Have the Oilers done enough to get Connor McDavid and Leon Draisaitl a Stanley Cup?
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Ryan S. Clark, NHL reporter
DALLAS — Everything about Dylan Holloway and Darnell Nurse sitting next to each other on an elevated dais at the Western Conference finals said quite a bit before either one of them answered a single question.
Between them, they represent so much of what the Edmonton Oilers have done to build around their generational superstars, Leon Draisaitl and Connor McDavid.
It’s important to have homegrown talent in today’s NHL, and the Oilers have that. They selected Nurse with the No. 7 pick in 2013 — a year before Draisaitl and two years before McDavid — which shows how long the Oilers have been trying to build through the draft. Holloway, who went 14th in 2020, is a more recent example of Edmonton remaining committed to that approach while simultaneously trying to win in the present.
“It’s cool to come in to a team with such phenomenal players,” Holloway said. “Darnell, Leo, Connor. I want to learn from those guys. They kind of paved the way here. Our team’s this good right now because of them.”
But while nine of the players in the Oilers’ Game 1 lineup were drafted and developed by the franchise, they had to build the rest of the team with intent. They acquired Warren Foegele and Zach Hyman because they needed forwards who could forecheck and score. They added Cody Ceci, Mattias Ekholm and Brett Kulak because they needed to strengthen a defense that was in a consistent state of flux.
The natural inclination could be that having superstars who have yet to hit 30, such as Draisaitl and McDavid, should guarantee a title at some point. But there are no guarantees in the Stanley Cup playoffs.
The Tampa Bay Lightning won consecutive Stanley Cups because they hit on first-rounders Victor Hedman, Steven Stamkos and Andrei Vasilevskiy while striking it rich with later-round picks Nikita Kucherov and Brayden Point. The Colorado Avalanche won their title because they were able to build around first-round picks Gabriel Landeskog, Nathan MacKinnon, Cale Makar and Mikko Rantanen.
Other teams, such as the Toronto Maple Leafs, show how building around a core of stars can come with many challenges. Despite having Auston Matthews and Mitch Marner, the Leafs have been beyond the first round only once since 2016, and there is no guarantee they’re going to win a championship with their current core.
Somewhere in the middle are the Oilers.
Since McDavid and Draisaitl first played together in 2015-16, winning the Stanley Cup has been the expectation. That only intensified once Draisaitl, who was drafted third in 2014, exploded for 50 goals and 105 points in his fourth season. His surge showed the Oilers truly had a pair of generational talents, and not just one in McDavid.
The Oilers have reached the postseason in five consecutive seasons. Altogether, they’ve missed the playoffs only twice in the McDavid-Draisaitl era. Until recently, the biggest highlight of those postseason runs came in 2022, when the Oilers reached the Western Conference finals for the first time since 2006.
If reaching the conference final in 2022 was a lesson, what they’ve done this year could determine if they’re ready to pass the final test by winning that elusive Stanley Cup.
But if they fall short, they may be a step closer toward being the latest cautionary tale of a franchise that built one of the most talented rosters of its generation and failed to win a championship.
“The organization as a whole, especially from when we first got here, has grown and grown,” Nurse said. ” At some points, when you first got here, it was like, ‘Are we ever going to even play in the playoffs?’ And now over the last few years, being a team that’s competing at this time of year is just a testament to ownership and management of where they wanted this team to grow and get to.”
The conversation about how this championship-caliber team was built starts with Oilers general manager Ken Holland bringing up two names from the team’s not-so-distant past.
The 2019-20 season was Holland’s first with the Oilers. The Oilers had several young players, with nine who were drafted by the franchise appearing in more than 20 games during that campaign. The tesm included Oscar Klefbom and Adam Larsson, who arrived in the Taylor Hall trade with the New Jersey Devils. But as Holland quickly noted, the departures of those two defensemen were the first metaphorical dominos to fall when it came to making the necessary adjustments to keep the Oilers competitive.
