Building a roster of the cap era’s worst July 1 signings

So the first day of free agency has come and gone. How did your team do?

Probably not well. If history is any guide, your team either missed out on the big signings, or paid way too much to get in on them. If we’ve learned anything about July 1 in the salary cap era, it’s that jumping in with both feet on Day 1 of the open market can lead to a lot of regret. There are bargains, sure, and occasionally a team will sign a big-dollar deal that works out great. But those are exceptions. Most of the time, July 1 is the day that GMs do their very worst work.

That feels like something worth celebrating. So as we recover from yesterday’s chaos and try to digest all the money NHL GMs just threw around, let’s look back on the mistakes of the past by building a full roster out of some of the worst July 1 UFA deals of the cap era.

A couple of quick ground rules:

– We’re only looking for UFA deals that were signed on July 1. That rules out a few names you might be expecting to see here, like New York’s Brad Richards or Calgary’s James Neal (both of whose deals came a few days into free agency) and Philadelphia’s Ilya Bryzgalov (who was actually acquired in a trade and signed before he reached UFA status, but still needs to be mentioned here because that was hilarious).

– We’re judging signings based on a mix of the reaction at the time and how the deal looks with the benefit of hindsight. Because of that second part, we’re going to try really hard not to include any of this year’s signing, although (double-checks yesterday’s list) yeah no promises.

– The 2013 offseason schedule was thrown off a few days by the lockout, so for that season only “July 1” is actually July 5.

All contract information, including signing date and cap hit percentage, is from the CapFriendly signing database. Salaries are average annual value; “cap hit” is the percentage of that season’s cap.

As you might expect, there’s going to be some overlap with our worst possible cap team exercise from last season. But as bad as that roster was, this one might be even more depressing. You’ve been warned. Let’s get started.

First line

Scott Gomez, Rangers, 2007: 7 x $7.357 million, 14.63% cap hit

This deal seemed steep at the time, and got far worse over the years. It wasn’t the complete disaster you might remember it as – Gomez was actually pretty good in his first year in New York, and nearly hit the 60-point mark in the next two. And of course, the Rangers managed to somehow unload the deal onto the Canadiens before it really blew up. But once it did, man, it was awful. When you have your own website to track whether you’ve scored, that’s bad. When that site doesn’t change for over a year, that’s worse.

David Clarkson, Maple Leafs, 2013: 7 x $5.25 million, 8.16% cap hit

“I’m not worried about six or seven right now,” Leafs GM Dave Nonis infamously said when signing the deal. “I’m worried about one. And Year 1, I know we’re going to have a very good player.”

Nope. Clarkson was a miss almost immediately, in part due to an ill-advised suspension that delayed his regular season debut. To be fair, many Leafs fans loved the deal at the time, and some of the local media went nuts for it. Others immediately saw the disaster that was coming, including a young Globe and Mail beat writer who I hear went on to work at some website.

While it was never from lack of trying, Clarkson never clicked in Toronto, and didn’t even last two seasons before the team ate millions of dollars to ship him to Columbus. He hasn’t played since 2015-16 and almost certainly never will again, but his contract is still kicking around the league – partly because Nonis decided to make it virtually buyout proof.

Milan Lucic, Oilers, 2016: 7 x $6 million, 8.22% cap hit

Three years after watching the Leafs throw seven years at an aging power forward because of heart and grit and compete level, the Oilers apparently figured they could do even better. Lucic at least gave them one decent year, which is one more than the Leafs ever got from Clarkson. But unlike the Leafs, the Oilers haven’t yet figured out a way to wiggle out from under this contract, despite rumors that they’re desperately trying.

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NHL free agency through the years

With free agency season upon us, all eyes are focused on this year's crop of UFAs. Who'll get the best deal? Who'll bolt for the KHL? Which teams will improve, and which will be left on the sidelines?

We'll know soon enough. But in the meantime, let's remind ourselves of how unpredictable free agency can be by looking back at some notable signings from recent years.

