An alternate history scenario for the Oilers:
How to make this team better. I'm only focusing on the Ken Holland era, which started in 2019. And I'm completely ignoring the drafts here. One can make too many GMs look like fools by examining their draft history. I'm not going to play that game.
First thing Holland should've done differently is in 2020, resign Athanasiou. He had just paid two second round picks for him. I get this move hadn't worked out, but paying two good picks just to let a guy leave a few months later is awful. AA is a speedy player. He could've been paired with McDavid for at least the 2021 season. That season lasted 56 games, surely AA would've scored 20 goals and 35 points while playing with McDavid, right?
Then, on to the 2021 offseason. First, Holland should've NEVER, and I mean, NEVER let Larsson walk. The contract he signed with Seattle was a 4 year, 4M AAV one. If he had to, Holland shoul've overpaid to keep him. Like, 5X5. Sure, that would've been a bit too much, but losing Kelfbom in 2020 and a year later, losing Larsson, was just not something realistic. Cause, without Larsson, the Oilers turned to Cody Ceci and Duncan Keith to replace him defensively. Keith had regressed a lot by 2021 and Ceci is no Larsson. And we've seen what Larsson has done with Seattle, he's quietly been a steady presence of their top pairing.
Then, in 2021, entering Holland's third season, the Oilers badly needed an upgrade in net, and the tragic thing is, there were quite a few guys who could help with that on the market that year. Fleury could've been a one year stopgap, Linus Ullmark would've been great too or even F. Andersen. Smith was too old for a big workload and Koskinen was overpaid for what he brought. I would've personally called BUF and offered to retain 1M on Koskinen's deal and trade him there for like a 6th round pick in 2022. BUF played a 40 year old Craig Anderson and Dustin Tokarski that year. Koskinen was better than Tokarski at least. In fact, MK wasn't a bad goalie. He was in fact a decent 1B guy, but overpaid by 1,5M. Thx Chiarelli for that.
Let's say EDM sign Andersen. 2 year, 5M per. No need to sign Campbell, then.
Now, to recap a few of the changes I would've made to this team, by that point in time, I wouldn't have Ceci or Keith or Koskinen in the lineup, but I'd have AA, Larsson and Andersen, meaning, a good middle six forward, a steady shutdown top pairing RD and a good starting goalie.
I wouldn't have signed Hyman. There, I said it. I get why Holland got him. He needed a winger for McDavid for the foreseeable future. That was understandable. What wasn't, however, was doing so while forgetting the goaltending and not upgrading the defense, which, btw, I would've done by adding UFA Jake McCabe. This would've left the Oilers with a bit of money to spend up front, and, while not being able to get Hyman, others could've and would've been fits. Tatar, Rodrigues, Saad, P. Suter, Haula, F. Gaudreau and Johansson would've all been players that would've added some much needed depth to this roster. Say, the Oilers sign F. Gaudreau and Haula. You add that to AA, Puljujarvi, Yamamoto and Foegele and you would've had decent wingers to surround McDavid, Draisaitl and RNH down the middle.
Your defense could've looked like this:
Nurse-Larsson(much better than Nurse-Ceci)
McCabe-Barrie
good shutdown defender-Bouchard
C. Jones
Offense:
Haula-McDavid-AA
F. Gaudreau-Draisaitl-Yamamoto
Foegele-RNH-Puljujarvi
At the 2022 deadline, thx to Bouchard's emergence as the PP quarterback, you could've even traded Barrie along with other pieces for a better defensman when it comes to defense. Could've possibly even tried getting Severson from NJ! Could've even tried adding some depth to that offense at the deadline. Domi?
That would've been a better plan than to go all in on offense, which doesn't work.
By now, you wouldn't have the horrendous Campbell deal, you would've had more flexibility without Kulak and his almost 3M per deal (no need for him in my scenario) and Hyman and his deal that'll age bad. I'd even argue Nurse's cap hit would be lower because with McCabe and Larsson he would've had less playing time. Maybe 8,5M and not 9,25M? 8M even?
In other words, the Oilers would be in a much better situation right now. In 22-23, you could've had Andersen mentor Skinner and I know Andersen has some health issues right now but by now the Oilers could've probably figured out their goaltending.
TLDR: in 2021, Holland should've forgotten about Keith and Hyman and instead focused all his time on bringing back Larsson and signing a true starting goalie.