“Klefbom’s career was over because of his shoulder, and Adam Larsson, for personal reasons, made a decision that he didn’t want to be in Edmonton anymore,” Holland recalled. “Those are two massive pieces to try to replace. You just peck away.”
Draisaitl, McDavid, Nurse and Ryan Nugent-Hopkins are the only holdovers from that 2019-20 roster. Sam Gagner, who was drafted by the Oilers in 2007, played 36 games that season in his second stint with the club before he was traded to the Detroit Red Wings. Gagner returned for a third tour this season.
So how did Holland and his staff build out the roster? They constructed their current top defensive pairing by using the team’s 2018 first-round draft pick on Evan Bouchard, and then trading for Mattias Ekholm in 2023. It was a deal that saw them part with prospect forward Reid Schafer along with a 2023 first-round pick, a 2024 fourth-round pick and blueliner Tyson Barrie.
Holland’s 34 years with the Detroit Red Wings as an amateur scouting director, assistant GM and GM allowed him to learn something vital from former Wings GM Jim Devellano and coach Scotty Bowman: the importance of having depth players who can check, kill penalties and be trusted to play on either special teams.
“These are all the things that over 82 games are important, but over seven games are really important,” Holland said. “One miscue can change a game and change a series.”
Between Edmonton’s amateur and professional scouting staffs, Holland & Co. were able to identify the set of current NHL players who could fill those needs.
The Oilers’ professional scouting staff identified proven players who could address key needs for the club, such as Cody Ceci, Evander Kane, Brett Kulak, Derek Ryan, Foegele and Hyman, among others.
“I’ve been pretty fortunate throughout my whole career to make the playoffs, and there are some guys who’ve played a lot of games and not made the playoffs,” said Foegele, who arrived via trade in 2021. “It’s understanding that you don’t always get this opportunity. Obviously, the moves that Kenny has made — you understand what’s at stake and that everyone’s here to win.”
The prospects who became full-time roster players — such as Vincent Desharnais, Ryan McLeod, Stuart Skinner and Bouchard — were already in the system when Holland arrived, while Holloway was a pick made during Holland’s tenure.
“I think since being drafted and coming in here, they’ve kind of wanted to engrave a winning mindset,” Bouchard said. “They’ve had a lot of years prior when they didn’t have success. I think the guys here have learned from that, have built from that. They want guys coming in to know that this is a winning organization.”
As with many teams, the trick is finding the balance of using picks to build their system while knowing when to trade them to gain a useful veteran to help win right now.
The Oilers drafted 18 players in Holland’s first three years. Since then, they’ve traded away more than 20 picks and have drafted only seven players.
For example, the Ekholm trade means they don’t have Schaefer, their first-round pick in 2022, along with their 2023 first-rounder (which the Predators used to select defenseman Tanner Molendyk). They also don’t have their 2024 first-round pick because it was used in the three-team trade that brought in Sam Carrick and Adam Henrique at the trade deadline.
Past Oiler trades resulted in other teams cashing in well: The Minnesota Wild landed star defenseman Brock Faber, and the Montreal Canadiens secured defenseman Lane Hutson.
“Some have worked, some don’t … so we’ve traded away lots of futures looking at ‘this is the window,'” Holland said. “So what’s the window? You look at Connor, Leon, Darnell, Ryan. The players that were here, these are their prime years and trying to build a supporting team around them that can make us better.”
Holland said the Oilers felt good about their team. But their 2-9-1 start to this season led to the firing of coach Jay Woodcroft, who was replaced by Kris Knoblauch. The work done by Knoblauch and his staff — which includes Hall of Fame defenseman Paul Coffey — saw the Oilers go from near the bottom of the NHL standings to second in the Pacific Division by finishing 46-18-5 in their final 69 games.
That gave the Oilers the best record in the NHL since Nov. 12, 2023, when they announced they hired Knoblauch. Winning games, however, is only part of the equation. The Oilers returned to being the sort of prolific team that was averaging 3.72 goals per game, with a power play that was operating at 26.9% under Knoblauch.
