The funny thing is EDM could have had Bishop had they not haggled over which 2nd round pick would be included in the trade. 20 spots in the draft cost them a shot at Bishop. Even worse, they never even used that pick. They traded down in the draft multiple times in a series of swaps that eventually culminated with them walking out of that draft with a paper clip. What would you prefer to have, Ben Bishop or a paper clip?
With that said, who knows how poorly Bishop might have further developed in Edmonton. Being developed in Edmonton almost cost Dubnyk his career. Since getting an opportunity on a team that isn't a tire fire, Dubnyk has proven to be a serviceable NHL starting goalie.
It is hard to hold the trade against Ottawa because I don't think a lot of teams anticipated Bishop becoming a Vezina contender. St.Louis ditched him for a second, Ottawa was ready to ditch him for the 36th pick to EDM, and EDM wasn't willing to part with an early 2nd for him, they wanted Ottawa to accept Anaheim's 2nd instead which was projected to be in the final 10 picks of the round. Had any of those three teams anticipated that Bishop would have reached the heights he has, they probably would have held on to him, or at least asked for more in return.
When it comes to Tampa, I don't know where they stood on Bishop, and where they stood on Conacher, and if they specifically were moving Conacher because they were sly and selling high on him, or if they thought they had something in Conacher but were being aggressive to get a young starting goalie. Remember, before going after Bishop Yzerman gave up a very big haul for Lindback. It consisted of the 37th, 50th, and 63rd picks over two drafts. Obviously, Lindback didn't work out, but what I am trying to illustrate is that he had been aggressive in the past when it came to giving up high value packages to try and solve his goaltending situation. If it is true that Bishop would have been an Oiler had they been willing to give up the higher of their two 2nd round picks (36th overall), that would point to Yzerman being unwilling to beat that trade offer. Which might mean that Yzerman wasn't the smartest guy in the room who swindled the Senators, he just lucked into getting a good deal on a player who exceeded expectations.
The Conacher for Bishop trade will take on mythical status as perhaps one of the worst trades the Senators have ever made. Should the regime be blamed for making the move? Maybe not. Just because the move is terrible in hindsight doesn't mean that it wasn't the right move at the time. Hindsight is the best GM but unfortunately, he isn't a real person so no one can hire him to run their team.
When you consider it as one of the worst Senators trade of all time, you have to consider that at worst the Senators gift wrapped the Lightning a cornerstone goalie in exchange for a hobbit on skates who was banished to play hockey in New Zealand or something after not being able to cut it on the AHL Sabres. While at best, Conacher's contributions helped Ottawa get enough points to not only make the playoffs but do it in the 7th seed where they matched up against Montreal which spawned the most memorable hockey line of all time...."no respeck".....in 30 years it'll be remembered up there with Bobby Orr's flying goal......just you watch.