Daniel and Henrik Sedin, Vancouver, 2009 - After signing a last-minute extension with the Canucks, the twins' plans to celebrate with a slice of that big cake that showed up on their doorstep that morning are ruined at 12:01 when Brian Burke awkwardly pops out of it.

Colton Orr, Toronto, 2009 - Orr becomes one of the highest paid enforcers in league history, thanks to a deal with Toronto that pays him a quarter for every time he punches Matt Carkner in the face.

Marion Gaborik, New York, 2009 - The Rangers sign the oft-injured star to a $37.5M deal. While other teams were willing to match the money, the Rangers were the only team to meet Gaborik's demands of a "no playoff-clinching shooutout" clause.

Brian Campbell & Cristobal Huet, Chicago, 2008 - The Blackhawks sign the pair to long-term contracts that most observers feel are significantly overpriced. While many fans fear the contracts will cripple the Hawks, the front office assures fans that the team will be able to stay under the salary cap thanks to careful roster management, judicious use of buyouts, or at least some other team eventually hiring Rick Dudley.

Thomas Vanek, Edmonton, 2007 - After an 84-point season, Vanek signs a $50M offer sheet with the Oilers which the Sabres are forced to match. After realizing how close he came to spending the rest of his career in Edmonton, a shaken Vanek vows to never risk attracting the Oilers' attention again by spending the next several seasons disguised as a second-liner.

Gary Roberts, Toronto, 2000 - Roberts agrees to terms with the Leafs, choosing their contract of just under $3M a season over the Senators' offer of "Oh god, sir, please don't hurt us, take whatever you want and just leave us alone".

Chris Drury and Scott Gomez, New York, 2007 - Upon learning that critics are calling the signings the worst free agent contracts that are even theoretically possible, Glen Sather mutters "we'll see about that" and circles Wade Redden's name with a yellow highlighter.

Sean Avery, Dallas, 2008 - Upon signing Avery, Stars general manager Brett Hull tells him "Hey, I know you're better known as a Ranger, but we don't mind picking up other teams' sloppy seconds. Ha ha! Um, why are you writing that down?"

Peter Forsberg, Philadelphia, 2005 - Coming out of the NHL lockout, Forsberg shuns the Avalanche to sign with the Flyers. "I really wanted to make the right decision," Forsberg tells reporters, "because I know that the experience of being an unrestricted free agent is one I'll only ever get to have once, maybe twice, per year, for the rest of my career."

Jason Blake, Toronto, 2007 - The Leafs agree to terms with Blake early in the day, although the actual contract signing is delayed several hours due to technical problems after it's discovered that John Ferguson Jr. had earlier tried to fax himself a grilled cheese sandwich.

Trade Deadline '08 - Why it's good news for the '09 Leafs

Apparently a few readers have noted that this blog tends to take a somewhat pessimistic view of the Toronto Maple Leafs. This is probably a fair observation. I do tend to be a tad negative about the Leafs, largely due to the fact that I have two eyes and a functioning brain.

But the whole "wah wah, go cry emo fan" routine can get stale after a while. So I'm pleased to announce that this week will be Optimism Week. For one solid week, it's going to be nothing but puppies and birthday cakes here at Down Goes Brown. Enjoy it while you can, we'll be back to reality next week.

Today's post: a look at the 2008 NHL Trade Deadline, and why it's shaping up to be good news for the 2009 Maple Leafs.

I know, I know. The 2008 deadline was a disaster for the Leafs. Their desperately needed rebuilding plan was torpedoed by Mats Sundin and the rest of the loser brigade, tying the hands of Cliff Fletcher and dooming Leaf fans to another half decade of soul-crushing misery.

Hm, this optimism thing is harder than I thought.

But in addition to watching a bunch of fat millionaires destroy the Leafs rebuilding plan, the 2008 deadline was also notable for a constant theme in the coverage leading up the big day. Story after story made sure to point out that recent history seemed to show that deadline blockbusters didn't work out. The big deals in 2007, such as Ryan Smyth to the Islanders, Keith Tkachuk to the Thrashers, Ladislav Nagy to the Stars and Peter Forsberg to the Predators had all amounted to a big hill of jack squat come playoff time.

