While the Stanley Cup Finals are finally nearing their conclusion, talk is already building around the NHL offseason and the chase for a big-name free agent.

After a year of speculation, it is now confirmed that St. Louis Blues captain Alex Pietrangelo will hit the open market on Oct. 9. and the Toronto Maple Leafs are salivating at the prospect of another established NHL star possibly coming home.

Pretty much any time a player from the GTA becomes available, Leafs fans are convinced that they will sign with the Buds. And in 2018, their beliefs were reinforced when John Tavares actually did.

But Pietrangelo is a whole other kettle of fish.

As the Leafs well know, players like the King City, ON-native do not grow on trees. They have been trying to find someone like him to come rescue their swiss cheese defence for years. And there is no time like the present to grab the player who could finally solve their problems.

And regular reports from NHL insiders claiming that Pietrangelo and the Maple Leafs have a mutual interest have done little to temper expectations.

But given the Maple Leafs massive contracts and a flat cap, trying to bring the top free agent on the market to the Big Smoke is going to be a massive challenge.

The Pietrangelo Fit

For years, the Maple Leafs have been looking for one specific player: a physical, right-shot defenceman.

By almost any measure, Pietrangelo is exactly what the boys in blue are looking for.

At 6’3, 210 lbs and shooting right, the Blues captain checks all the physical boxes.

He is also a big-time minute eater, finishing top ten in the league in total time on ice and 14th in minutes-per-game with 24:11, one second less than the Leafs top D-man Morgan Rielly.

While adding size to the back end, Pietrangelo also can provide further support to the Leafs lethal offence. He has averaged 47 points a season when he has played 70+ games.

However, despite his imposing size, the Blues captain is not a bone-crushing defender. He only handed out 1.66 hits per 60 last season, which would rank him 26th compared to the Leafs, less than every regular Toronto defenceman.

That does not change the fact that Pietrangelo is still a number one defenceman capable of matching up with and shutting down opposing stars.

Off the ice, the 30-year-old would be also provide some much-needed experience and maturity, things the Leafs are desperately lacking. 

There is no question that the Maple Leafs can succeed in the regular season, but playoff success is still elusive as this generation has yet to win a series.

Pietrangelo has not only won a cup, but he captained the team and played in more playoff games during that cup run than any individual on the current Leafs roster has in a Toronto uniform.   

The Leafs Cap Situation

The number one challenge in bringing Pietrangelo to Toronto is the salary cap.

Throughout his tenure as GM, Kyle Dubas has bet on the cap going up. Now, by no fault of his own, that strategy has dramatically backfired due to the COVID-19 pandemic and the flat cap that has resulted.

As of now, the Maple Leafs only have $6.1 million to spend under the salary cap.

While that may seem like a decent number, it is complicated by the fact that they only have 18 players under contract, not even enough to field a team on any given night.

Currently, the Leafs have nine forwards, seven defenceman, and two goalies under contract. However, that count includes rookie Nick Robertson, who likely earned himself a spot on the regular season roster after a solid playoff performance, as well as Swedish defencemen Rasmus Sandin, Timothy Liljegren, and Calle Rosen, all of whom had stints with the big club but spent most of 2019-20 with the AHL’s Toronto Marlies.

The team has nine players headed to free agency, five restricted.

So the Leafs are going to need to find some bodies, especially up front, to fill out the roster before worrying about Pietrangelo.

After terrible seasons, defencemen Tyson Barrie and Cody Ceci are almost certainly departing. Just last week Kyle Clifford, the Leafs top physical forward, announced he would test the market too.

The players that are most likely to consider returning are Jason Spezza, Ilya Mikheyev, Travis Dermott and Frederik Gauthier.

The last three are RFAs, but Spezza will be unrestricted. The 37-year-old took a discount to play in Toronto last off-season and, despite a rocky start under former coach Mike Babcock, was a key presence, providing some much-needed maturity. Spezza can probably be brought back for a similarly low contract.

The three RFAs are a little more complicated.

The most challenging will be Dermott. At 23, he will likely be looking for a considerable raise. Based on recent contracts signed by defenceman of the same age, he could be looking for something in the vicinity of $4 million considering he spent considerable time on Toronto’s top pair this season due to Rielly and Jake Muzzin’s injuries.

