Most of this seems to be coming from Wheeler's failing draft grade. But keep in mind Wheeler is a bit sheepish about Ottawa in a lot of ways, mostly because he's been made to look pretty bad based on the prospects he gambled on dropping in his rankings over the last few years. He probably cringes every time he watches Sens highlights and curses Trent Mann.
In 2018, Wheeler went off the board and ranked Brady Tkackuk #9. Beside the Athletic (Cory Pronman did the same), no one else had him below #4 in the rankings out there. Accordingly, he was critical of our pick after the draft. So whether he chooses to admit it or not, at least unconsciously he had a vested interested in seeing Tkachuk not have success as a means to validate one of his only interesting takes from his personal 2018 ranking. When you're alone with a ranking like this, it makes it clear this is squarely on your own personal judgement, so the stakes are high when this is basically your profession to write about this stuff as an expert. Obviously his take does not look good at this point, so every time he sees Brady in the Sens uniform doing something well, he likely throws up in his mouth a little bit.
Then last year, Wheeler once again decided to go with an outlier in the top 10, putting Stutzle at #7. This one was perhaps even more out there, because only one other ranking had Stutzle outside the top 3, and that was at #4. And almost everyone believed there was a consensus top 3, with many having Jimmy at #2. But Wheeler placed Rossi, Raymond, Holtz and Drysdale ahead of Stutzle as his "interesting / original" ranking of 2020, that was clearly a personal take once again.
Fast forward to last season, with Stutzle and Tkachuk thriving and looking like arguably the best guys from each of their respective draft classes, Wheeler has to be hoping everyone just forgets about those two rankings. And when the Sens draft someone, I can't help but wonder whether he hopes are scout can eat some humble pie at some point. He's been losing badly second guessing the Sens so far, but likely sees himself all in, so not surprised. At the same time, Boucher WAS off the board, so there is no major shame putting a "failing grade" basically in line with deviation from the public consensus. I'd probably call it something else other than "failing" given the arrogance of that statement when the kids haven't played it out yet, but he's trying to be interesting and help sell subscriptions, so not a major issue.
As a side note, in 2019 Wheeler's big outlier was Seider at #35. Again, probably the worst possible guy to put your own reputation on the line, when he ends up being a top 10 pick (even though consensus was around #20) and looks like he should have been drafted even higher.
Tough run for Wheeler, basically. Feel for the guy, and as such, don't see much reason to be upset about our scouts going off the board a bit.