The Edmonton Oilers kicked off their five-game road trip with a decisive win over the Maple Leafs on Saturday, and they were looking to keep the good times rolling in their rematch with the Montreal Canadiens. The Habs were rattled by how things went when these teams matched up back in October, and I was fascinated to see how Sunday’s game would shake out. Would it be spicy? Would both teams look tired since they were each on the second half of a back-to-back weekend? Unfortunately, it was the Habs who had all kinds of jump on Sunday, and used those wheels to lock in a lopsided 4-1 victory.

Do you remember when the Oilers had the third overall pick at the 2014 NHL Draft, and everyone was talking about how the Oilers should take Sam Bennett? That was, of course, until he couldn’t do a pull-up. It’s wild to think about now, but there were a lot of people who believed Edmonton should avoid Draisaitl because he was too slow and likely wouldn’t score a ton. More of a passer than a finisher, they said. Well, here we are 11 years later, and Leon Draisaitl has developed into one of the best players on earth. No disrespect to Aaron Ekblad, Sam Reinhart and Sam Bennett, all of those guys are doing very well with the Panthers, but there’s no way that Drai wouldn’t go first overall in that group if we did a re-draft with the benefit of hindsight.

And on Sunday night in Montreal, most of us were waiting for Leon Draisaitl to register his 1000th point and cement himself in history as one of the 100 players in the league to reach the feat. Unfortunately, Drai did not get the point he needed. And the reason I’m writing about this is because I actually thought the rest of the team tried to hard to get him there. There were moments on the power play when clear shots were being passed up to set Draisaitl up with a cross-ice one-timer, when a shot from wherever the puck was would probably have been the better choice. As much as I get why everyone wants to get him to 1000 points, I also think he’s so damned good that it’s going to come naturally without having to force it. Maybe it’s just me, but as someone who bet on Drai to get a point against the Habs, I legitimately thought Oilers were trying too hard to make fetch happen. Big Sexy 2.0 is going to get his point, but I just don’t think everyone around him has to try so hard to make it happen.

Calvin Pickard got his ninth start of the season on Sunday in Montreal, and in the hours leading up to the game, all I could think about was what the last couple of days must have been like for him. There’s a zero percent chance he didn’t know about or hear the noise about the team’s goaltending, and for a lot of people, finding a way to upgrade on Pickard was more critical than upgrading on Skinner. But now that Stan Bowman pulled the trigger to bring Tristan Jarry to town, I can’t help but wonder what the future looks like for our pal Cal. We know the guys in the room love him — they’ve defended him as recently as this season — but the NHL is a results-based business, and Pickard’s haven’t been nearly good enough. But when the team loves the guy and goes to bat for him with the GM, it’s fair to wonder how much the power of friendship comes into play with what happens to Pickard next.

Will Bowman still look to upgrade on the backup position, knowing full well how much our current guy matters to the players in the room? Does he care? Only time will reveal what happens between the crease, but for the time being, we have to hope Pickard can start to round back into form. Against Montreal, I thought Pickard was the best Oiler on the ice. And even though I know I’ll take heat in the comments for giving him love after allowing four goals on 27 shots, it’s hard to ignore that he was faced with multiple breakaways, odd-man rushes, and clean shots from in tight that he mostly handled with care. The guy was on an island for most of the night. Put another way, the Oilers probably would have lost that game regardless of who was in net, and I think it would be deeply unfair to hang this one on Pickard.

It’s not often that we take shots at the Oilers‘ special teams, but I felt like last night’s performance deserved a few words. We all know how dangerous Edmonton’s power play can be, but you wouldn’t have known it from the way they handled their five power play opportunities. While scoring once on five chances with the man advantage isn’t horrible by any stretch, it’s hard not to feel like there were a few more opportunities that could have cashed with a few adjustments. And the first thing that pops to mind was the two-minute 5-on-3 that the boys got in the first period. Even though the Oilers were actually pretty damned good in those two minutes, they ultimately couldn’t score. It doesn’t matter how many looks you get if you can’t get any of them past the goalie. It’s hard not to imagine how different things might have gone had they been able to score there.

On the PK, the Oilers gave up a pair of goals in four shorthanded situations, and it doesn’t take a data scientist to figure out that running a 50% penalty kill is probably going to be a problem. On the first one, Ivan Demidov ripped the puck past Pickard with a perfectly placed shot. Honestly, I’d tend to tip my cap to the shooter on this one, but even if you do respect the finish, the Oilers actually had a chance to clear the puck only moments before. On Nick Suzuki’s goal, Alec Regula lost his position and allowed the Montreal captain to gain the inside ice. Once Suzuki was the first guy to get to the post, the tap-in he scored will likely go down as one of the easiest he’ll ever score at the NHL level. The point being that even if you give the Habs credit for the way they scored their two PP goals, both featured mistakes by Edmonton that should have been avoided. And when you lose the PP and the PK battle in the same game, it’s not hard to understand why the Oilers ended up losing the game.

Take $20 off your first Vivid Seats order of $200+ using promo code OILERSNATION (new customers only, $200 USD minimum before taxes & fees).