I've skimmed through this thread and may have missed it, but has
@Zow posted the rosters of both teams before the trade?
To me that's a pretty relevant piece on how the trade is analyzed.
My main takeaway was that a newb team traded three players that ate up (something like) 70% of his startup auction budget for three players that ate up (something like) 40% of the commish's startup budget.
Regardless of how the draft played out and what bargains were unearthed at positions of strength, that shouldn't happen one week removed from the draft where nothing substantial happened to the main pieces involved. Self destructive trade made by a player that's clearly new to fantasy.
This is accurately described. Also, the trade occurred less than 48 hrs. after the auction (of a brand new league where some of us know each other but only the commissioner knew the newb), so the players truly had quantifiable values making the newb's offer entirely nonsensical. The nonsense was compounded by the fact that the newb's explanation was that he wanted players from the same team because, astoundingly, that meant he got double points.

So, respectfully, the roster makeups don't seem entirely relevant here. As to their makeup though, and this is probably what bothered me so much, the commissioner's roster was weak at QB and WR and the trade gave him two cornerstones at those positions essentially vaulting him to the clear best and most rounded roster (which really shouldn't occur after what seemed like a "good" auction). Given that the commissioner is a very good commissioner and owner, this appeared to give him an immediate disproportionate boost to his team so quickly. As a result, several of us other owners immediately felt disadvantaged even though the trade wasn't outside the rules and felt compelled to speak up.