They also found a way to establish a connection between their defensive structure and goaltending that hadn’t consistently been there in years past. The Oilers allowed 2.68 goals per game after Knoblauch took over, which was the fifth fewest in the NHL. Their penalty kill had a 81.7% success rate, good for seventh, while the 28 shots per game they allowed was also fifth fewest in the league.
“Everyone has had different roads to get to what our team looks like today,” Skinner said. “I think just combining all that experience and we’ve been able to grow with each other this season as well. Looking back on it, we’ve been through a lot obviously as a group. I think being able to go through what we have had to go through has brought us as a team a lot closer and we have a solid brotherhood now.”
All of their success led to a number of questions, the most significant being: Can the Oilers’ translate their regular-season success under Knoblauch to playoff success?
Beating the Los Angeles Kings in five games in the first round while fending off elimination twice to beat the Vancouver Canucks in the second round has helped answer that question. Holland said the key is having that mix of core players starting to hit their prime, with young players carving out their place alongside established veterans.
“But we also know we are in the final four, and these are the four teams that have performed the best to get to this point,” Holland said. “You’re playing the best teams in the world now. One’s going to advance, and one’s going to get shuffled to the sideline.”
The manner in which the Oilers won Game 1 of the Western Conference finals was emblematic of how they’ve tried to build a team around McDavid and Draisaitl.
Contrarians will point out that Draisaitl still scored the Oilers’ first goal, and McDavid scored the winning goal in double overtime. Those who have closely watched the Oilers will point out that the Game 1 win was a group effort.
Edmonton’s current setup meant it could rely upon a penalty kill led by Desharnais, Ekholm, Nugent-Hopkins and Ryan, among others, to blank Dallas on five attempts. Their most notable kill came just 17 seconds into overtime, when McDavid was assessed a high-sticking double minor. The Oilers’ short-handed unit took away time and space en route to running its streak of consecutive kills to 21 entering Game 3.
“I think it’s just about confidence,” said McLeod, who is part of the Oilers’ PK setup. “We’ve been tweaking it all year and we’ve found something that’s been working. It’s confidence and that everyone’s in the right spots and being aggressive, and it’s been working.”
While Bouchard and Ekholm played more than 31 minutes in Game 1, the Oilers have been able to find a balance with their six defensemen. They all played more than 20 minutes that contest, while the Stars have largely relied on five defensemen this postseason.
Prior to Game 6 against the Canucks, Skinner had a 4.63 goals-against average and a .790 save percentage this postseason. Since then, he has a 1.64 GAA and a .918 save percentage in four starts.
This postseason also shows how the Oilers are more comfortable playing in one-goal games. They’ve won six out of their 10 one-goal games, with nine of their past 11 games being decided by a single goal.
Contrast that to the prior two years, which saw the Oilers go a combined 3-6 in one-goal games. Last postseason, they had just one one-goal game in their second-round series against the Golden Knights, while having a lone one-goal game versus the Avs in the conference finals in 2022.
“You’ve got to win tight games,” McDavid said following Game 1. “We’re down to the final four teams and you don’t get to the final four without being a great team. All four teams are solid. Dallas is a great team and it’s going to be tight hockey and we’re comfortable in these games. We’re comfortable in this environment, and I thought we did a great job truthfully all game.”
Winning Game 1 of the Western Conference finals has technically made this the most successful campaign in the McDavid-Draisaitl era, considering that they were swept the last time they were at this stage in 2022.
They’re seven victories away from winning the organization’s first Stanley Cup since 1990. Only five players on the current roster were alive when Mark Messier raised the Cup that spring. In fact, Ekholm was born on the exact day when the Oilers won their last Cup which was May 24, 1990.
Capturing the Western Conference crown and then winning the Stanley Cup would bring an end to all the questions surrounding the Oilers’ strategy in building around Draisaitl and McDavid. From there, the discussion would shift to whether they could win at least one more.
