How the Leafs have approached July 1 during the Shanaplan era so far

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When the market opens tomorrow at noon Eastern Standard Time, the Toronto Maple Leafs will have the available salary cap space to be major players.

The Maple Leafs don’t have many key restricted free agents to sign (none of Peter Holland, Connor Carrick, Frank Corrado, or Martin Marincin will command a big ticket). They have a couple of big contracts could be placed on LTIR once the season begins. Because of this, Toronto could responsibly spend as much as about $12 million on the free agent market. 

It seems unlikely that the Leafs will have any inclination to use all of that space, though, especially now that we know for sure that Steven Stamkos is staying put. As part of projecting what the Maple Leafs might do, though, perhaps it’s worthwhile to look back at what the club has done on July 1 in the years since Brendan Shanahan became president. 

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In 2014 Brendan Shanahan was relatively new on the scene. He still hadn’t handpicked his current management team or even completed his evaluation of those who were then on the Maple Leafs staff. Randy Carlyle was still the head coach. Dave Nonis was general manager and Dave Poulin and Claude Loiselle were still serving the club as assistant general managers. 

It would take a while for Shanahan, in his deliberate style, to put his fingerprints on the Maple Leafs organization. Assistant general manager Kyle Dubas wasn’t hired until late July of 2014, and assistant to the general manager Brandon Pridham, who retained that title even during the long gap between Nonis’ firing and the hiring of Lou Lamoriello, wasn’t hired until late August. Dubas didn’t build his ‘veritable army of nerds’ until later that summer also.

Shanahan may have had his paws on the steering wheel by the time the market opened on July 1st, 2014, but the road map was being interpreted by voices wildly different than those who make up the Maple Leafs front office today. Perhaps unsurprisingly, those voices seem to have advocated a course of action with a greater apparent relation to some of the decision making that predated Shanahan, than with how the Maple Leafs currently conduct themselves. 

Immediately before July 1, the Maple Leafs bought out defenseman Tim Gleason freeing up some additional cap space. It was an appropriate end to Gleason’s tenure as a Maple Leaf, which just never should’ve happened. 

On July 1 itself, the club seemed to pursue a ‘get the band back together’ sort of approach, which isn’t an uncommon approach for an embattled front office – as Nonis, Poulin and Loiselle surely knew they were after the Shanahan hire – to take. Effectively, it seems, they opted to double down on what “worked” before. 

First, the club completed a July 1 trade sending Jerry D’Amigo to the Columbus Blue Jackets for Matt Frattin, still considered by some to be an NHL piece back then, and a conditional seventh-round pick (the condition of which was never met). Frattin and his loud skill set – that hard wrist shot, the speed, the board-rattling hits – was a mainstay of the Carlyle-era Maple Leafs, but he only played nine more games for the club after his re-acquisition.

On the unrestricted free agent market, the Maple Leafs chased two bigger name players: Dave Bolland and Stephane Robidas. Bolland ultimately took more money to go to Florida, but the Maple Leafs signed Robidas – who is now a fixture on long-term injured reserve.

Let’s rehash the Bolland thing a little bit further before moving on here, because his contract is a big part of this story. Currently, Bolland isn’t healthy enough to be bought out and his contract – a five-year deal worth $27.5 million – is a millstone that is almost without comparison in the league at the moment. David Clarkson’s contract is bad and all, but at least he can take a regular shift at the NHL level. If Bolland ever hits the ice again for the Florida Panthers, it will be a surprise.

How close were the Maple Leafs to making the catastrophic error of landing Bolland? It depends on who you ask. Bolland himself on July 1, 2014, suggested that they weren’t really in the same ballpark.

“There were only about two or three teams that were down in the mix,” Bolland told Rogers Sportsnet, via Sean Fitz-Gerald then of Postmedia News. “It came down to two of them, and that was Toronto and Florida.

“Florida was there,” Bolland added later in the interview. “I think the agreement between us and Toronto just wasn’t there. I don’t think we were getting to the right kind of money.”

If Toronto wasn’t willing to match Florida, it seems they were willing to get close. TSN’s Darren Dreger reported on June 30 that the Maple Leafs weren’t ready to go past five years and $25 million. The obvious implication there is that the Leafs were willing to meet that figure. And it seems possible that the Leafs went a bit higher than that at the last minute, based on Dreger’s suggestion on July 1 that Leafs brass was “meeting internally” to design one final pitch to the third-line centre.

As for Robidas, the Maple Leafs landed him on a three-year contract worth $9 million. Robidas was 37 at the time and was coming off of a season in which he’d sustained a brutal leg fracture during a freak collision along the end boards. He rushed back, was actually dealt for a decent return to the Anaheim Ducks at the trade deadline, and managed to come back for the stretch run, appearing in three playoff games for Anaheim. 

Concerning pain tolerance and his commitment to the sport, what Robidas accomplished was enormously impressive. And until that injury he’d been among the league’s most reliable defensive defenseman for several years, even a forerunner of the now en vogue ‘transitional defensive defenseman’. 

