Shortly after losing Game 7 of the Stanley Cup Final back in June, the Edmonton Oilers quietly let general manager Ken Holland walk out the door. The old vacuum salesman’s five-year contract reached its end and the organization decided it was time to move on.

Holland’s Hall of Fame front office career will mostly be remembered for his time with the Detroit Red Wings, in which he helped to build and maintain a team that won four Stanley Cups between 1997 and 2008. What about his time with the Oilers?

Holland didn’t deliver on his plan to bring a Stanley Cup to Edmonton but he put together a band around Connor McDavid and Leon Draisaitl that was good enough to come just one win away from reaching the goal. Depending on who you ask, though, there’ll be many varying takes on how much credit the veteran deserves for the team’s success.

In this two-part series, we’ll look back at Holland’s five seasons with the Oilers and discuss how he should be remembered in Edmonton.

Following a 3-2 loss to the Red Wings in late January of 2019, the Oilers fired general manager Peter Chiarelli. The team fell to 23-24-3 on the season with that loss and they were well on their way to missing the playoffs for the second year in a row.

Struggling to ice even a middling team by the fourth season of Connor McDavid’s career was far from ideal and things had to turn around quickly. The Oilers lacked quality forward depth behind their stars, they had a thin blueline in front of inconsistent goaltending, and the team was mired in salary cap hell.

Ken Holland was pitched on being the one to clean up Chiarelli’s mess that night in Edmonton and he was officially introduced as president and general manager a few months later in May. His time in Detroit ultimately began to end when Red Wings legend Steve Yzerman left a very successful Tampa Bay Lightning team with an eye on returning to his former club.

There wasn’t a tremendous amount of fanfare about Holland taking over in Edmonton, considering how the Red Wings had been performing. Detroit had seen their 25-year playoff streak end a couple of years earlier and they ultimately chose to enter a much-needed rebuild by going in a new direction. Much of Holland’s success with the Wings came during the free-spending era of the late 90s and early 2000s and it was a different story with the salary cap in place.

The biggest move of the summer came out of the blue in the middle of July. The Oilers traded Milan Lucic to the Calgary Flames in exchange for James Neal. Both players were expensive and underachieving but Neal’s contract wasn’t buyout-proof like Lucic’s salary structure. This swap was the first clear win fans in Edmonton had seen made by a general manager in quite some time and it earned Holland respect from skeptical observers.

The Oilers came flying out of the gate in 2019-20 with five consecutive wins and they boasted a 9-4-1 record by the end of October, which was a much better start than in previous seasons. Adding to the excitement in Edmonton was the fact that two former Calgary Flames were leading the way for the Oilers. Over the first month of the season, James Neal scored 11 goals in 14 games and Mike Smith posted a .919 save percentage in eight starts.

While the Oilers still struggled to outscore opponents without McDavid or Draisaitl on the ice at even-strength, the team produced significant improvements on special teams. After having a putrid 74.8 penalty kill percentage in 2018-19, the Oilers posted the second-best penalty kill in the league in 2019-20 at 84.4 percent. Their power play also improved from 21.2 percent to a league-best 29.5 percent.

The team slowed down in November and struggled through December but turned things around in January to remain in a playoff spot when the trade deadline rolled around in February. Holland acquired Edmonton native Tyler Ennis from the Ottawa Senators for a fifth-round pick and added puck-moving defenceman Mike Green from the Red Wings for a conditional fourth. He then made another deal with his former club, which saw Edmonton send two second-round picks and Sam Gagner to Detroit for speedy winger Andreas Athanasiou.

Before making those trades, Holland also did some housekeeping work. Having found success playing alongside Connor McDavid on the top line, rugged winger Zack Kassian agreed to a four-year, $12.8 million contract extension. A couple of weeks later, pending restricted free agent defenceman Darnell Nurse signed a two-year extension worth $5.6 million annually.

When March rolled around, Edmonton appeared poised to clinch a playoff spot for the first time in three years. The team did wind up in the post-season, just not like how anybody expected.

The league was paused in the middle of March because of the COVID-19 pandemic and play didn’t resume until August, with 24 teams playing in no-contact bubbles without fans between Edmonton and Toronto. The Oilers were in fifth place in the Western Conference with a 37-25-9 record when the season was stopped, so they matched up in a five-game play-in series against the Chicago Blackhawks, who squeezed into the expanded field with a 32-30-8 record.

On paper, this series looked like nothing more than a warmup for the Oilers, but the experienced Hawks took them down in four games. It was a disappointing end to what had been a very encouraging season.

The pandemic had ramifications on the NHL that were felt for years to come. Losing all of the gate money from the missed chunk of the regular season, along with having the playoffs played without fans, resulted in the league coming up well below revenue targets for the year. As a result, the salary cap ceiling saw only a $2 million rise from the 2019-20 figure of $81.5 million over the following four seasons.

