It takes only one productive phone call to steer a contract negotiation toward a resolution, though. So, theoretically, all five RFA holdouts could be ready for opening night in early October. However, there's a good chance one or two of the situations will still be at an impasse.
Based on reports, Laine seems most likely to follow William Nylander's lead. Last year, Nylander signed with the Toronto Maple Leafs literally minutes before the Dec. 1 deadline, and there's no reason to believe Laine won't entertain a similar wait-and-see strategy, as his camp and the Jets aren't on the same page.
Winnipeg has the most to lose here. Not only do the Jets have multiple RFAs unsigned, but they're also shorthanded in general. Jacob Trouba and Tyler Myers are playing elsewhere and Dustin Byfuglien is on a leave of absence. It could be a full-blown crisis soon in Manitoba if these holdouts drag into the season.
Is this the year the Penguins hit a fork in the road?
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The 2018-19 season was not a pretty one for the Pittsburgh Penguins. While a 100-point campaign would appear positive, the Penguins' was filled with distractions - mainly the feud between now-departed Phil Kessel and head coach Mike Sullivan - and ended with a surprising first-round sweep at the hands of the New York Islanders.
Time is running out for Pittsburgh's veteran core, and the Penguins need a bounce-back year from Evgeni Malkin to have any shot at making a deep playoff run.
There are other questions to be answered, too. Can Alex Galchenyuk live up to his potential? Is the defense - specifically, the third pairing of Jack Johnson and Erik Gudbranson - too slow for today's NHL? Will the head-scratching six-year, $21-million deal handed to Brandon Tanev bear fruit?
This team's ceiling is another Stanley Cup, but it's easy to see how things could go sideways.
Who will have a better rookie season: Hughes, Kakko, or Makar?
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Good luck predicting the Calder Trophy race.
Jack Hughes, Kaapo Kakko, and Cale Makar - the marquee names of the incoming rookie class - are all built for the modern game. Hughes is Connor McDavid lite down the middle, Kakko is a goal-scoring force of nature on the wing, and Makar is a rover-type blue-liner with wheels. There's little doubt about their skill sets and potential.
On the surface, Makar has the upper hand in the Calder conversation thanks to a 10-game stint with the Avalanche during the 2018-19 playoffs. But Hughes' preseason highlight reel and Kakko's NHL readiness should give prognosticators pause. Regardless, expect an immediate impact from all three.
What has to go right for the Oilers to make playoffs?
Jamie Sabau / Getty Images
In short, everything.
Starting in the crease, Mikko Koskinen and Mike Smith need to push each other. The Edmonton Oilers don't necessarily need one to grab the job and run with it, but the pair should trade hot stretches enough throughout the year so the team doesn't go into a lull for 10 to 15 games.
On the blue line, Oscar Klefbom and Adam Larsson need to regain their 2016-17 form. Klefbom has battled injuries over the last two years and Larsson had to deal with the death of his father. Both blue-liners need to be at their best. Additionally, Darnell Nurse needs to continue to make strides.
Up front, it's basically a given that McDavid and Leon Draisaitl will do their thing, but what about the rest? It's a tall task, but if Edmonton's other three lines can break even in more games than not, the Oilers have a shot at the postseason. That's a giant "if," though.
Whose offseason will prove most worthwhile: Rangers, Panthers, or Devils?
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On aggregate, the Eastern Conference stole the show this summer. Specifically, two teams in the Metropolitan and one in the Atlantic did.
Free agency's biggest catches, Artemi Panarin and Sergei Bobrovsky, settled in with the New York Rangers and Florida Panthers, respectively. Legendary coach Joel Quenneville signed on to coach Bobrovsky and the upstart Panthers. P.K. Subban landed with the New Jersey Devils in a draft-weekend trade. And Hughes and Kakko were scooped up by the Devils and Rangers, respectively, the day before.
On paper, they're all better. What's not so clear is which of these franchises will benefit from these moves the most over the course of the season.
Do the Blackhawks have a second wind with Kane and Toews?
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The Chicago Blackhawks have missed the playoffs in back-to-back campaigns and haven't won a postseason series since their Stanley Cup triumph in 2015. Last season was a transition year. Quenneville was fired after 15 games and the team took some time adjusting to Jeremy Colliton, going 3-13-1 in the young coach's first 17 contests.
Eventually, things started to click.
The offense worked its way into a groove, the power play became lethal, and the club finished the season on a 27-18-8 run. Jonathan Toews, Patrick Kane, and several others had career-best offensive seasons, but goal prevention was still an issue. This was addressed in the offseason, though.
Vezina finalist Robin Lehner was signed in free agency to give the club a potent one-two punch in goal when Corey Crawford is healthy, which wasn't the case for a large chunk of last season. And while they weren't sexy additions, modest upgrades were made to the blue line in the form of Calvin de Haan and Olli Maatta.