So let's take a look back at the '08 deadline, with an eye towards how the big deals have impacted the playoffs so far.

- The Penguins acquire Marion Hossa from the Thrashers - Probably the biggest deal of the day. When the trade went down, most observers agreed that the Pens had given up too much. Fast forward ahead two months, and the Penguins have rolled through the first two rounds of the playoffs, knocking out the Rangers today thanks to an OT winner by Hossa. They'll be heavy favorites in conference finals.

- The Sharks acquire Brian Campbell from the Sabres - This deal moved the Sharks from solid contender to quasi-favorite. They closed the season on a tear, and were touted by many as Cup favorites. They knocked out the Flames in round one, and as of this writing are still alive against Dallas (although hanging by a thread). Speaking of Dallas...

- The Dallas Stars acquire Brad Richards from the Lightning: Richards had four assists in his first game with the Stars, and has been a steady contributor ever since. The Stars shocked the experts by knocking out the defending champion Ducks in the first round, and are on the verge of eliminating the heavily favored Sharks in the round two.

- The Capitals acquire Cristobel Huet and Sergei Federov in separate deals - Thought to be playoff longshots, the Caps loaded up at the deadline and went on a tear. The stormed through the rest of the regular season, winning the division on the final day. While they lost a seven game heartbreaker to the Flyers, the Caps put themselves back on the hockey map thanks in part to their aggressive dealing.

Other teams also made efforts to bulk up. The Flyers added Vinny Prospal, and are headed for the conference finals. The Avs picked up Adam Foote and free agent Peter Forsberg, and won a playoff round before being overcome by injuries. The already stacked Wings picked up Brad Stuart and are looking like odds-on favorites to take the title right now.

Meanwhile, some teams stood pat:

- The Ottawa Senators were struggling badly and looked like they needed to make a big move. But as per team tradition, the went deer-in-the-headlights on deadline day, only making one minor deal for Martin Lapointe who had no impact during his Sens stint. Instead, the team continued to freefall. They almost missed the playoffs, backing in on the season's final weekend, and then were embarrassed during a listless first round sweep.

- The Anaheim Ducks, who had won a Cup the previous year without making any major deadline moves, once again stood pat. They were pushed aside with relative ease in the first round.

- The Montreal Canadiens actually managed to get worse at the deadline, moving Huet to the Caps for a draft pick. The looked strong to end the season, but their lack of goaltending depth killed their promising post-season chances. They managed a round one win over the eight seed Bruins (barely), but surrendered easily to the Flyers behind Carey Price's best Andre Racicot impression.

Bottom line: For the most part, the teams that went big at the deadline have reaped big rewards. The teams that played it cautious are sitting at home with tire treads on their jerseys.

What does any of this have to do with the Leafs? Simple. When next year's deadline rolls around, we're going to hear all sorts of talk about how the 2008 playoffs were shaped by the trade market -- especially if the Stars or Penguins win the Cup. And all that hype can only be good news for the teams that will be selling at the 2009 deadline.

And make no mistake, the Leafs will be sellers next year. When it comes time to trade whichever veterans are left -- McCabe, Tucker, Kaberle, Blake, Sundin, or even (dare I say it) Vesa Toskala – there should be a very nice seller's market waiting for them. That could translate into a nice windfall if the new GM plays his cards right.

It will be a year too late, but good news delayed is still good news.

The Price is wrong

The magic hockey jersey could
predict a player's post-season GAA

Clearly, the big story in the Habs/Flyers series so far has been Carey Price. There's no nice way to say it, the kid looks very shaky right now.

That said, if the Toronto media has taught me anything it's that the Canadiens organization is smart and wise and can always be counted on to make the right move.

So don't fear, Habs fans. I have no doubt that they'll make the obvious decision, and switch to Cristobal Huet for game four.