Perhaps he could take less or take a lower bridge deal, but so far Dubas has a terrible track record of getting team-friendly deals from young players.

The absolute best-case scenario cap-wise for the Leafs would be getting Dermott just under $3 million, likely on a bridge deal. But recent history would suggest that this is unlikely so a contract between $3 and $4 million is probable.

Mikheyev is a little tricky as a KHL import and the fact that he missed a huge chunk of the season with a fluke injury.

Prior to getting hurt, Mikheyev had impressed, picking up 23 points in 39 games. And with the Kasperi Kapanen trade, the Leafs currently only have one right-winger under contract which makes bringing back Mikheyev event more crucial.

The Russian is probably due for a raise, but given the fact that he has not played a full season as a Leaf, it will probably be a small raise, maybe narrowly breaking the $1 million mark.

As for Gauthier, he is the most likely RFA to be let go, although he is also probably the cheapest to re-sign. The 27-year-old was a regular in the Leafs line-up for the second year in a row as the fourth-line centre.

Even he is re-signed, it is unlikely that he would garner much more than his entry-level cap hit of $836 thousand.

Bringing back those four free agents would bring the Leafs roster up to 22 men, 12 forwards, eight defencemen and two goalies. They would need one more for a full roster, a spot perfect for Pietrangelo.

However, re-signing Spezza, Dermott, Mikheyev and possibly Gauthier would leave the Leafs with around $1 million left under the cap.

Cap clearing options

$1 million will not be nearly enough to sign Pietrangelo. In fact, the $6 million Toronto currently has probably is not enough considering the cap hit on his previous contract was $6.5 million and he is looking for a raise.

Rumour is that Pietrangelo has been looking for a contract in the vicinity of $9 million a year, way outside the Leafs range. Supposedly he turned down an offer from the Blues of $7.7 million per year which gives a ballpark of how big a contract the D-man is looking for.

Even if the King City-native did take a hometown discount to come play in Toronto, it is hard to imagine him settling for less than the Blues offered.

So how can the Leafs find the space to sign him?

Trade a big piece

The easiest way to make room for a big contract would be to get rid of a big contract.

The Leafs are currently paying just under 50 percent of the cap to four players: Auston Matthews (11.6), John Tavares (11), Mitch Marner (10.8) and William Nylander (6.9).

Getting rid of any one of them could be enough to sign Pietrangelo.

But how likely is it one of them gets dealt?

First and foremost, Matthews and Tavares are not, under any circumstances, going anywhere.

Marner is untradeable. He has a horrific contract and is coming off a terrible season. Of course, the entire point of trading him would be to clear salary so the Leafs could give him away for nothing and that would be considered a win.

But Marner, when on his game, is an elite winger and it would be dramatic to trade him after one bad year.

That leaves Nylander.

The problem with trading him is his $6.9 million might not be enough on its own. Someone else would probably have to go too.

But Nylander is currently looking like a bit of a bargain. He scored 31 goals in 68 games last season, second on the team. Considering the monster contracts the Leafs are dealing with, having a 30-goal scorer for under $7 million is a good property to have.

Despite all the animosity and his terrible 2018-19 campaign, Nylander bounced back well and made himself very valuable last season. It would be a shame to see him go.

So it is pretty unlikely that the Leafs would trade any of the big four to make room for Pietrangelo, which may be for the best.

Trade some smaller pieces

The more likely, and more discussed, scenario is that the Leafs trade a few smaller pieces to clear the necessary cap space.

Andreas Johnsson and Alex Kerfoot are two names that have been floated. Both carry $3.5 million cap hits and were useless in the playoffs.

Kerfoot had a mere nine goals and 28 points in 65 games in the regular season since after coming over in the Nazem Kadri trade last summer.

Johnsson missed the final weeks of the regular season with a knee injury before returning in the playoffs. He only had eight goals and 21 points before his injury.

While both provide depth, neither were key components of Toronto’s offence. Johnsson was on pace for fewer points than the previous year before going down with injury. And Robertson makes him expendable.

