I'm not a hardcore Treliving defender or anything, and I've been underwhelmed with this off-season, but I think it's not completely fair to judge these without understanding the situation he was in and essentially having to make these trades under duress with pressure from a meddling owner who wanted the team to remain competitive in the short-term to continue selling tickets and getting post-season revenues, and forcing his hand with things like coaching selections even (e.g. Sutter). It's clear that relationship was broken by the end as it was reported that Treliving had received offers to stick around in Calgary, but he himself chose to leave.
With Tkachuk, it was reported that Treliving was originally seeking a futures package and had some good offers, but ownership wanted established NHLers so he pivoted to Florida's offer. On paper it looked like a good trade and many even thought Calgary got better by adding Weegar and Huberdeau. Weegar has played well for them, Huberdeau has obviously been a major disappointment although he showed some signs of life in the second half of this past season. But coming off a 115 pt season at the time, can you tell me with a straight face that you thought Huberdeau would immediately crater after to the point he has? Kadri also just had an excellent season where he played with rookies on his line.
He's made good trades before, such as the two Dougie Hamilton trades.