If the Blackhawks can tighten up defensively, this team could make some noise again as Kane and Toews continue to play at a high level.
Can Kessel help Coyotes snap playoff drought?
Norm Hall / Getty Images
The Arizona Coyotes' leading scorer last year was - wait for it - Brad Richardson, who had 15 goals. General manager John Chayka had a serious problem on his hands, but the offseason acquisition of Phil Kessel was certainly a step in the right direction.
Will Kessel and his 30-to-40 goals be enough? The Coyotes haven't made the playoffs since 2011-12 and, while a clean bill of health would go a long way, aren't locked into a spot this year, either.
Coach Rick Tocchet's most dangerous forwards include Kessel, Clayton Keller, and Derek Stepan. A solid trio, sure, but not exactly a murderers' row. Goaltending and defense have been the club's strengths over the past few seasons, and those groups will be relied upon once again to lead the charge in 2019-20.
The NHL is in a better spot when all of its teams are competitive. Lengthy playoff droughts - Arizona's is up to seven years - in a standings system that promotes parity are a bad look, and it's a dynamic that stunts the sport's growth in certain areas of North America.
How good can Binnington be?
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He's now a hero in St. Louis, but Jordan Binnington is still a bit of a wild card entering the season. He started last year by putting up historically great numbers before coming back down to earth in the latter stages, despite doing all he needed to do to win a Stanley Cup.
Stat
1st 18 starts
Next 12 starts
Playoffs
Rec.
15-2-1
9-3-0
16-10
GAA
1.49
2.36
2.46
SV%
.942
.912
.914
SO
5
0
1
Which Binnington will the Blues get over the course of a full season? And when he struggles for the first time at the NHL level, how will he respond?
By all indications, Binnington is as cool as a cucumber and will be able to handle any adversity thrown his way. However, he's more likely to settle into the .910-to-.915 save percentage range than he is to become one of the league's elite goaltenders. His ceiling is yet to be determined, though.
Will the Lightning be haunted by early playoff exit?
Jamie Sabau / Getty Images
Having a historically successful regular season ultimately meant squat. Shockingly, the 2018-19 Lightning (62-16-4) were swept in the first round of the playoffs.
The Lightning could again destroy virtually everything in their path from October to April. Nobody would be surprised if an incredibly deep team led by Nikita Kucherov, Victor Hedman, and Andrei Vasilevskiy racks up 120-plus points for the second year in a row.
From Game 1 onwards, though, the postseason will be hanging over the organization's head. Will we look back on last year's sweep to the Columbus Blue Jackets and ultimately chalk it up to a powerhouse having one bad week at the worst possible time, or will we come to realize there's something about the makeup of this roster that's preventing it from finding success in the playoffs?
Will a Canadian team finally win the Cup?
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It's a question that's been asked every season for over 20 years, but we have to bring it up again. Can a team bring the Stanley Cup to Canada?
This year's prospects are quite bleak. The Toronto Maple Leafs provide the best hope, and the Flames aren't too far behind. After that? Canada will be lucky to have a third team even make the playoffs.
The Jets are spiraling downhill, the Oilers likely haven't done enough to build around McDavid, and the Vancouver Canucks are trending in the right direction but may be another year away from making the playoffs. The Montreal Canadiens are good, but probably not good enough in a deep division, and the Ottawa Senators are in the infancy stages of a rebuild.
Current broadcaster and former star NHL forward Jeremy Roenick weighed in on current contracts in the league and implied they're being handed out to players who have yet to earn them.
Former NHL pest Matthew Barnaby chimed in to make another sweeping generalization about the difference between the modern game and that of their era.
Outspoken agent Allan Walsh responded to Roenick's tweet with some rather pointed criticism.
Roenick made $53,835,000 in total base salary during his 20-year NHL tenure, including a combined $33.94 million from 2001-02 through 2005-06, during which he scored 76 goals in 274 games - an average of 19 goals over the four campaigns.
Marner, who was also a restricted free-agent winger following his third NHL season, signed a six-year, $65.36-million pact with the Leafs last week. The deal carries an average annual value of $10.89 million.
The Avalanche made Rantanen a long-term offer earlier in September but negotiations have not progressed much since then, LeBrun adds.
Rantanen's agent, Mike Liut, said Wednesday he is "not close" to landing a new deal for his client.
The 22-year-old finished second in team scoring with the Avalanche last season, setting career highs with 31 goals and 87 points in 74 contests. Here's how the towering Finn's numbers stack up to Marner's through each player's first three NHL campaigns:
Player
GP
G
A
Pts (per game)
ATOI
Marner
241
67
157
224 (0.93)
17:41
Rantanen
239
80
129
209 (0.87)
18:53
Rantanen is currently skating with the Storhamar Dragons in Norway as he awaits a resolution to his contract dispute. The 6-foot-4 forward remains on the list of blue-chip restricted free agents who are still unsigned. Brayden Point, Matthew Tkachuk, Patrik Laine, and Kyle Connor are all awaiting new deals with their respective clubs as well.
