AAV, and what I understand the Blues have put on the table is in the neighbourhood of 8×8. Whether they are willing to go north of that remains to be seen. It may be more than he gets on the open market, and I think Pietrangelo’s camp even understands that. If he gets $9 million on a seven-year deal, obviously, $64 million is higher than 63. I don’t think it truly comes down to the money. It comes down to how the deal is structured.

At the end of the day, I truly believe the idea of going elsewhere and entering free agency excites Pietrangelo. I think he is excited to see what else is out there. He looks at the window to win with other franchises and compares that to St. Louis — maybe he sees some teams out there that will have interest in him and where the window may be a little more open than in St. Louis.

As much as he wants to stay, I do think Pietrangelo would be interested in moving to another franchise where he thinks the long-term ability to win might be greater than what he is seeing in St. Louis right now.

Strickland on the report that the Blues told Pietrangelo to go test UFA:

I think that was more a mutual decision. There may be some misinformation that is out there. We may not have full clarity until the full process is over. But the idea that the Blues just threw their hands up and said, “You go into FA. We are moving on.” I think both sides understand they’re both not getting what they want. Both sides are expressing the same thing: If we are not getting what we want, we might as well take it into free agency and see if he can get what he wants in free agency.

It was mischaracterized a little bit with the team saying, “We’re done. You go to free agency.” Collectively and mutually, both sides agree with that.

Strickland on whether signing in Toronto excites Pietrangelo:

I think it 100% does… Alex Pietrangelo probably has a picture somewhere of sleeping with Toronto Maple Leaf pyjamas, or some Leafs posters hanging on this wall. I think that 100% exists. Now, whether or not they can meet those demands… Toronto is going to competing with other teams as well to get his services.

You look at the signing bonus money the Leafs have paid Marner and Matthews — the Blues don’t need to pay that type of bonus money. He is not looking at that type of signing bonus money from a team like St. Louis. But from a team like Toronto, knowing they can afford to pay that? They are going to have to in that range similar to what we are seeing with Matthews or Marner. It might not be that high, but it is going to be significantly higher than what we are seeing in St. Louis.

Does it excite him to potentially play in Toronto, understanding what the career earnings could mean even after you’re done playing, and the possibility of bringing home a Stanley Cup to his hometown in the first time in well over 50 years? That 100% excites him, and I can’t blame him for that.

LeBrun: Major upgrade on blueline the Leafs’ urgent, #1 priority (Overdrive)
Pierre LeBrun provided his latest intel on the Alex Pietrangelo front, including his feel on whether we could see a rights trade in advance of the UFA window opening. LeBrun points out that Kyle Dubas and the Leafs would’ve put one together in order to acquire John Tavares in 2018, but Lou Lamoriello was not interested.

This isn’t just about money when it comes to the breakdown in these talks. The Blues just don’t give out signing-bonus money. Brayden Schenn signed a gigantic deal last year and zero signing bonus went in that eight-year deal that he signed. Ditto for Justin Faulk, who signed a seven-year extension a year ago when he joined the Blues. 7×6.5 with no signing bonus money.

Alex Pietrangelo is not those guys. He is their captain. This has been contentious and frustrating from Pietrangelo’s point of view. He gave a pretty heartfelt interview with Jeremy Rutherford in The Athletic on Friday night. I interviewed him a week before and I could sense the frustration creeping into his voice. The frustration is that he probably feels he should’ve been taken care of a year ago after they won the Cup. It didn’t happen.

The interesting thing in all of this: If you sit back and look at St. Louis and Boston — the two teams that have managed their caps, I think, better than any other organization in the NHL over the past few years — they have some interesting moments this offseason with Torey Krug and Alex Pietrangelo potentially going to market. Those teams are not used to losing core players. They’ve had guys buy in and sign for less and play for less. They’ve run into a couple of headstrong young men who understand the business. The Bruins with Krug and the Blues with Pietrangelo — they are not just taking their agents’ advice but are quite invested in the situation, they have done their homework, and they believe in what they believe in.

LeBrun on the Leafs‘ level of interest:

It goes without saying that if Pietrangelo is on the market October 9th, the Leafs are going to be among the teams that are going to absolutely find out what it’s going to take. That doesn’t mean they’ll get him. I don’t know if the Leafs can afford to get him at any price. But they will inquire, as they should.

When I talk to other teams around the league, I have had the message from other teams that what they hear from the Leafs all the time in the last month: “We need a real upgrade on our blue line. That is priority #1.” We’ve been talking about that for a few years, but the point is, I think there is some urgency to it that we maybe haven’t seen before.

