Down Goes Brown: The five worst free agent signings of the past 20 years

David Clarkson, Paul Kariya and Teemu Selanne, Bobby Holik. (Getty Images)

Free agency opens on Friday, as teams will be officially allowed to sign players on the open market, and fans around the league should be excited.

No, wait, excited isn’t the right word. What’s the one I’m looking for? Terrified. That’s the one. You should all be terrified.

That’s because, despite the occasional success story, NHL teams tend to be terrible at signing free agents. They can’t help themselves. And it rarely takes long for the initial excitement of a big signing to give way to the realization that a team has just handed out too much money for way too many years.

As we count down to Friday’s deadline, let’s take some time to look back at some cautionary examples of how quickly a big deal can go bad. Here are my picks for the five worst unrestricted free agency signings of the past two decades.

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Auston Matthews reacts to putting on the (new) Leafs jersey for first time

Matt Larkin
Auston Matthews. (Getty Images)

BUFFALO –– The moment was surreal. Especially considering where the Toronto Maple Leafs franchise was even two years ago. Lou Lamoriello and Mike Babcock, standing on the stage, handing a sweater to the first overall pick in the 2016 draft, representing the Blue and White? Did Leaf Nation dream this? Nope.

Toronto selected what it believes will be a franchise-defining player in center Auston Matthews. It was only fitting that, when Matthews donned his Leafs jersey, he became the first player to do so. The old getup, associated with too many years of failure, wouldn’t do. The “new” look includes the veined logo worn from 1938 to 1963, a period during which the Leafs won eight Stanley Cups. The rest of the design is understated, simple and classy: two horizontal stripes on each arm and some thicker piping along the bottom.

“It looks good,” Matthews said. “I like it. It felt unbelievable putting on the jersey. Such a storied franchise, so it was a big honor.”

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Auston Matthews: From the Arizona desert to the Center of the Hockey Universe

Ryan Kennedy
Auston Matthews. (Minas Panagiotakis/Getty Images)

Surely, the Matthews residence in Scottsdale, Arizona is a lovely abode. But when Auston Matthews was growing up, he tended not to stay within its walls for very long, even through the Xbox era. That’s because there were always sports to play outdoors. The neighborhood was full of kids up for games of football, soccer and basketball, while organized hockey and baseball went year-round thanks to summer hockey all-star tournaments and Arizona’s perfect ballpark climate.

Auston’s father, Brian, must shoulder some of the blame for this as well, however. A college pitcher who went on to play semi-pro, he loved to challenge his son in the batter’s box. And the right-handed Brian had more than just fastballs in his arsenal against the left-batting Auston. Brian hurled sinkers and filthy stuff fathers don’t typically give sons. “I was throwing everything at him, mixing it up,” Brian said. “He never knew what was coming. But his hand-eye co-ordination was uncanny.”

Auston was a catcher and a hard-hitting one at that. Coaches told him there was more money to be made on the diamond than the ice rink, but the Arizona Kid wasn’t having it. When time constraints forced him to choose between sports at 13, baseball lost out handily. “Auston was a better baseball player than he was a hockey player, but the game wasn’t fast enough for him,” said his mom, Ema. “He needed motion.”

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THN Versus: Was now the right time for the Maple Leafs to acquire Frederik Andersen?

The Hockey News
Mike Babcock. (Getty Images)

No. What ever happened to that Maple Leafs rebuild?



THN_KenCampbell_TOP4By Ken Campbell

One of the first things that came out of Mike Babcock’s mouth after he was hired to coach the Toronto Maple Leafs last summer was, “If you think there’s no pain coming, there’s pain coming. The path we’re taking has to be different. There’s no chance for a quick fixer here.”

Well, apparently that pain threshold isn’t quite as steely and strong as we all thought. That path that was supposed to be so different? Well, accelerating rebuilds is a path so well worn in Toronto that the organization still has too look up to see ground level. And no quick fixer? How’s that working out? Well, the first chance the Maple Leafs had, they went out and got a quick fixer.

Whatever happened to that rebuild that was supposed to take place in the Center of the Hockey Universe™? Well, it went out the window when the Leafs traded two draft picks in exchange for goalie Frederik Andersen, then handed him a five-year contract worth $27 million. It’s a move that makes no sense on so many levels for a team that says it’s committed to rebuilding properly.

