Phil Kessel appears to be the kind of winger the Penguins have been pining for. (USATSI)
Phil Kessel appears to be the kind of winger the Penguins have been pining for. (USATSI)

It’s that time of year when a lot of players find their ways to new teams. This offseason, it’s been through a mess of high-profile trades and the usual free agent movement. However, just because a player moves on to another team doesn’t mean the move always makes sense for either party.

We’ve seen it time and time again where a player comes into a team with nothing but optimsim on his side. Then that player gets on the ice in the fall and disappointment reigns supreme. The fall is still a long time away, though. 

So here’s a look at which players changing addresses this offseason appear to be the best fit for their new organizations, as well as a few that we’re a little more cautious about.

Best fits

1. Phil Kessel, Pittsburgh Penguins: This is one of those trades that probably couldn’t have worked out better for the player or his new team. The Penguins have desperately needed an elite winger for either Sidney Crosby or Evgeni Malkin and they have it in Kessel. The player meanwhile desperately needed to go to a market where he wouldn’t have to be the guy. Regardless of which line Kessel plays on, he gets an elite center essentially for the first time in his career. Sure, there is risk that Kessel doesn’t mesh well with whichever of Pittsburgh’s stars he ends up playing with, but that seems unlikely. Because of Crosby and Malkin, the Pens always have two lines that can give the opposition trouble. By adding Kessel, they have at least one line that could devastate the opposition.

2. Dougie Hamilton, Calgary Flames: The shock that this trade actually happened still hasn’t worn off yet. The Flames have already made a significant commitment to Hamilton with his new six-year deal, but this deal is going to work extremely well in the short-term, too. The Flames now boast one of the better defensive units in the NHL. Each of the Flames top two defensemen – Mark Giordano and T.J. Brodie – are left shots. Hamilton is a righty, and gives the Flames one true No. 1 D (Giordano) and two guys with No. 1 potential (Brodie and Hamilton). That’s an incredible situation to be in. Additionally, Hamilton might be a better fit organizationally here. There were the rumors about Hamilton’s time in Boston, as there seems to be with most Bruins traded away, but he’s insulated better in Calgary. There's a little more time for him to grow into whatever it is the Flames need him to be in the longer term. He could also be a safety net for the club in the event they fail to re-sign Giordano, whose contract expires after 2015-16.

3. Andrej Sekera, Edmonton Oilers: The Oilers had a lot of issues to contend with last season, but the blue line was a big one. Going out and getting Sekera, one of the top defensemen available in free agency, was a huge boost to that defensive unit. Edmonton still has to make some moves. One of Andrew Ference or Nikita Nikitin could be on the way out one way or another, but Sekera is a nice, steady veteran who probably ends up providing an upgrade after Jeff Petry was traded away last season.  Over the last two years in particular, Sekera has made his teams better when he’s on the ice, and that includes a Hurricanes squad that struggled mightily. Also, having had the experience as a No. 1 with Carolina, he should transition easily into that role in Edmonton. The Oilers need reliable veterans intertwined with their youth movement and Sekera appears to be the right kind of player to fit in.

4. T.J. Oshie, Washington Capitals: The St. Louis Blues’ cap-crunch loss is probably going to be the Capitals’ top-six gain. Oshie of course rose to prominence during the 2014 Winter Olympics, but more importantly he’s also coming off of two of his best seasons in the NHL. He had a career year in 2013-14 with 21 goals and 60 points, before following that up with 55 points last season. The Caps lost multiple veterans like Troy Brouwer and Joel Ward this offseason (the former in the Oshie trade), but gained a true top-six winger in the process. Oshie is an upgrade over what they had, even if the Caps still need to replace some bodies. Then you throw in a potential breakout from Evgeny Kuznetsov and/or Andre Burakovsky and the Caps look to be a team built with more skill in 2015-16 than they had last season. Oshie is no slouch defensively, either, and could get even better under Barry Trotz in that department.

5. Ryan O’Reilly, Buffalo Sabres: The big contract on top of a fairly sizable trade package to acquire O’Reilly puts instant pressure on the player, but there are a lot of reasons for optimism in Buffalo. The building blocks the team has in place such as draftees Jack Eichel and Sam Reinhart, plus the additions from last season in a trade – Evander Kane and Zach Bogosian – all helped turn the tide. Bringing O’Reilly into the fold took things to another level. How many 24-year-olds can come into a team with 427 NHL games under their belts? Not only that, but one that has 119 points over the last two seasons. O’Reilly can be a center or a wing, plays a strong two-way game and brings a consistent effort level to the ice. Finding players at his age, with his experience and recent success is rare. That’s why he’s so expensive, but that’s also why he’s a great fit for a team ready to transition from rebuilding to competing again.

Wait and see

Brandon Saad, Columbus Blue Jackets: The Blue Jackets are betting big on Saad and it’s probably a good bet. Columbus needed to bolster its top six and Saad gives them a two-way forward that can really be a Swiss Army knife for them. However, the caution here is that Saad spent the bulk of his young career playing alongside stars Jonathan Toews and Marian Hossa, a pair of likely Hall of Famers. He won’t have that in Columbus, so there's some cause for concern about production rates. There's nothing wrong with a little cautious optimism considering Saad's age, physical strength and the fact he's noticeably grown in each of his first three full seasons in the league.

Artem Anisimov, Chicago Blackhawks: A big reason the Blackhawks were comfortable in dealing Saad is that they felt they were getting the No. 2 center they’ve been in a perpetual search for with Anisimov. Chicago has so much belief that they extended Anisimov with a five-year deal. The Hawks have not really had anyone like him in the No. 2 center role and Anisimov has never had the types of players on his wings like the ones he’ll likely see time with in Chicago. Anisimov's career has been up and down, though, and he was limited to 52 games last season due to injury. Is he a safe bet? No, but given the circumstances surrounding the trade, he's an intriguing addition.

It’s never too early

Connor McDavid/Jack Eichel: Neither has played a single NHL game yet, but just by the way each has changed the entire demeanor of their respective fanbases, the honeymoon should last a while for these two top prospects. McDavid posted five goals in a rookie camp scrimmage, which wouldn’t necessarily be noteworthy if everything he did on the ice didn’t make you drool from your brain just plain quitting. He does some ridiculous things with the puck and there might not be a skater like him in the NHL right now. Then Eichel has been everything the Sabres have needed him to be. He toured Buffalo and showed off a star quality and easiness while interacting with fans. The Sabres need an ambassador of optimism and Eichel is that. The Sabres rookie scrimmage is Friday, so hopefully Sabres fans don’t freak out if Eichel doesn’t score six. Either way, these two guys are going to be a lot of fun to watch next year, whether you’re a fan of their teams or not.