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10 Thoughts: Oilers coaching search, NHL trade rumours, and Stanley Cup aftermath
Carolina Hurricanes Rod Brind'Amour Stanley Cup
Photo credit: Lucas Peltier-Imagn Images
Jason Gregor
Jun 16, 2026, 16:00 EDTUpdated: Jun 16, 2026, 16:21 EDT
The 2026 season is over.
The Carolina Hurricanes are the champions, and now teams will buckle down and start preparing for next season. The NHL entry draft begins in 10 days, and free agency starts in 15 days. The first buyout window opens later tonight, and teams have 14 days to decide which players they will qualify or let walk as free agents. There is a lot happening.
Here are 10 thoughts rattling around in my head.

1. Championship coaching longevity

It is interesting to note which coaches have won Stanley Cups this decade. Jon Cooper won with Tampa Bay in 2020 and 2021. He was hired in 2013 and remains their head coach. Jared Bednar won in 2022. He was hired in August of 2016 and remains their head coach. Bruce Cassidy won his first year with Vegas in 2023. In his five previous seasons with Boston, he had compiled the second-most regular-season wins and the second-most playoff wins, including a Cup Final loss in 2019. Paul Maurice won in 2024 and 2025 with Florida in his second and third seasons coaching. Maurice resigned from the Winnipeg Jets on December 21st, 2021, feeling they needed a new voice. In the 4.5 seasons before resigning, the Jets had the ninth-best record in the NHL but could never get past the third round. Rod Brind’amour won with Carolina this season. It was his eighth season with the Hurricanes.
Cooper, Bednar and Brind’Amour are the three longest-tenured coaches in the NHL. Maurice has the second-most wins of all time, and Cassidy has the fourth-best winning percentage among coaches who have coached 800+ games.
Cooper has coached 13 full seasons with Tampa and won twice. Bednar has one Cup in 10 years, and Brind’amour has one in eight seasons with their respective teams. Most teams prefer to change coaches every three seasons, but maybe they should rethink that process. I’m not saying every coach has to last eight seasons, but the constant changing of coaches hasn’t led to much success for most teams recently.

2. Summer trade market noise

Dylan Larkin, Simon Nemec and Darnell Nurse have already asked to be traded. When I look at the top six forwards, top four defencemen and the starting goalies, I think we’ll see at least seven, likely more, traded this summer. After years with limited cap space, teams have more room, and I think some teams have so much internal pressure to win that we see some bigger names get moved this summer. Connor Hellebuyck, Mat Barzal, Jordan Kyrou, Colton Parayko, Adin Hill, Morgan Reilly, Robert Thomas, Mason McTavish, Vincent Trocheck, and Jordan Binnington are some names that have been out there in trade rumours for months. And there will be a few players not mentioned publicly that get moved. Last summer Mitch Marner, Noah Dobson, and K’Andre Miller were moved, and two of them played in the Stanley Cup final. I sense this year, due to more cap room, teams will be more open to significant trades.

3. Taylor Hall’s historic trifecta

Taylor Hall has had quite the career. On Sunday night he became the first player in NHL history to be the #1 overall pick, win the Hart Trophy and win the Stanley Cup, while reaching all three achievements with three different teams. The Oilers drafted him first overall (2010), he won the Hart with New Jersey (2018) and won the Cup with Carolina. He finished second in Conn Smythe voting. It was great seeing him hoist the Cup.

4. The Babcock investigation timeline

I had a conversation with a veteran NHL player agent yesterday discussing the Stanley Cup and other things. Near the end of the conversation, I asked him about the Oilers coaching situation and Mike Babcock.
“The opportunity to play with McDavid or Draisaitl is diminished with the potential to be coached by Babcock. It is a valid concern voiced to me by a few of my clients.”
After I tweeted the quote, I had another agent reach out expressing similar concerns. Elliotte Friedman reported the NHL has now officially started its investigation into Mike Babcock’s 2023 resignation from Columbus. It is important to note that there is nothing stopping the Oilers from hiring Babcock right now. What is unknown is whether Babcock will face further punishment after the investigation. There is no timeline on how long the investigation will take, or whether the league hands down a suspension for 10, 20, or 40-plus games. Considering how long it takes the NHL to hear an appeal for a player suspension, I would be surprised if the investigation is wrapped up before the draft. The league rarely moves quickly, so will the Oilers wait it out, or will they move in another direction?

