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Three Leafs that got away

St Louis Blues v Colorado Avalanche Photo by Doug Pensinger/Getty Images

As we all know, the Leafs haven’t been the most clever front office over the last decade or so. Consequently, there have been many players that the team has traded or not re-signed who have gone on to great things with other teams. Today, we’ll take a look at three players who’ve slipped away from the Leafs in recent years (2008/2009 season onwards) and made the team pay for it. We’ll also look at whether the move was a foreseeable mistake at the time.

Alex Steen

How he left: Via trade with St. Louis in November 2008.
TOR received Lee Stempniak (W), STL received Alex Steen (C/W) and Carlo Colaiacovo (D)

At the time: Steen was struggling through a season where he had just four points in 20 games with the Leafs, while being relegated to 3rd and 4th line duty by head coach Ron Wilson. Despite having shown promise in prior years, the fanbase and management had started to sour on the 24 year old, opening the door to him being traded.

Colaiacovo was an injury prone defenseman who had been criticized by Wilson for his lack of fitness, though he was a young and cheap depth defenseman at the time.

Stempniak was considered a player who could play in the top six of the Leafs, having tallied 52 points in his sophomore year in 2006/2007. While his numbers declined in 2007/2008, he was still viewed as a young, talented player with notable offensive upside.

How it turned out: Steen exploded in 2009/2010 at the age of 25, and blossomed into one of the best forwards in the NHL, playing on a St. Louis team that became a perennial regular season power. Not only did Steen’s counting numbers explode (with his points per game in St. Louis being 50% higher than they were in Toronto), but he became one of the most dominant shot results players in the league, and a poster-child for the early days of hockey analytics.

Since 2009/2010, Steen ranks 55th league wide in 5v5 Points/60 (among players with more than 2000 minutes in that time frame), putting him among the better scorers in the league. At the same time, he made a strong possession team even better when he hopped over the boards, driving both shots and goals at a high level. He’s one of the most underrated players of the last five or six years, and Toronto had him.

Stempniak had 1.5 decent seasons in Toronto, averaging about 0.5 points per game, but was traded as an expiring contract to Phoenix in 2009/2010 for Matt Jones (who?) and 2010 4th and 7th round picks (it’s the Leafs, so I don’t need to tell you that these did not produce NHLers). In the end, this deal was a huge win for the Blues, and a huge loss for the Leafs. The Blues got one of the league’s best forwards for five years. The Leafs got 18 months of a pretty good winger.

Was it stupid?: To an extent, yes. Steen was quite clearly a talented player who was being buried by a tough-love coach. And while Stempniak had put up an excellent sophomore season, a deeper look shows that his goal numbers were bolstered by an irregular 16% shooting percentage that year. Even ignoring the unsustainability of Stempniak’s season, Steen had put up roughly similar scoring rates at the time of the trade, and was a year younger. The Leafs traded Steen at his lowest value, in the midst of a tough slump in the pressure cooker Toronto market, for a player who represented a very marginal upgrade. They also threw in Colaiacovo, just for good measure.

That said, no one thought Steen would become as good as he did, and that includes St. Louis. Nonetheless, it was a dumb move, both at the time, and in hindsight (something that has been quite typical of the Leafs).

Clarke MacArthur

How he left: Left via free agency. Signed with Ottawa for 2 years, $3.25M AAV before the 2013/2014 season.

At the time: After signing with the Leafs in the summer of 2009, MacArthur spent the next three seasons being a solid, cost-effective scoring winger who helped drive play for the Leafs. Most notably as part of the M-G-K line (MacArthur - Grabovski - Kulemin), he was a bright spot on a team that didn’t have many. He was also an under-utilized player on the one Leafs playoff team of the last decade, being played up and down the lineup despite excellent scoring numbers (2.02 5v5 Points/60, which is a first line scoring rate) and ridiculous shot results (7.3% 5v5 CorsiRel). This culminated with him being scratched in Game 1 of the Leafs first round series with Boston. After a lopsided loss, Carlyle played him the rest of the series, where MacArthur was one of the best Leafs. But the damage was done. A free agent in the offseason, MacArthur never considered returning to the Leafs with Carlyle behind the bench, and the Leafs lost him to rivals Ottawa, who signed him to a very team friendly deal.

How it turned out: MacArthur had an excellent start to his Senators career, posting 55 points in 79 games in 2013/2014, vastly outperforming his contract. His second year with the team was less successful, though still very good from a points perspective. In increased minutes, he also continued to be a respectable shot driver. Ottawa rewarded him with a 5 year contract worth $4.65M annually. Unfortunately for him and the team, he hasn’t gotten a real chance to live up to it. Concussions have put a damper on each of his last two seasons, and prevented him from getting any real game time last year. Aside from the obvious health and well-being concerns, it makes the contract he was given (before any real concussion history) less of a slam dunk than it appeared at the time. Nonetheless, Ottawa got an excellent winger for bargain-bin prices in his first two years with the club, and the Leafs ended up with cap space for their ill-fated 2013 offseason.

Was it stupid?: Oh god, yes. MacArthur was one of the Leafs best players, and just as critically, he was someone who was vastly undervalued by the market. By choosing to continue to employ Carlyle, the Leafs drove that incredible value away. In fact, the guy who took MacArthur’s spot in the lineup was none other than David Clarkson... you don’t need me to tell you which one would have been better to sign in the summer of 2013.

John-Michael Liles

How he left: Via trade to Carolina in January 2014.
CAR received John-Michael Liles (D) and Dennis Robertson (D), TOR received Tim Gleason (D)

At the time: Liles had a weird tenure in Toronto. After being acquired by Toronto in the summer of 2011, he was sidelined by concussion issues later that year. The Leafs nonetheless saw fit to sign him to a 4 year extension worth $3.875M per year in January 2012, without seeing how he recovered from the injury. Predictably, Liles struggled upon returning to the lineup, and his contract quickly became a bit of an albatross. It was expected that the Leafs would use a compliance buyout on his deal in the aftermath of the 2012 lockout. They decided to buy out Mikhail Grabovski and Mike Komisarek instead. Enough digital ink has been spilled regarding that decision.

Liles continued to toil on the periphery of the Leafs defence. After being waived and recalled mutiple times in the early part of the 2013/2014 season, Liles was traded to Carolina (along with prospect Dennis Robertson) for Tim Gleason on the day of the 2014 Winter Classic.

How it turned out: Predictably terrible. As soon as he left Toronto, Liles flourished under coach Not Randy Carlyle. He immediately became a positive shot-results player who was helping drive play for a surprisingly decent Carolina team that was undone by poor goaltending. He wasn’t a world-beater, and he probably still wasn’t worth his contract, but the Leafs front office treated him as though he was a borderline NHLer. He clearly still had a lot to give, and like many players, succeeded away from Carlyle.

Giving up Liles for nothing wouldn’t have been great, but what the Leafs ended up getting back was much worse. Tim Gleason was more expensive and worse than Liles with his contract having the same term. In fact, he was so bad, that the Leafs chose to buy his contract out in the summer of 2014, which will remain on the Leafs books until after 2018/2019.

So to recap, the Leafs traded the better player with the better contract, then bought out the player they received six months after the trade for a cap penalty that will extend for another two years. All this when they could have used a compliance buyout instead. And the player they traded ended up being pretty good away from Randypuck, and could have been used by the Leafs considering their perennially weak blueline. This was not a banner moment for the Nonis era.

Was it stupid?: Read the above paragraph