Trading Johnsson and Kerfoot would clear $7 million from the cap.

Another option would be to let the RFAs and/or Spezza walk which would help clear space.

The other big name being hotly discussed for a trade is Frederik Andersen.

Many pundits have said Andersen has played his last game as a Maple Leaf. It has also been reported that Dubas has received calls inquiring about the Leafs netminder, although he has said he is not actively shopping Andersen, just listening to calls.

Andersen carries a $5 million cap hit which would go a long way to clearing space for Pietrangelo, except he would then have to be replaced which would limit how much cap space is gained.

And replacing Andersen will be a tall task.

The Dane is an upper-tier goaltender and it will be nearly impossible to replace his quality for less money.

No, Matt Murray is not a viable alternative.

The argument for trading Andersen is that he plays badly in big games. It is true that he has a terrible record in the playoffs since coming to Toronto. But in his defence, the entire team has played terribly in deciding games.

This season, he was given no offensive support in the decisive game five against Columbus. Even in game four, Toronto failed to score at even strength when trying to stay alive. The year before the Leafs only mustered one goal in game seven against Boston.

A goalie cannot do it all themself.

Besides, Andersen has been the unsung hero of the team throughout his tenure. Without him and his outstanding play, it is unlikely that the Leafs would even make the playoffs.

Since being traded to Toronto in 2016, Andersen has faced more shots and made more saves than any goalie in the NHL. He has ranked in the top four in both those categories every season as the Leafs netminder.

He was also often saddled with a garbage back up, forcing the Dane to play too many games in the regular season.

These factors combined led to him being exhausted come the playoffs, which contributed to his poor play.

Those are defensive issues, not goalie issues. And not only would another goalie not do better under these circumstances, a cheaper goalie would probably do worse.

In short, the Leafs are not going to find a goaltender as good as Andersen for less money.

What is the point of fixing your defence if you are not going to have a good goalie?

Of all the ideas being floated about how the Leafs could find a way to sign Pietrangelo, trading Andersen is a knee-jerk reaction that makes little sense.

In any case, if the Leafs are to clear the way to sign Pietrangelo, some combination of the players named above would likely be on the move.

What if he does sign?

Finding a way to sign Pietrangelo might help solve one big problem, but it would create a lot of others.

Most likely, signing the D-man would mean shipping out multiple players. Considering how few bodies the Leafs currently have under contract, they would face a major challenge to get their roster up to 23 men.

And factoring in that Pietrangelo would likely take up all the rest of the cap space, the Leafs would have to scrape the bottom of the barrel for cheap players to fill out the roster.

Toronto’s offensive depth was supposed to be one of their biggest assets. But clearing cap space for another big contract would almost certainly mean abandoning that.

What if Andersen is the one to go? Who is going to play in net? Especially if there is little cap space left.

There is no easy solution here and is begging for disaster. Jack Campbell was a great acquisition as a back up, but can he be the starter? Is there a starter they can sign for less than Andersen’s rate? Probably not a good one.

It would be great to fix the defence, but goaltending could be the cost which would negate the forward progress.

Goaltending is not the only position that could be a problem depending on who gets dealt.

Kerfoot, Spezza, and Gauthier all have taken turns at centre. If some combination of them goes, the Leafs will need to find themselves another capable bottom-six centreman.

Pietrangelo would bring the Leafs to four regular-roster defenceman. Five if Dermott is not a casualty of the pursuit. That could work, but if Dermott goes the Leafs will have a pretty exposed bottom pair.

That would throw Sandin and Liljegren into the spotlight. They would have to be ready to go.

Sandin showed promise in his time with the big club this season, but Liljegren has been marinating in the minors for years and still has struggled to establish himself with the big club so he is not exactly reliable.

Signing Pietrangelo could also make that first round pick acquired from Pittsburgh even more critical because it is a chance to pick up a key player for cheap by drafting well.

Put simply, bringing in Pietrangelo would cause crazy cap and lineup headaches.

Nothing is impossible but given the amount of jimmying necessary to make him fit in Toronto, it seems highly unlikely that Pietrangelo will suit up in blue and white any time soon.

And that might be for the best.

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