5. The Entry Draft clock

It isn’t a must-have, but having a head coach in place by the draft is beneficial for teams. Not for the draft itself, as an NHL coach isn’t involved in amateur scouting, but more so for trade possibilities. How does the coach want the team to play? What type of players he wants, and how he views specific players, are important when discussing trades and then free agency, which opens up five days after the NHL entry draft. The clock is ticking on the Oilers and their head coaching search. The league’s investigation might force them to pivot unless the NHL has a speedy investigation that wraps up in one week. The next week will be huge for the Oilers and their search for a head coach.

6. Post-season benchmarks

Vegas has made the Stanley Cup final three times in their brief nine-year existence. Impressive. Here’s a look at the top eight teams, in terms of playoff games played in the past nine years, five years, and two years.
9 years
5 years
2 years
TEAMS 
Playoff GP
TEAMS 
Playoff GP
TEAMS 
Playoff GP
VGK
125
EDM
81
CAR
34
TBL
112
FLA
78
VGK
33
DAL
106
CAR
74
EDM
28
CAR
105
DAL
69
MTL
24
COL
98
VGK
62
DAL
24
BOS
90
COL
58
FLA
23
EDM
85
TBL
46
COL
20
FLA
84
NYR
43
MIN
17
Carolina, Vegas, Edmonton, Dallas, Florida and Colorado are in all three groups. Carolina won a Cup in its eighth year as a Cup contender. Dallas and Edmonton have yet to win. Vegas won once. The Oilers are still competitive, but their actions this off-season suggest their internal pressure to win has them incorrectly questioning how close they are. For years Carolina was unable to have any success past the second round, until this season. Credit Eric Tulsky for making smart moves to improve his team. He pivoted when Mikko Rantanen said he wouldn’t commit long-term in Carolina. He didn’t panic. He believed in their plan and found players to augment their team.
Oilers GM Stan Bowman, and arguably more importantly, owner Daryl Katz, can’t panic. Make smart moves. Find players who are committed to playing soundly defensively but who can also play fast and contribute offensively. Connor Murphy is one of those players. There are others, and they need to find them. The Oilers need to target teams who will incorrectly give up on younger players, like the Rangers did with K’Andre Miller. Miller had played five seasons and was only 20 years old, but the Rangers felt it was time to move on. There are players like that in the NHL. Bowman and company need to focus on those types of acquisitions.

7. Don’t trade Isaac Howard

I’m perplexed by suggestions the Oilers should trade Isaac Howard. Why? He had a very productive first season of pro hockey scoring 24 goals in 47 AHL games. He gained valuable experience by suiting up 29 times with the Oilers. He’s quick, skilled, and is a pure shooter. The Oilers don’t have a lot of pure shooting wingers. Matt Savoie is more of a distributor. Hyman is great in tight, but not really a shooter from the slot or flanks. Vasily Podkolzin can shoot and Kasperi Kapanen has a great shot, but he isn’t a 30-goal potential player. Good teams have different skillsets among their players, and Howard is arguably the best pure shooting winger they have. Unless you are trading him for a proven shooting winger, I’d keep him.

8. The Oilers’ restricted free agents

The Oilers have two weeks to extend qualifying offers (or sign contracts) to Spencer Stastney, Colton Dach, Connor Ungar, Owen Michaels, and Matvei Petrov. Roby Järventie has already signed in Europe, and the Oilers won’t be qualifying Josh Bloom. The only one who might not be qualified is Petrov. He hasn’t gained much traction in his three years in Bakersfield. He is only 23, but I haven’t seen much progress in his game.

9. Betting on James Hamblin

I’m most interested to see what James Hamblin does. Hamblin had an excellent season with Bakersfield. He is incredibly versatile and can chip in offensively, while also being very responsible defensively. I could see him testing the free agent market to see if he could get a better NHL chance on another organization. I believe he can be an NHL regular if given the chance, but it likely will be on a team lower in the standings, and there is nothing wrong with that. I hope he bets on himself.

10. Post-season unpredictability

What is great about the NHL playoffs is how unpredictable they are. How does Jordan Staal score six goals in the first five games of the Stanley Cup final? He is 37 years old. He’d never scored more than six goals in one entire playoff year before, but he gets hot at the most important time of the year for him and his team. No one could have predicted that, which is why the Stanley Cup remains so incredibly difficult to win. You need a good team, you need good health, and you need some luck. Sam Bennett scored 15 goals last year for Florida. Brett Howden scored 14 for Vegas this season. It happens regularly, that you need one or two players to have the greatest stretch of their life to help you win, and often those productive stretches are completely unexpected or unpredictable. It is equally exciting for the victor as it is frustrating for the vanquished.

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