<p>If there was any doubt that NHL Offseason Mode was officially activated, <a href="https://publish.dailyfaceoff.com/los-angeles-kings-acquire-kevin-fiala-from-minnesota-wild-extend-him-for-seven-years/">this week’s Kevin Fiala trade</a> signalled the start of what should be a flurry of change around the NHL. With the draft just days away and free agency less than two weeks out, which GM is currently under the most pressure to deliver for his team?</p>



<p>The <em>Daily Faceoff </em>Roundtable weighs in.</p>



<p><strong>MATT LARKIN: </strong>For me it’s&nbsp;<strong>Ken Holland</strong>. The Oilers showed real progress and potential this season, and they can’t afford to take a step backward. Will they re-sign Evander Kane? Will they find a younger goaltender to rely on as a long-term starter? Is there a chance Holland is able to place a “retired” Mike Smith on LTIR and buy out Zack Kassian, creating more breathing room to add a goaltender and re-sign Kane? Will he <a href="https://publish.dailyfaceoff.com/trade-targets-sizing-up-the-nhls-goaltending-market-this-summer/">trade one of Kailer Yamamoto or Jesse Puljujarvi</a>? Can he find a way to upgrade a D-corps on which every guy aside from Darnell Nurse seemingly plays one pair higher than he should? Have you noticed how many question marks I’ve used in this paragraph? For a team that made the conference final, the Oilers’ future is quite cloudy. The range of outcomes is incredibly wide for 2022-23. But the potential to field a true contender next year is high, too. It all comes down to how Holland plays it.</p><div class="injected-ad injected-video" data-nn-ad-tech-injection-count="0" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="229"></div>



<p><strong>MIKE MCKENNA: </strong>Externally I think Kyle Dubas has a huge amount of pressure, even though I’m not sure how much tweaking he can do to a roster that’s pretty locked in. Toronto&nbsp;hasn’t made it out of the first round in six years and Auston Matthews is inching closer to being an unrestricted free agent. And the goaltending situation is a mess right now for the Maple Leafs. But I think <strong>Brad Treliving</strong> is under the most pressure to keep the Flames at the top of the Pacific Division. Although&nbsp;Calgary fell short in playoffs, this season was a big step forward under Darryl Sutter. If Johnny Gaudreau walks, after Treliving has said the team would do everything possible to retain him, it’s not a good look. And I don’t see how the Flames would replace Gaudreau’s output on the ice. <a href="https://publish.dailyfaceoff.com/how-do-the-calgary-flames-sign-all-their-star-free-agents-this-off-season/">And he’s not the only free agent to figure out</a>. Matthew Tkachuk, Andrew Mangiapane, Oliver Kylington and more are up for new deals. The defense needs to be figured out. I think the pressure is real for Treliving.</p><div class="injected-ad" data-nn-ad-tech-injection-count="1" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="177"></div>



<p><strong>SCOTT BURNSIDE: </strong>You’d think a guy that just received a three-year contract extension would be feeling little heat. Not so with Winnipeg Jets GM Kevin Cheveldayoff, who has a monster off-season coming. First Cheveldayoff had to pivot to Plan B after Barry Trotz decided he’d take a pass on the Winnipeg head coaching job (and all others), which must have been more than a little disappointing for the Jets and their fan base. <a href="https://publish.dailyfaceoff.com/winnipeg-jets-hire-rick-bowness-as-head-coach/">He settled on veteran coach Rick Bowness </a>who appeared to be headed for retirement at age 67. That sets up the narrative, fair or not, that Bowness is just a placeholder until Trotz recharges his batteries. That’s not ideal. Cheveldayoff also has to figure out what to do with a lineup that has been in decline since reaching the Western Conference Final in 2018 and is teetering on the edge of imploding. Does Cheveldayoff trade captain Blake Wheeler and/or star forward Mark Scheifele, both of whom are under contract through 2023-24? Both options are realistic <a href="https://publish.dailyfaceoff.com/trade-targets-sizing-up-the-nhls-goaltending-market-this-summer/">although Frank Seravalli doesn’t think Scheifele is going anywhere</a>. What about the curious Pierre-Luc Dubois, whom the Jets acquired for another disgruntled forward, Patrik Laine? Dubois, a restricted free agent, has indicated he will test unrestricted free agency in two years’ time. Who does that, by the way? But do you keep the talented center if he’s got one foot out the door? And if you’re tearing apart the core of a team considered by many as recently as last season a legitimate contender do you consider moving former Vezina Trophy winner Connor Hellebuyck, who has two years left on his deal and does not possess trade protection? Or do you try and find some middle ground and keep the team tracking towards Stanley Cup contention? Pressure? Oh yes there’s pressure a plenty in ‘The Peg.’&nbsp; </p><div class="injected-ad" data-nn-ad-tech-injection-count="2" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="305"></div>



<p><strong>CHRIS GEAR: </strong>I think plenty of General Managers will be feeling the heat come October. At the top end, Florida’s Bill Zito and Carolina’s Don Waddell have to be feeling like their high-end rosters need to come through before their windows close. At the other end, Seattle’s Ron Francis needs a big offseason to rebound from a tough expansion draft, and Arizona’s Bill Armstrong has to start showing some results after two years of tanking. But I’m going to go with the league’s longest tenured GM, Nashville’s <strong>David Poile</strong>. He has had a remarkable run, in place since the franchise’s inception, but Poile’s Predators have gone to the Final only once in the team’s 23 seasons and they have now lost in the first round four seasons in a row. What’s worse, there is speculation that the team’s best forward, Filip Forsberg, may be on his way out. If Poile cannot retain Forsberg despite loads of cap space, it will be a big loss, and it will call into question what exactly the plan is in Nashville. If Poile retains (or adequately replaces) Forsberg and adds additional pieces this offseason, I think he can safely retain the title of longest-serving GM. If not, the reign may come to an end.</p><div class="injected-ad" data-nn-ad-tech-injection-count="3" data-nn-ad-tech-max-gap="130" data-nn-ad-tech-current-gap="210"></div>



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