Falling short of the Cup would lead to more questions in what could be an offseason of change.
The Oilers have a 10-player unrestricted free agent class. It’s a group that includes Foegele, Henrique and Desharnais. Decisions will need to be made about how to strengthen the Oilers with what CapFriendly projects to be less than $10 million in cap space.
Even that comes with questions about who would be the one charged with improving the roster; Holland is in the last year of his contract.
And if all of that isn’t enough, Draisaitl will be entering the final season of his contract, too. Whatever he decides to do will have a significant ripple effect throughout the NHL.
“Once you’ve built your team, every year is the year,” Holland said. “You’ve always got to have a look to the future. Then when the year’s over, and you haven’t won the Stanley Cup, you’re gutted. There’s an empty hole in the pit of your stomach. That’s where you have to take the summer whether you’re a player, a coach or manager and you’ve got to regroup and rebuild and play your way back into another opportunity. I think that’s certainly what we’ve done.”
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Alden Gonzalez
LOS ANGELES — It was the middle of June, the San Diego Padres were in town for what promised to be a heated series against the Los Angeles Dodgers, and Joe Musgrove, their injured ace, had one thing on his mind:
Securing a signed Clayton Kershaw jersey.
Major league players often send each other jerseys for personalization, to commemorate friendship or admiration or even milestones. But Musgrove had done that only a handful of times in his nine years as a major leaguer — all for former teammates he was once close with, never for a prominent member of the Padres’ biggest rival.
“This is the first that I’ve sent one over in admiration for what someone has done for the game,” said Musgrove, who grew up a Padres fan before ultimately pitching for the club. “I know he’s flooded with them now, and it might seem like a lot, but he’s made a big impact on this game — not only as a player, but for the way he handles himself.”
Kershaw will make his final regular-season start at Dodger Stadium on Friday, in what we now know will be one of the last appearances of his career. But even before the news of his impending retirement became official Thursday, the likelihood of it was high enough for Major League Baseball to extend him a special invitation to this year’s All-Star Game. And for a number of opposing players to seek opportunities to pay respect in their own way, whether it’s offering praise, expressing gratitude or, often, seeking autographs.
Kershaw, 37, has noticed that jersey requests have “slightly increased from years past” but stressed it’s “nothing crazy.” Sometimes a home series will go by and nobody will ask. Others, he’ll be flooded with them. “It’s like they all talk,” Kershaw said. He signs them all, either by listing his accomplishments — 3X NL Cy Young, 2014 NL MVP, 2X WS Champ! as he wrote on one for Colorado Rockies starter Kyle Freeland — or scribbling a brief message. In his mind, it wasn’t long ago that he was on the other side.
“It’s amazing how fast that flips, you know?” Kershaw told ESPN last week. “You don’t think that you’re the old guy until it happens, and then you are. It happens fast.”
WHEN KERSHAW SIGNED his fourth consecutive one-year contract with the Dodgers in March, he was considered a luxury. Blake Snell and Roki Sasaki had already been added. Yoshinobu Yamamoto and Tyler Glasnow were coming back healthy. Shohei Ohtani was on track to return as a two-way player. The likes of Emmet Sheehan, Tony Gonsolin and Dustin May were next in line.
But when Kershaw rejoined the rotation in the middle of May, in the wake of offseason knee and toe surgeries, he helped stabilize a staff that had once again absorbed an avalanche of injuries. In August, as the Dodgers’ rotation began to round into form, he found another level, winning all five of his starts while posting a 1.88 ERA. Kershaw is throwing the slowest fastball of his career, offsetting it with a slider that oftentimes lacks its traditional bite and resorting to more inventiveness than ever, even with the occasional eephus pitch. And yet his record is 10-2 and his ERA is 3.53.
“He’s making jokes about how he’s only throwing 86, 87 — and he’s still getting outs,” San Francisco Giants starter Logan Webb said. “To me that’s the most impressive thing.”
