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The five most regrettable free agent signings of the past season

Sometimes the best money is money not spent, and a few NHL GMs learned that lesson the hard way last summer by making some misguided moves in free agency that ended up hurting more than they helped either on-ice or on the balance sheet. And you’ll find five such free agent signings below.

Now, keep in mind, the following list of signings includes any deal that was struck after the culmination of the 2016-17 regular season. So, any deal inked beyond April 10, 2017, is fair game. With that in mind, here are the five most regrettable deals inked last off-season:

If you’re looking for a complete list of free agents who signed deals with cap hits greater than Hanzal’s on the opening day of free agency last season, you’ll be left looking for quite a while. In fact, it took two whole days until the Stars inked Alexander Radulov — admittedly one of the better summer signings — for any UFA’s deal to exceed the $4.75-million AAV attached to Hanzal’s contract. And while we can make some excuses for Hanzal’s five-goal, 10-point season, the reality is that even in the 38 games he did play last season, he was utilized as nothing more than a third- or fourth-line pivot. To quote Mad Men’s Pete Campbell, “Not great, Bob.”

The good news is there’s plenty of room for Hanzal to make the deal look much better under new Dallas coach Jim Montgomery, and if the 31-year-old center can stay healthy next season, there’s a good chance he gets back to his 30- to 40-point ways. Right now, though, it has to be a tough cap hit for Stars fans to stomach.

Elliott, 32, was coming off of a down year and an incredibly disappointing year as the Flames No. 1 netminder in 2016-17, one in which he — no pun intended — flamed out of the Calgary crease with an ugly playoff performance. It was so bad that he ended his time with the organization watching from the bench, pulled less than six minutes into his final game as a Flame as the Anaheim Ducks completed a playoff sweep. Oof.

There was reason to believe Elliott could bounce back, though. He was only one season removed from posting a league-best .930 save percentage and, even including his down year in Calgary, boasted a solid .921 SP over his past six seasons. But one bad year with the Flames was followed by another ugly one with the Flyers. Elliott ended up splitting time and posting a .909 SP in 43 appearances, following that up with an unsightly .856 SP in the post-season. He still has one year at $2.75 million left on the two-year deal he signed last summer.

The Penguins basically erased this signing from their cap, which should tell you about all you need to know. Less than one year after inking the deal, Pittsburgh shipped Hunwick along with Conor Sheary, who was another money-misfire by GM Jim Rutherford last summer, off to the Buffalo Sabres and got only a conditional fourth-round pick in return. Not exactly a big prize for two NHL-calibre players.

The unfortunate reality with Hunwick in Pittsburgh is that he simply didn’t fit into the system. The then-32-year-old was coming off of two solid if not spectacular years with the Toronto Maple Leafs, with whom he scored three goals and 29 points while averaging 20 minute across 132 games played, and it was believed he could slot into the Penguins’ D-corps and bring some added depth. Instead, he ended up watching nearly half the season from the press box before sitting out every single game of the playoffs as a healthy scratch. That wasn’t the hope when the Penguins signed him to a three-year, $6.75-million contract.

Acquiring Darling from the Chicago Blackhawks ahead of July 1 with the intention of signing him to push for the starting job didn’t raise any red flags in Carolina. What did, though, was inking the 28-year-old netminder, who had 75 games NHL experience in a primarily backup role on a Stanley Cup-contending team, to a four-year pact worth $16.6 million. For those scoring at home, that’s a $4.15-million cap hit for a relatively unproven netminder and a statement signing that told the rest of the league that Darling was Carolina’s guy in goal.

True as it may be that there wasn’t a single soul rooting against Darling, who was a fantastic success story in Chicago, his first campaign as a No. 1 didn’t quite go as planned, to the point there were questions whether he would be back at all this coming campaign. It has been confirmed at this point that he will be back, but his .888 SP and bloated 3.10 GAA in 43 games last season will mean he has a short leash this time around. And if he doesn’t find his form, the Hurricanes are going to have a tough time off-loading the final two-plus seasons of his deal.

The creme de la creme of misfires last off-season comes from the Vegas Golden Knights, who seemingly did everything else right en route to powering their way through the Western Conference and into the Stanley Cup final in their inaugural season. Signing the 30-year-old Shipachyov was seen as a coup for the expansion Golden Knights given his outstanding KHL performance, but the deal ended up being a dud from the outset. Vegas wanted to send Shipachyov to the minors, he didn’t want to go and the entire thing became a mess.

The end result was that Shipachyov decided he didn’t want any part of the Golden Knights anymore and wanted to head back to SKA St. Petersburg, with whom he had spent the season leading up to inking his two-year, $9-million deal with Vegas. He ended with his contract terminated, paid back all but $86,000 of the $2-million signing bonus he received from the Golden Knights and when all was said and done, the Russian center ended his NHL career — that’s right, retired — with three games played and one goal.

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