Colorado holds a projected $15.61 million in cap space with Rantanen the only remaining player without a deal, according to CapFriendly.
The Ottawa Senators have signed defenseman Thomas Chabot to an eight-year contract extention with an average annual value of $8 million, the team announced Thursday.
There's no shortage of bench bosses who will begin 2019-20 feeling the heat.
Whether they guide a team on the rise that hasn't gone deep enough, a franchise that's stuck in the mud, or a historically great regular-season club that hasn't achieved Stanley Cup glory, these leaders will need to meet expectations in the upcoming campaign to stave off a potential pink slip.
Paul Maurice, Jets
Hired: January 12, 2014
Expectations were high for the Winnipeg Jets after they reached the Western Conference Final in 2018, but last season was unquestionably a disappointment, as the Jets were bounced from the first round of the playoffs by the eventual NHL champion St. Louis Blues.
Maurice's club faltered down the stretch, dropping six of its final nine regular-season contests before the six-game loss to St. Louis. And while the coach remains well-respected across the league, rumors of discord in the Winnipeg dressing room dogged his team in the latter half of the campaign.
Given the amount of skill on the Jets' roster, Maurice's job will continue to be heavily scrutinized, and he's not alone, as general manager Kevin Cheveldayoff could also be on the hot seat - particularly if the Patrik Laine and Kyle Connor negotiations drag into the season.
Mike Babcock, Maple Leafs
Icon Sportswire / Icon Sportswire / Getty
Hired: May 20, 2015
Speaking of scrutiny, there aren't many markets with more of it than Toronto.
Babcock tempered expectations when he joined the Maple Leafs by saying "there's pain coming," and he was right at the time, as the team was still rebuilding. However, the pressure to make progress after three consecutive first-round exits is now mounting on the veteran head coach and his charges, particularly after Mitch Marner's new six-year deal was agreed upon last week.
The Leafs' core forwards are now locked up long term, but goaltender Frederik Andersen is under contract for just two more seasons, so the club's window to take a significant step forward may not be as large as it seems - and Babcock surely knows it.
While Toronto GM Kyle Dubas publicly committed to Babcock in May, the bench boss has come under fire for his deployment decisions - particularly regarding Auston Matthews' ice time - and while those two talked over the summer, all three will need to be on the same page this season or Babcock could find himself in the figurative crosshairs.
Claude Julien, Canadiens
Bruce Bennett / Getty Images Sport / Getty
Hired: February 14, 2017
Montreal is another high-pressure market, and while Julien is entering only his third full season in his second stint behind the Canadiens' bench, a third straight campaign without a playoff berth could put his job in jeopardy once again.
The 59-year-old guided the club into the postseason in 2016-17 after being hired to replace Michel Therrien for a second time, but the team has been unable to return to the playoffs since then, missing out by two points last spring.
General manager Marc Bergevin would also be on the hot seat if the Canadiens fail to qualify, but Julien is more vulnerable because Bergevin and Montreal's ownership control his destiny and have shown they're willing to make a coaching change during the season.
Expectations for this club aren't sky-high, but they're always a little higher in Montreal than they might be in some of the NHL's other cities. Having been fired by the Canadiens once before, Julien is certainly aware of that fact.
Bruce Boudreau, Wild
Hired: May 7, 2016
Bruce Kluckhohn / National Hockey League / Getty
Boudreau has two major factors working against him as 2019-20 draws near.
First, like Babcock, Boudreau has failed to guide his club beyond the first round. Under his guidance, the Minnesota Wild missed the playoffs last season following two consecutive defeats in the opening round (they also lost in Round 1 the year before Boudreau came aboard).
Second, the Wild have a new GM in Bill Guerin, who replaced Paul Fenton after only one season at the helm.
General managers often prefer to bring in their own head coach, but even if Guerin sticks with Boudreau, the 64-year-old bench boss will presumably be on a short leash given the club's mediocrity in recent years. It doesn't help that Fenton's questionable roster moves have put Boudreau at even more of a disadvantage.
Jon Cooper, Lightning
Icon Sportswire / Icon Sportswire / Getty
Hired: March 25, 2013
Cooper isn't under as much pressure as the other coaches on this list, but he could be feeling the heat if the Tampa Bay Lightning suffer another early postseason exit.
The 52-year-old Cooper was named a finalist for the Jack Adams Award in 2018-19, and rightfully so following the Lightning's historically dominant regular season. However, Tampa Bay's stunning first-round exit by way of a sweep at the hands of the Columbus Blue Jackets cut their remarkable campaign short and left many on the losing side searching for answers.
Tampa Bay has reached a Stanley Cup Final and made two trips to the Eastern Conference Final under Cooper, but another premature conclusion to a campaign will put his job at risk regardless of how well his squad performs over the 82-game schedule.