Webb was a 12-year-old in Northern California when Kershaw made his major league debut. His high school years coincided with a four-year stretch from 2011 to 2014 that saw Kershaw claim three Cy Young Awards and an MVP, accumulate 72 regular-season victories, tally 895⅓ innings and establish himself as one of the greatest of his era. Competing against him, as a fellow frontline starter on a division rival, hasn’t taken any of the shine away.
Said Webb: “He seems to amaze me every single time.”
Two months ago, Webb shared an All-Star team with Kershaw for the first time and was adamant about securing a jersey from him, even though, he said, “I usually feel awful asking guys.” On Friday, Webb will watch from the opposite dugout as Kershaw makes what might be the final Dodger Stadium appearance of his career, depending on how he factors into L.A.’s October plans.
The Dodgers boast a six-man rotation at the moment, and two of those members, Yamamoto and Snell, are basically guaranteed to start in a best-of-three wild-card series. The third spot would go to Ohtani, unless the Dodgers surprise outsiders by deploying him as a reliever. Then there’s Glasnow, who was lavished with a $130 million-plus extension to take down important starts, and Sheehan, a promising right-hander who has been effective out of the bullpen.
Kershaw wasn’t healthy enough to contribute to last year’s championship run and wants nothing more than to help with this one. But he’s also realistic.
“We’ll see,” Kershaw said. “We’ll see what happens. My job is just to pitch well. Whatever decision they make, or if I get to make a start or do whatever — they’re going to make the best decision for the team. I’ll understand either way. Obviously making it hard for them is what I want to do.”
Dodgers manager Dave Roberts doesn’t know what role Kershaw might play on a postseason roster, but he said “there’s a place for him” on it.
“The bottom line is I trust him,” Roberts said. “And for me, the postseason is about players you trust.”
ANDREW ABBOTT SAT alongside Cincinnati Reds teammate Chase Burns in Dodger Stadium’s first-base dugout on Aug. 26 and couldn’t understand what he was seeing.
“Is that a changeup?” he asked.
Kershaw famously doesn’t throw many changeups, largely because he has never been confident in his ability to do so. But suddenly Abbott was watching him uncork a pitch that traveled in the low 80s and faded away from opposing right-handed hitters, the continuation of a split-change he began to incorporate a couple years ago. To Abbott, it spoke to the ingenuity that has extended Kershaw’s effectiveness.
“He knows what he’s doing,” Abbott said. “He can just figure things out on the fly.”
The Reds’ third-year starting pitcher had shared a clubhouse with Kershaw for the first time during the All-Star Game in Atlanta this summer. He wanted so badly to pick his brain about pitch sequencing, but he also didn’t want to waste Kershaw’s time; he made small talk about their Dallas ties and left it at that.
Six weeks later, when the Reds visited Dodger Stadium, Abbott made it a point to provide a visiting clubhouse attendant with a Kershaw jersey to be sent to the other side for a signature. He already had one of Christian Yelich, who represented his first strikeout; Edwin Diaz, the brother of his former teammate, Alexis; Joey Votto, a Reds legend; and Aaron Judge, arguably the best hitter on the planet. Abbott initially didn’t want to bother Kershaw, worried that he might just be adding to an overwhelming pile, but he couldn’t run the risk of missing what might be his final opportunity.
“I watched Kersh since I was a kid,” Abbott said. “I mean, I was 9 when he debuted. I just like to have guys that I’ve watched and I’ve kind of idolized. Those are the ones I go after. It’s cool that you’re in the job with him, too.”
After spending the past four years pitching for two of their biggest rivals — first the Padres, then the Giants — Snell signed a five-year, $182 million contract with the Dodgers over the offseason and told president of baseball operations Andrew Friedman that he wanted his locker next to Kershaw’s. Snell’s locker neighbored Kershaw’s in spring training, and he now resides just two lockers down inside Dodger Stadium’s newly renovated home clubhouse.