That doesn’t mean it has to be Alex Pietrangelo. To me, he would be the ideal candidate, even with all of the cap issues it creates, because he is just the kind of game changer that you just don’t see often available as a free agent. On the right side for the Leafs, playing on the top pair with Morgan Rielly, would just be an insane upgrade for the Toronto Maple Leafs.

It would force some changes up front that are difficult — no question. You’d have to entertain potentially trading Nylander or trying to package two or three other forwards who frankly don’t have that much value in the market. Andreas Johnsson has been hanging around the market for a while now.

This is how hard it is for teams to move money: I talked to a GM who told me, “It is next to impossible to move money right now.” You’ve got NHL owners telling their GMs, “We are not adding to the payroll.” It is really a crazy market right now in terms of trying to move money.

If the Leafs can’t make a move to sign Pietrangelo, whether it’s signing a Chris Tanev or a trade for Matt Dumba, they need to augment their top four if not their top two. That is their number one priority. It is not just a media-driven thing. It is what the Leafs are trying to do.

LeBrun on the possibility of a rights trade for Pietrangelo:

It is an absolute fact that had Lou Lamoriello been open to this, the Leafs would’ve done a sign-and-trade for Tavares, which would’ve gotten them the eighth-year on Tavares. Where I am going with this: If Pietrangelo does go to market — and there still is absolutely a chance the Blues make another offer, who knows what happens — everyone always thinks the eighth year matters more to the player than anyone else, but it might actually matter more to the Leafs or any other team. It would bring down the AAV. The idea of tacking on an extra year to massage the money — it would’ve happened with Tavares. He would’ve come in at a slightly lower AAV had they made a trade with the Islanders. Lou Lamoriello had no interest in it at the time, and you get why.

If the Blues make another effort to sign him and strike out again, do they get someone who wants that eighth year, and what do the Blues get out of it? And what does the team that is going to sign Pietrangelo get out of it? It would be to bring down the AAV.

We haven’t seen it often. Had Stamkos walked on Tampa back in 2016, I am told it is something Tampa looked into, and I think it was San Jose. Had he signed with San Jose, it might’ve been a sign-and-trade to bring down the AAV. That is something else to keep in mind on this. It is sort of another layer.

Cam Janssen: Still think Pietro signs in St. Louis (First Up)
Blues broadcaster Cam Janssen predicts the two sides will circle back around and find enough common ground to keep Pietrangelo in St. Louis.

I think, in the end, Pietro is going to sign in St. Louis. I really do. I think he is going to give it a little bit, and that’s kind of what you do. If you want to go to the free market, you know you are going to get paid and the structure you want. You know that already. It is going to last a couple more weeks here, and then [the’ll get it done].

Dreger: Structure of the deal crucial for Pietrangelo  (Leafs Lunch)
Darren Dreger confirmed Andy Strickland and Pierre LeBrun’s earlier reports that the structure of the deal and Doug Armstrong’s no-signing-bonus philosophy has been a sticking point in St. Louis. He also argues a core piece will need to be moved to accommodate the Pietrangelo cap hit in Toronto.

Toronto is almost desperately looking for a top-pairing right-shot defenseman. We know that there is going to be one available in UFA. Now, the St. Louis Blues may wait until October 8th and Doug Armstrong volleys another offer at Pietrangelo that puts pressure on Alex and his family to make an 11th-hour decision, but that is not an expectation at this point.

if you are the Toronto Maple Leafs, I can’t get the pencil out and figure out how the Leafs make it work, but I would say this: If Pietrangelo is on the market on October 9th, the Leafs are going to make an offer. What that offer looks like, what the AAV has to be — I don’t know — but I know structure, above all else, is crucial to a deal getting done with Alex Pietrangelo.

The St. Louis Blues aren’t a big-market organization, so cash flow matters. When you are talking about signing bonus money, that is a tough one for the St. Louis Blues to manage. They just don’t have the wherewithal to do it, but I can appreciate Pietrangelo or any high-end UFA putting a real importance on the structure and the signing bonus money that can be incorporated into a deal.

When we are talking about what the Leafs are looking for, they are looking for a top-pairing right-shot defenseman. The reality of the situation is the only way they get that is by diving into the market if Pietrangelo is available. How else are you acquiring that piece? How else? Those guys aren’t available. They’re just not available.

Dreger on the cap situation in Toronto:

Andreas Johnsson getting traded for a draft pick isn’t enough… The Leafs have 18 players under contract at $6.1 million in cap space [with Mikheyev and Dermott to sign]. That is fine, but you are going to chew all of that and then some and some if you are going to sign Pietrangelo. How are you acquiring that piece if you aren’t moving out a core player just from a cap perspective?

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