Already in a tight cap situation, Holland had less flexibility than expected in the off-season ahead of 2020-21. He opted not to tender a contract to Athanasiou as a restricted free agent because the newly acquired winger was eligible for arbitration and would have been able to earn a raise on his $3 million annual salary.

The Oilers re-signed Ennis and Smith to one-year deals and added Kyle Turris, Devin Shore, Dominik Kahun, Tyson Barrie, and Slater Koekkoek in free agency. Holland was also able to get disgruntled top prospect Jesse Puljujarvi to agree to a two-year contract with the Oilers after spending the 2019-20 season playing in Finland.

Because of pandemic border restrictions, all of the Canadian NHL teams were put in one division together for a shortened 56-game season in 2021. With an absurd 105 points, McDavid led the Oilers to a 35-19-2 record, good for second place in the Canadian Division. Despite the team cruising to a playoff spot in a fairly soft division, Holland had a quiet trade deadline, opting only to add veteran defenceman Dmitry Kulikov from the New Jersey Devils for a fourth-round pick.

The Oilers matched up against the Winnipeg Jets in the first round, a team that Edmonton had beaten in seven of nine meetings during the regular season. The difference come playoff time was Connor Hellebuyck, who posted a .950 save percentage in the series. The Jets took Game 1 by a score of 4-1 and then proceeded to win the next three games in overtime, capped off by a triple-overtime victory in Game 4.

It was another playoff letdown following an encouraging regular season for Edmonton, but the subsequent off-season offered Holland his first real opportunity to make major additions to the team’s roster. The Oilers bought out James Neal, lost Adam Larsson in the expansion draft, and had a few players leave as free agents, giving Holland about $20 million in cap room to work with.

The Summer of Ken began when the Oilers re-signed impending free agent Ryan Nugent-Hopkins to an eight-year, $41 million contract extension. The first addition that Holland made that off-season came shortly before the draft when the team traded Caleb Jones and a third-round pick to the Blackhawks for veteran defender Duncan Keith, who had requested a trade from Chicago to be closer to his family in British Columbia.

When free agency opened later in the month, the Oilers signed Zach Hyman, Cody Ceci, and Derek Ryan and added Warren Foegele in a trade with the Carolina Hurricanes. Throughout the rest of the summer, Holland signed the team’s restricted free agents and came to terms on an eight-year, $74 million contract extension with Darnell Nurse, who was set to enter the second season of the bridge deal that he signed during the 2019-20 season.

The new-look Oilers came flying out of the gate in 2021-22, just like they did in Holland’s first season with Edmonton a couple of years earlier. They started the year with a five-game winning streak and owned a 15-5-0 record at the beginning of December.

The team battled through injury and illness during the winter months and fell down the standings because of six- and seven-game losing streaks. After coming out of the All-Star break with hapless losses to the Vegas Golden Knights and Chicago Blackhawks on back-to-back nights, the Oilers fired head coach Dave Tippett and assistant coach Jim Playfair. It was the first time in Holland’s career that he had fired a coach mid-season.

Jay Woodcroft and Dave Manson were brought up from the team’s American Hockey League affiliate to take over behind the bench in Edmonton and the Oilers immediately responded with a five-game winning streak. The Oilers had a 23-18-3 record when Tippett was fired and went 26-9-3 the rest of the way with Woodcroft for a 49-27-6 finish, the team’s most wins in a season since the 1980s.

Holland’s biggest addition during the season came after Evander Kane had his contract terminated by the San Jose Sharks in January. The Oilers scooped up the power forward on a one-year deal and he scored 22 goals and 39 points over 43 games in the second half of the season. Ahead of the trade deadline, Holland moved William Lagesson and a second-round pick to acquire Brett Kulak and traded a fourth-round pick for Derick Brassard.

Edmonton matched up with the L.A. Kings in the first round of the playoffs and edged them out in a tight seven-game battle. In the second round, the Oilers faced the Calgary Flames, who had the best record in the Pacific Division at 50-21-1. The Flames took Game 1 with a wild 9-6 victory and then the Oilers stormed back and won the series with four consecutive wins, capped off by an overtime winner from McDavid in Game 5.

The Oilers advanced to the Western Conference Final for the first time since their run to the Stanley Cup Final in 2005-06. They went up against the 56-19-7 Colorado Avalanche and were swept aside in four games, while the Avs went on to beat the Tampa Bay Lightning in the Final. This series was a sobering reminder that the Oilers still had work to do in order to be in the conversation with the league’s best teams.