As a fellow left-hander, Snell has tried to soak up as much as he can from watching Kershaw, specifically how he utilizes his slider. He has learned, though, that a lot of his success is driven by his mindset.
“He never gives in,” Snell said. “He’s a competitor. And you can’t, like, train that or teach that. You either have it or you don’t. And he’s very elite at competing. The game comes, and he’s the best version of himself.”
Snell arrived in the major leagues as a 23-year-old former first-round pick. But he did not believe he would stay very long, so he made it a point to gather as many personalized jerseys as he could. He already has two framed Kershaw jerseys hanging on an office wall littered with other sports memorabilia, but the end of his first year with the Dodgers has left him wondering if he has enough.
Said Snell: “I might get me another one.”
TO THOSE WHO have observed Kershaw throughout his career, the thought that he would even allow himself to be mic’d up while pitching in a game — let alone revel in it — stood as a clear indication that this would probably be it. Roberts, who managed the National League All-Stars earlier this summer, noticed a more reflective, appreciative side to Kershaw even before he took the mound for his 11th Midsummer Classic.
Roberts noticed it when Kershaw addressed his NL teammates before the game, reminding them this was an opportunity to honor those who got them there. He noticed it 13 days before that, on the night of July 2, when Kershaw finished a six-inning outing with the 3,000th strikeout of his career and spilled onto the field to acknowledge the fans. Most of all, he’s noticed it through the ease with which Kershaw seems to carry himself this season. “The edges,” Roberts said, “aren’t as hard anymore.”
“He knows he’s had a tremendous career, and I think that now he’s making it a point. He’s being intentional about taking in every moment.”
Kershaw allowed himself to savor his 3,000th strikeout — a milestone only 19 other pitchers have reached — and made a conscious effort to take in every moment at this year’s All-Star Game. His wife, Ellen, and their four children have made it a point to travel for every one of his starts this season, even when Texas schools re-started earlier this month, adding a layer of sentimentality to the stretch run of his season.
But for as much as Kershaw would like to soak in every inning remaining in his major league career, he can’t. The season keeps going, the stakes keep ratcheting up, and Kershaw believes in the link between dismissing success and maintaining an edge. “The minute you savor, the minute you think about success, you’re content,” he said. But that also means he can’t truly enjoy the end.
There’s a cruelty in that.
“Yeah,” Kershaw said, “but that’s OK. Because you want to go out competing, just like you always did. At the end of the day, being healthy, being able to compete and pitch well, being on a great team — that’s all you can ask for. If you do all of the other stuff, you become content or satisfied or whatever it is. Then it’s all downhill.”
ESPN’s Jesse Rogers contributed to this report.
BOSTON — The AL playoff race is getting tighter for the Boston Red Sox.
The Red Sox lost 5-3 to the Athletics on Thursday, dropping the three-game series to the noncontending A’s and allowing the Cleveland Guardians to crawl within 1½ games of Boston in the AL wild-card race.
The Red Sox are still in position for the third and final AL wild-card berth, but they fell 2 1/2 games behind the Yankees in the race for home-field advantage in the first round.
“We control our own destiny,” manager Alex Cora said. “We’ve got to play better baseball. That’s it. There were signs today, but we’re not there yet.”
Boston has lost five of its last seven games to turn what had been a good shot at edging the Yankees into a chance of missing out completely. Cora noted that in 2021, their last playoff appearance, the Red Sox had to rally at the end of the season.
What did he learn from that season?
“Don’t get too high. Don’t get too low,” Cora said. “It’s 162 (games) for a reason.”
The Red Sox head to Tampa Bay for three games before three more in Toronto. They finish the season with a three-game series against the Tigers at Fenway Park.
Cora insisted that there is no panic in the Boston clubhouse. On Saturday, he raised eyebrows when he responded to questions about postseason lineup construction by saying: “I think we should stop talking about October, to be honest with you.”
“There’s a lot of stuff going on and we have to play better,” he said. “I’m not saying we’re in a bad spot. But we have to wait to see if October is part of this.”
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