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Updated: Maple Leafs land Andersen from Ducks, sign him to five-year, $25-million deal

Jared Clinton
Frederik Andersen (Photo by Norm Hall/NHLI via Getty Images)

Toronto Maple Leafs goaltender Jonathan Bernier entered training camp on a brand new two-year, $8.3-million contract in 2015-16. This year it appears he’ll be heading into camp with some serious competition for his starting job.

The Maple Leafs announced Monday afternoon they have acquired restricted free agent goaltender Frederik Andersen from the Anaheim Ducks for two draft picks — the first-round, 30th-overall selection in 2016 and a second-round pick in 2017.

Anaheim had long been trying to get Andersen under contract, with GM Bob Murray saying as recently as this past weekend that he was working on getting a deal done. Murray did, however, acknowledge that eventually one of Andersen or John Gibson would have to be moved. With Gibson being the presumptive goaltender of the future, though, it seemed Andersen would be the one sent packing. Monday’s deal makes that official.

The acquisition addresses a definite need for the Maple Leafs, who were hoping to rely on, but were mostly let down by, the play of Bernier this past season. Read more

Even with Auston Matthews, don’t expect overnight success for Maple Leafs

Mike Brophy
Auston Matthews (Photo by Richard T Gagnon/Getty Images)

Members of Leafs Nation are going ga ga over the fact their beloved Toronto Maple Leafs have the first pick in the 2016 NHL draft.

And why not?

The opportunity to choose Auston Matthews and give the organization its first legitimate No. 1 center since Mats Sundin is nothing to balk at.

The Arizona native, who stands 6-foot-2 and weighs 212 pounds, is a blue-chipper who finished fourth in the Swiss league with Zurich, scoring 24 goals and 46 points and was second in voting for the league’s most valuable player award. Then, just for kicks, the 18-year-old led the United States in scoring with nine points in 10 games at the World Championship.

Toronto has not had the first overall pick since 1985 when it chose Wendel Clark.

The question is, will the addition of Matthews be the Maple Leafs instant ticket into the playoffs?

The answer, in a nutshell, is no. Not on his own.

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Maple Leafs’ Cowen, Flyers’ Umberger first players to be bought out

Jared Clinton
R.J. Umberger (Andy Marlin/NHLI via Getty Images)

The NHL’s buyout window officially opened Wednesday, and Thursday afternoon saw the Toronto Maple Leafs and Philadelphia Flyers become the first teams to take advantage of the opportunity to get rid of a contract.

Jared Cowen’s contract was the first to fall, as the Maple Leafs placed the 25-year-old blueliner on unconditional waivers for the purposes of a buyout on Wednesday. He cleared waivers Thursday afternoon to make the process official.

Cowen didn’t play a single game for Toronto and it had been clear for the final few months of the 2015-16 campaign that the Maple Leafs were going to rid themselves of Cowen’s contract come mid-June. The reason for the buyout is two-fold, though. First, Cowen doesn’t fit into what the Maple Leafs are building and he wasn’t in coach Mike Babcock’s plans, nor was he part of the future of the team. The second, much more interesting, reason is that buying out Cowen’s contract provides Toronto with a cap credit of $650,000 for 2016-17.

That’s right: the Maple Leafs earned salary space by buying out the final year of the rearguard’s four-year, $12.4-million deal. They will be on the hook for $750,000 in 2017-18, however. Read more

10 players who could be buyout candidates this off-season

Bryan Bickell (Photo by Bill Smith/NHLI via Getty Images)

Nothing says the off-season quite like the threat of buyouts, and we’re inching ever-closer to the NHL’s buyout window opening and several players could see their time with their current teams come to a close.

For some of the candidates, massive contracts are at fault, while other will fall victim to underperforming or simply not fitting within a team’s structure any longer. Unfortunately, some are a combination of all three.

With the salary cap remaining relatively flat according to all reports, several teams are going to be in tough financial situations. Even a rise of $2 million in the salary cap, which is a rough estimate of the maximum amount the upper limit will rise, would still see several teams in tough cap positions. That’s not to say all players on this list will be bought out, but there’s at least a fair chance several from this list will be sent packing by way of a buyout. Read more