This off-season won't compare to the summer ahead of 2016-17, when big money was handed out on several bad contracts, but there are a few deals that could be anchors in a few seasons' time.

In the days leading up to signing season, we looked at a few free agents who should be signed with caution. Chief among those, his photo front-and-center, was Wayne Simmonds. And that wasn’t without reason.

Simmonds, 30, was coming off of a tough season, a down year that ended horribly when he flopped as a deadline acquisition in Nashville and fell injured two games into the Predators’ brief playoff run. It seemed, though, that Simmonds was still the perfect player to earn an overpayment as a free agent. He’s big, he has 30-goal seasons on his resume, he can be a power play producer and he can skate up and down the lineup. Add in his leadership qualities, for which he was awarded the Mark Messier Leadership Award, and you had the right recipe for a poor signing.

So, when July 1 came and Simmonds signed a one-year, $5-million pact with the New Jersey Devils, it was a pleasant surprise. Not only was it a chance for Simmonds to go to an organization where he’ll have a shot at a consistent middle-six role, but it was a dollar figure that didn’t represent a vast overpayment. Sure, the cap hit makes it one of the 14-biggest on Day 1 of free agency, but the term is such that the deal won’t be come an anchor or a headache. If he works out in New Jersey, great. But if Simmonds fails to find his fit as a Devil, he comes off the books next summer. It’s a low-risk, high-reward situation for both sides.

Unfortunately, we can’t say the same for every deal. In fact, there were several contracts inked July 1 and beyond that could become problematic in the years to come. Here’s hoping we’re wrong, but keep an eye on these contracts in the year to come:

Semyon Varlamov, New York Islanders

The good? Varlamov is heading to an Islanders organization that is aided by the presence of Mitch Korn, the goaltending guru who just helped pull career-best performances out of Robin Lehner and Thomas Greiss. The bad? Korn is going to have to replicate that feat with Varlamov, who inked a four-year, $20-million deal with New York despite his decidedly mediocre play over the past four seasons.

There are two red flags when it comes to Varlamov. The first is his health, which has failed him repeatedly over the past several seasons. He’s suffered groin injuries, hip injuries and knee injuries over the past three seasons, and that’s worrisome for an aging goaltender. But even when Varlamov is healthy, the Islanders will have to worry about his actual ability to stop the puck. According to Natural Stat Trick, Varlamov’s goals saved above average per 60 minutes at 5-on-5 over the past three seasons (minus-0.1) is tied for 33rd among the 53 keepers who have played at least 3,000 minutes. That puts him in the same company as Jonathan Bernier, Petr Mrazek, Mike Smith and James Reimer, to name a few.

If Korn’s magic doesn’t work with Varlamov, the Islanders might rue the decision to let Lehner walk.

Tyler Myers, Vancouver Canucks

The five-year, $30-million deal Myers signed with the Canucks is much more favorable than the reported seven-year, $49-million contract the two sides were working towards. Such a deal would have made him one of the 15-highest paid rearguards in the league. Instead, Myers sits comfortably in a tie for the 22nd-highest cap hit among NHL blueliners. And based on offense alone, there’s a chance that Myers lives up to that billing. He has four 30-point seasons, five in which he’s scored nine or more goals, and he can log a lot of ice time. His career average is upwards of 22 minutes per game.

The concern, however, is whether he can shoulder the responsibility that comes along with being a top-pairing defenseman, which he will almost certainly be asked to be in Vancouver. The Canucks are thin on the blueline and Myers immediately vaults into a top-three role. His strong suit isn’t his own-zone play, and that could become a concern in short order, particularly given that his cap hit will make him difficult to move if things go sideways.

Brandon Tanev, Pittsburgh Penguins

It’s not the money so much as it is the term on Tanev’s six-year, $21-million pact that’s concerning. If it was a short-term deal for a win-now team who needed bottom-six help, the signing would make mountains of sense. He’s fresh off of a 14-goal, 29-point season, both of which were career-high totals. He can kill penalties. He’s a buzzsaw when he’s on the ice, playing with speed and physicality that is going to make him a fan and coaching staff favorite. But the term is simply too long, and anything beyond Year Three of this contract screams trade.

As it stands right now, Tanev will be the seventh-highest paid Penguins forward next season and given Alex Galchenyuk’s contract is set to expire, Tanev is currently on the books as the sixth-highest paid forward the season after next. That isn’t representative of the role he’ll play nor what he’s likely to produce. A safe bet? Tanev will be exposed come the Seattle expansion draft, and even if he's not taken, Pittsburgh will be looking to move him around the same time.

Mats Zuccarello, Minnesota Wild

Zuccarello would have been the perfect short-term addition to a team that was set to contend for the Stanley Cup next season. He was performing at his peak last season, with the second-highest goals and highest points per game rates of his career. But the reality is he’s a 31-year-old signed to a five-year deal with a $6-million cap hit by a Wild franchise that is clinging to mediocrity. Minnesota isn’t a top contender, nor are they a playoff shoo-in. And in one or two years’ time, Zuccarello is going to be entering the twilight of his career, a mid-30s skater in a young man’s game.

The issue here, too, is the no-movement clause and modified no-trade clause. He can’t be exposed in the expansion draft and the Wild will need Zuccarello to OK a move at some point in the next five years if they want to rid themselves of his contract. He can still produce and he could have a tidy 20-goal, 50-point season in 2019-20, but it might not be long before Minnesota is trying to offload the deal.

Sergei Bobrovsky, Florida Panthers

Here’s the complete list of players who inked deals with a cap hit larger than Bobrovsky’s $10-million, which he will carry over a seven-year term with the Panthers: Artemi Panarin. That’s it. One player. Granted, Bobrovsky was the cream of the goaltending crop, but he signed one of the richest free agent deals and it comes with serious boom-or-bust potential.

On one hand, Bobrovsky has two Vezina Trophies to his name and has at times looked like the best goaltender in the world. On the other, goaltending is impossible to forecast and Bobrovsky has had some significant downs to go along with his ups. The 2015-16 season, for instance, Bobrovsky had a .908 save percentage across 37 games. This past season, too, Bobrovsky only managed a .913 SP. Add to it his lack of post-season success and his career .902 SP in the playoffs and there’s reason to wonder and worry about the deal.

If Bobrovsky isn’t at least an above-average – or even a top-10 – goaltender throughout the first four years of his pact, Florida is going to have some regrets, particularly given the cap hit could handcuff the team at points in the not-too-distant future.

Want more in-depth features, analysis and an All-Access pass to the latest content? Subscribe to The Hockey News magazine.