Thibault was the hottest goaltendng prospect at the time so it wasn't as awful as some might make it seem. I was far more shocked at giving up Leclair and Desjardins for Recchi and trading McDonagh and Higgins for Gomez who actually should have had negative value at the time.
Don't get me wrong, I did not like the Roy trade but the other two I mentioned were absolutely asinine.
The Roy trade was the worst both in hindsight and at the time of the trades.
The one you're completely off is the Gomez trade. McDonagh had a bad season that year, I remember some people complaining of Timmins that season and saying it was another wasted first round pick. And Gomez's value wasn't what you said. Aside from the 08-09 season, his production was on-par to what he had done before and his value was high, as out of all the NHL players at the time, Gomez's ppg in the playoffs was top 5 in the whole league, as he had 50 points in his last 50 playoff games prior to getting traded. The Gomez trade value was bad in hindsight only, and at the time it was actually hated because he was a small forward when people were wishing for a big centerman and some still believed in McD, rightly so, still, McD's value wasn't Subban's value. We could've gotten a lot more if we traded Subban at the time. That's another thing people forget. We had Subban that year who played tremendously in the WJC, and whose value was probably amongst the highest of all blue chip prospects at the time, which was far from being the case with McD.
For Desjardins-Leclair, people say Desjardins was average before getting traded, which I disagree. Yes Reechi had the most value out of that trade, still losing our #1D was what opened the door to Roy leaving. Desjardins was already a #1D back then and that hurt us more than anything. Leclair becoming what he did just added insult to injury, and most people talk about Leclair when they mention that trade, but at the time I was most perplexed about losing Desjardins, especially with how good he was in the 93 playoffs. People say Roy this and Roy that when they talk of the last cup, but there wouldn't be a cup if Desjardins wasn't there.
The Roy trade was the worst because there wasn't a bonafide star player coming back. No matter Thibault's potential, he hadn't shown anything that permitted anyone to believe he would become at least a top 10 goalie in the league.