My take:
Holloway was expendable, given the 'win now' Oilers' mentality. I would have preferred to keep him as I like the player, but his skill-set is already well established on the roster by several other players (albeit older players).
Broberg was mis-played by Ken Holland and Woodcroft / Knoblach. I think Broberg would have gotten his regular job with Edmonton... if they hadn't acquired Ekholm. Once Ekholm arrived, it sent Bouchard to the moon and relegated Brobeg to the minors, perpetually. Then, he started griping about it. My pet theory here is that Kenny Holland -- veteran GM / pal of Yzerman, Lidstrom, McDavid, etc. -- was never going to want to appear to be appeasing young Dmen who are unproven. So, he let Broberg wait. Meanwhile, Ekholm, Nurse's contract, and Kulak meant that Broberg wasn't going to get a chance in the short-term. That was sort-of understandable (maybe), but then it was really on Holland to deal him faster. They could have gotten a decent return, say, late last season or something. (Or in early summer if the Oilers had actually had a GM.)
But I don't get the Ryan McLeod thing at all. Sure, glad to have a prospect in Savoie, but if the club is in 'win-now' mentality, why trade a 25-year-old homegrown player who checks several boxes the Oilers need (youth, speed, PK, size) for a tiny-sized junior player who's not going to impact the McDavid era (much)? McLeod could be frustrating in his aversion to ever going to the net and his lack of physical play, but he is a player the Oilers spent years developing through the system, and successfully.
I have some sympathy for Bowman Jr. in that he was only on the job for 15 minutes when the St. Louis offer-sheet came around. He blew it, but it was a thing that Holland should have dealt with earlier.
I think the Oilers' brass need to be more hard-ass and less in thrall to the (a) the team's superstars and (b) the media. For example, when Bowman Jr. came aboard, I'm sure all the talk by the Oilers' brass to him was, "the priority is to sign Draisaitl"... because the media kept asking about it. And they want to please Connor and Leon. Which is fine, but where was Draisaitl going? He wasn't going anywhere, and he could have waited another week while they dealt with some slighly lesser players who are nevertheless very important.
I sometimes feel like the Oilers' org operates under the rule: "If the media is pacified for now, then we've done our job."