The Toronto Maple Leafs Have a Massive Advantage in Free Agency

The Toronto Maple Leafs are expected to try and sign Alex Pietrangelo if he reaches free agency.

It looks like Alex Pietrangelo will be hitting the free-agent front on October 9th, and it’s still unclear where he’ll end up. As rumours swirl around the prospect of landing him, we will take a look at the advantage that the Toronto Maple Leafs possess over nearly every other team in the NHL.

As it’s been reported, the contract talks between the St. Louis Blues and Alex Pietrangelo have not gone according to plan, and with free agency shortly on the horizon, we look to what the prospect is that the Blues Captain signs with the Toronto Maple Leafs.

Over the weekend it seems as though St. Louis conveyed the message to Pietrangelo that it is in his best interest to test the free agency waters, thus making the chance of the Leafs signing him go up tenfold.

Toronto Maple Leafs Advantage

TSN reporter and Hockey Insider Darren Dreger (@DarrenDreger) also had this to say on TSN 1050’s Leaf Lunch Tuesday afternoon, “If Alex Pietrangelo is on the market on October 9th, the Toronto Maple Leafs are going to make an offer. Now what that offer looks like – what the AAV has to be, I don’t know. But I know that the structure [of the contract] above all else is crucial to a deal getting done with Alex Pietrangelo.”

If Pietrangelo (or any other big-name player) signs with the Leafs, the structure of the contract will be crucial. It would have to look like something similar to the way that the deals John Tavares, Auston Matthews, and Mitch Marner signed over the last couple of years. The structure of these deals paying players a boatload of money in signing bonuses upfront and over the first couple years – dwindling every year – and little to no money in actual salary.

The Advantage

$43.8 million of John Tavares $77 million contract will have been paid for over his first three years in Toronto (7-year contract). For Auston Matthews, it’s $42.27 million of $58.17 million that will be paid for over the first three years (5-year contract), and then $41.358 million of $65.3 million over the first three years for Mitch Marner’s 6-year contract (all via capfriendly.com). The Leafs and MLSE are the richest organization in the NHL and this provides an advantage for them over nearly every other team when signing contracts.

As articulated by Adam Wylde (@AdamWylde) in the most recent episode of the Steve Dangle Podcast, “This is an organization that’s worth over several billion dollars … with Alex Pietrangelo, he’s going to look at that and go yes, I could make eight million bucks a year and get some bonuses and stuff from St. Louis, or, in the next three years in Toronto I can make 50 million dollars.” The Toronto Maple Leafs and MLSE’s bank account has the ability to do that, looking at the St. Louis Blues, they do not.

The only current player on the Blues active roster with any signing bonuses is Ryan O’Reilly who has $45.5 million of his $53.5 million contract paid in signing bonuses. But that contract and those signing bonuses weren’t even signed by the Blues organization. O’Reilly signed that deal as an extension with the Buffalo Sabres back in 2015 before being traded to the Blues in 2018.

No other player on that Blues team has any form of signing bonuses or performance bonuses (with the exception of Robert Thomas and Pietrangelo making very minor performance bonuses). That’s two players. Just for comparison, the Leafs have 12.

Not Only for Negotiations but Trading too

Not only does this strategy of frontloading deals with signing bonuses attract players to come here with money security pretty much for life, but it also makes these contracts much more tradable for the future (bearing no forms of NTC/NMC’s). For example, when teams are looking to reach the cap floor, a contract with a large cap hit, but which has already had most of the actual salary paid out is very attractive.

This is what is fueling the  Freddie Andersen rumours – the Leafs have already paid 80 of the money on the final year of his deal.

Pietrangelo or Not, This Helps the Toronto Maple Leafs

For a mid-market team like the Blues, they cannot afford to live luxury like the Leafs and give tens of millions of dollars to players in the form of signing bonuses upfront. This luxury is something that the Leafs and very few other teams have at hand. It’s also why in the view of the structure of contracts, the Toronto Maple Leafs will always hold an advantage over other teams.

Not even to mention that a number of NHL ownership clubs are already attempting to cut salaries in order to cut costs in times when the league revenue stream is down. There won’t be many teams this offseason offering signing bonuses to players quite like what we’ve seen over the past couple of years. And in the minority of teams that will, the Leafs will be one of them.

Whether it’s going to be in the form of Alex Pietrangelo, Chris Tanev, Jacob Markström, or any other big names that the Leafs target this offseason, or in any future contract negotiations for that matter, this advantage will come to serve the Leafs well for years to come. Sometimes it pays to be rich.