In the off-season, Duncan Keith announced his retirement and word came out that Mike Smith’s career would come to an end because of injuries. Holland attached multiple draft picks to dump the final two seasons of Zack Kassian’s contract and used the salary cap savings to re-sign Kane and Kulak to four-year contracts while also adding Mattias Janmark in free agency.

The team’s big splash on the open market that summer was signing goaltender Jack Campbell to a five-year, $25 million contract, but there wasn’t an immediate replacement for Keith on the blueline. Campbell struggled mightily in his first season in Edmonton and quickly lost the starting job to rookie Stuart Skinner.

The Oilers were inconsistent during the first half of the 2022-23 season and didn’t hit their stride until Holland finally made the trade deadline swing that fans had been waiting for. He moved Tyson Barrie, top prospect Reid Schaefer, and a first-round pick to the Nashville Predators for defenceman Mattias Ekholm, who was immediately paired in Keith’s old role alongside Evan Bouchard.

The team had a 32-21-8 record when the trade was made and they won 18 of their final 21 games to finish 50-23-9. The Oilers rolled into the playoffs on a nine-game winning streak and took down the Kings in six games in the first round. They again went up against the Pacific Division champions in the second round, this time the 51-22-9 Vegas Golden Knights.

The teams split the first two games of the series in Vegas and did the same with the next two in Edmonton. The Golden Knights took Game 5 at home with a 4-3 win and then came to Edmonton and finished off the series with a 5-2 victory in Game 6. Vegas went on to beat the Dallas Stars and Florida Panthers for their first Stanley Cup, marking the second consecutive year the Oilers lost to the eventual champions.

The Oilers were pressed against the salary cap ceiling in the off-season and Holland opted not to move any major contracts to open up more wiggle room. The team signed players mostly for the Bakersfield Condors, with the most notable addition being former Erie Otters captain Connor Brown. To fit the winger under the cap, Holland signed him to a league-minimum salary with a performance bonus that could be kicked to the following season.

The plan to run it back with an almost identical team to the one that lost to the Golden Knights in the spring looked like a disaster one month into 2023-24. The Oilers started the season with an 8-1 loss to the Vancouver Canucks and had just two wins by the end of October.

A week into November, Jack Campbell was placed on waivers with a .873 save percentage and third-stringer Calvin Pickard was brought up from the AHL. A few days later, the Oilers fired Jay Woodcroft and Dave Manson and brought in Connor McDavid’s former Ontario Hockey League coach Kris Knoblauch and Hall of Fame defenceman Paul Coffey to replace them.

The team rattled off three consecutive wins following the coaching change but they fell back into a three-game losing streak right after. Things clicked during a 5-0 win over the Washington Capitals on American Thanksgiving and Edmonton went on an eight-game winning streak that came one shy of matching a franchise record. After another three-game skid, the Oilers shattered their record with a 16-game winning streak.

The historic run was paused for the All-Star break and the Oilers went up against the defending Stanley Cup champions with an opportunity to match the longest winning streak in league history. A 31-save performance from Adil Hill led the Golden Knights to a 3-1 victory and Edmonton’s streak was snapped at 16 wins.

Edmonton acquired versatile forward Adam Henrique ahead of the trade deadline and added some depth by trading for Sam Carrick and Troy Stecher. The team finished second in the Pacific Division with a 49-27-6 record after rebounding from their 3-9-1 start with a 46-18-5 performance with Knoblauch and Coffey on the bench.

The Oilers breezed past the Kings again in the first round of the playoffs and managed to get through a difficult seven-game series with the Vancouver Canucks in the second round. They took down the Dallas Stars in the Western Conference Final and went up against the Florida Panthers in the Stanley Cup.

After dropping the first three games of the series, the Oilers battled back with two lopsided wins in Edmonton and a gutsy performance in Florida to force a Game 7. They nearly completed what would have been the most incredible comeback in NHL history but the Panthers squeezed out a 2-1 win in front of their home fans to capture their first-ever championship.

Yet again, the Oilers were eliminated by the eventual Stanley Cup winners. This time, they had to watch the other team hoist the trophy.

A few days after Game 7 of the Stanley Cup Final, the Oilers announced that they wouldn’t be extending Holland’s contract and that he would be parting ways with the organization. CEO Jeff Jackson served as the interim general manager during the draft and free agency and former Blackhawks GM Stan Bowman took over the role in August.

The Oilers are heading into the 2024-25 season with the expectation of winning the Stanley Cup. Anything other than that would be a letdown. They’ve come a very long way from five years ago when they entered the 2019-20 season hoping to make the playoffs.

Now that we’ve gone through the meat and potatoes of Holland’s five seasons with the Oilers, Part II of this series will dig into how much credit Holland deserves for the team’s rise.