It should also be noted – because second guessing decisions two years hence is unfair anyway, but especially if we don’t add proper context – that Robidas fared pretty well down the stretch with the Ducks after his injury.

With all of that said, in terms of how Robidas projected over the life of the deal the Maple Leafs signed him to, well, it was apparent even at the time that the Maple Leafs were making a dicey gamble – even if it was one that a variety of other teams would’ve made willingly.

Needless to say, Robidas isn’t going to play again in his hockey career, and only ever suited up in 52 games in his Maple Leafs career. 

Finally, the Maple Leafs made one more major deal. It was widely panned at the time but is looking better and better as time passes. They signed Leo Komarov to a four-year, $11.8 million contract that carries an annual average value just shy of $3 million. 

At the time the deal seemed ridiculous, even if it was the cost of doing business to sign a player who had a good amount of leverage because of his appeal to KHL teams. Komarov, after all, had only managed nine points in 42 NHL games to that point in his career. 

Since signing that deal, Komarov has developed into a genuine top-six forward with enormous defensive value. He’s now improving the defensive play of whatever line he flanks and is providing an enoromous level of surplus value. Maybe we needn’t have been so surprised. 

Though the Komarov contract salvages the day somewhat, in Shanahan’s first free agent frenzy as Maple Leafs president the club signed an aging player coming off of a trying injury to an enormously risky contract, were narrowly outbid for one of the worst contracts in the NHL, traded a farmhand for a farmhand, and found some unlikely value by committing long-term to a player that, at the time, was largely unproven at the NHL level. 

It wasn’t a great day for the Maple Leafs by any measure, but fortune smiled. It could’ve been a lot worse.

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Let’s fast forward a year to another dramatic free agent frenzy for the franchise. 

In 2015 the Maple Leafs front office had a wildly differently look than the group that was advising Shanahan a year earlier. Pridham and Dubas had nearly a year under their belts, Nonis and Carlyle were gone, and the team was without a full-time general manager. The club had just completed the coup of landing Mike Babcock as head coach.

The current Maple Leafs front office was mostly in place, with one notable exception: current general manager Lou Lamoriello. Lamoriello wouldn’t join the club until later in the summer of 2015.

Entering July 1, the rumblings were all centred around the trade market. Tyler Bozak was supposed to be in play and questions about whether or not the club would deal Phil Kessel dominated Twitter and the airwaves. There was a widespread suggestion that with Maple Leafs head coach Mike Babcock about to enter his first season with the club, perhaps the incoming coach might prefer to see what he might have in Kessel rather than see him prematurely dealt. We all know how that turned out. 

Toronto was also being linked to higher-profile players like Michael Frolik and Matt Beleskey – both of whom ultimately signed elsewhere for reasonably big tickets with lots of term. 

In free agency, at least, the Maple Leafs took a conservative approach. The day began with the Maple Leafs signing Matt Hunwick to a two-year contract worth $2.4 million. Hunwick quickly became a Babcock favourite in his first season in Toronto, handling tough assignments (poorly) and soaking up a tonne of minutes. 

Hunwick will be with the team again next season, and though he’s probably best suited to playing a depth role, from today’s vantage point, it seems likely that he’ll remain entrenched in Toronto’s top four – at least through the 2017 NHL trade deadline.

A bit later in the day, the Maple Leafs signed P.A. Parenteau to a one-year deal worth $1.5 million. It’ll be curious to see what the team decides to do with Parenteau when the market opens. The playmaking winger exceeded all reasonable expectations with the Maple Leafs and is likely to look for term on the open market. On a one year deal, Parenteau was a great fit, even if the Maple Leafs weren’t able to liquidate him at the deadline for additional futures. 

Going forward is he worth committing term to? On a modest contract he might be, but if the club was eager to do that, you’d think they would’ve extended him by now…

Having completed two low-cost, conservative signings; the Maple Leafs went bold. They made the deal of the day trading Phil Kessel to the Pittsburgh Penguins along with a conditional second-round pick, Tim Erixon and Tyler Biggs in a retained salary transaction in exchange for a conditional first-round pick, Kasperi Kapanen, Scott Harrington and Nick Spaling.

The Kessel trade isn’t all that controversial a year on. The Penguins went on to win the 2016 Stanley Cup championship and Kessel is bringing the best trophy in sports to Toronto to host his ‘day with the Cup’. Superficially speaking the Penguins, and Kessel himself got the better end of this trade.

That said, the Kessel deal did fit a long-term vision for the club. For example, the Maple Leafs opened up a tonne of cap space with the Kessel trade, which gave them the flexibility to take back undesirable contracts in a variety of deals. This flexibility, in part, helped them get rid of Dion Phaneuf’s bloated contract, and it gave them the space to take on Brooks Laich’s contract – with the benefit that the Washington Capitals sweetened that deal considerably.

