Photo Credit: Jeff Curry-USA TODAY Sports

Should the Leafs explore a sign-and-trade for Alex Pietrangelo?

Welcome to Pietrangeloctober

If you haven’t heard, there’s a top-pairing right-handed defenceman with Stanley Cup-winning pedigree from just north of Toronto who seems destined to hit the open market 15 days from now. His name is Alex Pietrangelo, and he’s a wanted man around these parts. Make no mistakes about it, Leafs GM Kyle Dubas is going to pursue this player hard once free agency opens on October 9th.

…or maybe he’ll pay to skip the line?

Pierre LeBrun of the The Athletic laid out the conditions under which the Blues could extract an asset in exchange for a player they may lose for nothing two weeks from now, whilst simultaneously helping interested but cash-strapped teams like Toronto or Vegas to fit Pietrangelo into their cap situation.

The concept is simple: there is only one team that can sign Alex Pietrangelo to an 8-year deal: the St. Louis Blues. The Blues, however, are drawing a hard line on giving Pietrangelo no movement protection and a bonus structure that would make his contract virtually buy-out proof towards its end. These two contract conditions are of no concern to the deep-pocketed Leafs, who would gladly give Pietrangelo those protections just to bring him into the fold.

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So, an arrangement would need to be made: the Blues could act as an intermediary between Pietrangelo and the Leafs, by signing him to an 8-year deal of the Leafs’ design and immediately trading him to Toronto. The Leafs would then send an asset the Blues’ way for brokering this deal. A sign-and-trade.

The Leafs have actually pursued a sign-and-trade at least once before during Kyle Dubas’ reign: the John Tavares sweepstakes. Just two summers ago the Leafs explored the idea with the Islanders when it felt like Tavares was leaning towards his hometown team. From the sound of things, time simply ran out before the deal could come to fruition, with Tavares making his decision the night before free agency began.

The main difference here is that the Islanders desperately wanted Tavares to stay. There was no ultimatum, no animosity, no disagreement on contract structure and no advisement on part of the Isles for Tavares to pursue free agency. The Isles were in the running until the dying moments of June 2018, and a sign-and-trade was far from their minds.

With this situation, it feels different. While it’s entirely possible Pietrangelo will re-sign with the Blues and this full-press media tour is nothing more than posturing, the general sense from hockey insiders is that this may not just be an act. Pietrangelo could conceivably be a member of a different team in two weeks from now. St. Louis probably would be amenable to getting something for their captain instead of being left with nothing more than great memories.

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So what will it cost?

The Leafs will need to balance the acquisition cost against the benefits of tacking on an eighth year to bring down Pietrangelo’s average annual value. From LeBrun’s reporting, he suggests the Blues would likely ask for a first round pick for their troubles but that it was unlikely a team would meet that asking price. Could a second round pick or a young player with upside get it done?

Assuming the 15th overall pick is off the table, the Leafs do have their own 2nd round pick (44th overall) to part with. In terms of roster players who could be of interest to the Blues, a player like Travis Dermott sticks out as someone they may ask about. With Morgan Rielly and Jake Muzzin locking down the top two slots on the left side of the Leafs’ defence, Dermott is currently in the way of Rasmus Sandin getting meaningful minutes at the NHL level. This would help alleviate some of that logjam, and while losing Dermott would hurt, the Leafs have the depth at LD to compensate. And they’d end up with Alex freaking Pietrangelo.

There’s also Andreas Johnsson who keeps getting dangled in every trade proposal this summer, but the aging Blues may prioritize injecting some youth into their blue line in response to Pietrangelo’s departure. This would, however, be a dream scenario as the Leafs would only be adding roughly $5M in net new salary expense with that swap.

Or let’s get absolutely wild: what if the Blues retained salary on the sign-and-trade? That may be what gets them the first rounder they covet, whether it be from the Leafs or Golden Knights or mystery team who swoops in at the last minute.

Should the Leafs explore this option?

My repeated proclamations about roster construction aside, the reality of the situation is the Leafs have an unofficial contention window of four more years, coinciding with the end of Auston Matthews’ current deal. After then, who knows what is going to happen? John Tavares isn’t getting any younger. The cap is flat. The planet is dying. Maybe we just go for it?

Assuming the acquisition cost isn’t too high, the Leafs should absolutely investigate any avenue which results in them being able to lower Pietrangelo’s AAV. With how top heavy the team is currently built and the tough realities of the league’s financial situation, every penny saved on this deal is tremendously valuable.

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Whatever happens, it’s shaping up to be a very suspenseful next two weeks. The sign-and-trade dream dies with the opening of free agency on October 9th, so Kyle Dubas and company should soon be reaching out to Blues GM Doug Armstrong, if they haven’t already.

Buckle up, Leafs fans.