In terms of moving on, continuing to accumulate assets and using cap space and the organization’s deep pockets to achieve those ends, trading Kessel was at least logically consistent with the club’s wider goals. And we should note that losing Kessel – a genuinely elite offensive piece helped the Leafs bottom out. If Kessel scores 30 the club probably doesn’t place 30th, but finishing in dead last resulted in Toronto owning the best draft lottery odds and eventually the first-overall pick. I don’t think it’s unfair to draw a direct line from the Kessel trade to Auston Matthews’ selection in Buffalo last week…

In terms of tying off loose ends from this deal, Spaling became another second-round pick in a deadline day deal with the San Jose Sharks and Pittsburgh’s first-round pick was used as currency to buy Frederik Andersen, a goaltender that the Maple Leafs see as their starter for the foreseeable future. Meanwhile, Scott Harrington was flipped to the Columbus Blue Jackets for Kerby Rychel, and Kasperi Kapanen had a solidly impressive, but not world beating, AHL season as a 19-year-old. He remains a very good prospect.

As the hockey world was still processing the Kessel trade, the Maple Leafs continued to make modest, conservative bets in free agency. 

The club re-signed Richard Panik to a one-year contract. Panik was fine depth and the club dealt him to Chicago for Jeremy Morin, who they then traded to San Jose as part of the James Reimer deal, which also netted the club a conditional fourth-round draft pick in 2018. That pick became a third-round pick thanks to the San Jose Sharks advancing to the Stanley Cup Final in 2016.

Then the club signed Mark Arcobello, AHL superstar, to a one-year contract. Arcobello couldn’t stick in the show with the Maple Leafs last season, but was a better than a point per game contributor for the Marlies and helped make them the can-opener offensive team that ran roughshod over the rest of the American League in the regular season. Already this offseason Arcobello has signed with a Swiss NLA club and won’t be back in the organization next year.

Finally, the club signed Daniel Winnik to a two-year, $4.5 million contract. Winnik brought his usual, dependable north-south game to the Maple Leafs and played well enough that the Capitals traded for him at the deadline. In exchange for taking on Brooks Laich’s oversized contract and sending Winnik and a fifth-round draft selection to Washington, the Maple Leafs were able to add a legitimate right-handed defense prospect in Connor Carrick and a second-round pick. 

So let’s summarize this. The Maple Leafs went into the 2015 free agent frenzy day linked as a suitor to a variety of non-star players who signed for big money and term. Instead, the Leafs eschewed that approach and opted to make a handful of smaller signings and one huge trade. 

The club signed Panik, Arcobello and Parenteau to one-year contracts – none of which exceeded $1.5 million in total value. Arcobello was a key American League contributor; Parenteau was a key NHL-level contributor and Panik was turned into a AAAA scoring stud who was thrown as a signed contract into the James Reimer trade, which ultimately netted the Leafs a third-round pick a couple of years down the road. That’s all well and good and inexpensive.

The club also signed two players to two-year deals – none of which exceeded $4.5 million in total value. Winnik has since been traded for a second-round pick and a genuine prospect, although we can’t ignore the role that Laich’s cap hit played in sweetening that deal from a Maple Leafs perspective. Getting rid of that cap commitment was as attractive to the Capitals, probably even more so, than acquiring a solid bottom-six forward for their playoff run.

And that spare cap space was available to the Maple Leafs, in part, because of the Kessel deal. Though the Penguins got the better end of the Kessel deal, in the year since the trade, the Maple Leafs achieved two crucial things as a direct result: they used that cap space to their advantage in accumulating assets and weakened their team to the point of a 30th place finish and, with the grace of the lottery balls, the first-overall pick. 

Toronto also used one of the two premium future assets in that trade (the conditional first) to land a promising and relatively young goaltender that looks like a decent bet to be an average starter. They dealt the journeyman forward they acquired as part of the Kessel trade to the Sharks in exchange for a second-round pick. Toronto missed on Harrington, but Kapanen is still a promising young player, even if he still might need a year of seasoning before he’s ready for an everyday job at the NHL level.

I don’t know if we should go as far as describing the Kessel deal as a good move for the Maple Leafs, but a year on, it’s easy to see why it was a necessary part of the Shanaplan.

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So now, as we prepare for a much-needed long weekend, we wait. 

Tomorrow the 2016 free agent frenzy will be upon us. It’ll be Lou Lamoriello’s first July 1 as Leafs general manager, and it’ll be fascinating to see what impact, if any, he has on the club’s overall direction. 

In contrast with what went down on July 1 in 2014 and 2015, I think it’s fair to expect the Maple Leafs to be relatively quiet – especially now that Stamkos is off the board. 

As it stands the Maple Leafs are a fringe playoff team at best, but a very young and potentially exciting fringe playoff team. With that in mind, maintaining long-term salary cap flexibility while adding depth, ideally by making smart short-term bets, should probably be the order of the day. If the club can continue to move out older players on more expensive contracts – Joffrey Lupul seems close to immovable, but surely Tyler Bozak retains some value – then all the better. 

As we saw in 2014, big mistakes can – and often are – made rapidly on July 1. And as we saw in 2015, shrewd forward-looking deals, even if they don’t work out exactly how a management team draws them up, can be used to strengthen a club’s overall position.