Tim was good and he deserves respect, but he was the champ in the league that had the 2nd tier heavyweights at the time including. (Yes, Ricco Rodriguez, Frank Mir, Jeff Monson and Andrei Arlovski were the 2nd Tier HWs.) That doesn't mean he was bad at all, but his hypothetical Pride run probably would have looked worse than Chuck's. I don't know if he would have even been able to even string any wins together unless it was over the guys like Heath Herring (maybe) Goodridge, James Thompson, Takayama. And the "Pride guys all juiced" arguement doesn't mean anything, because so did Tim. Tim was so huge he was able to use his hands from a distance that most people never had to deal with and that's where most of his success was. He also had underrated dirty boxing.
I don't think he comes close to beating any of the top Pride guys, they were all more skilled or athletic than the UFC HW's or both. One of the only UFC HWs that had the skill and athleticism was Arlovski, and Arlovski's 2nd fight with Tim kind of is what it is, it was a bit flukey, and the third fight was insanely boring, I believe Arlovksi stated way after the fact that he was injured and that was the cause...
The boring fights are another reason why people shit on Tim. The tail end of his UFC career was extremely lackluster, people couldn't wait for Randy to come in there and take him out. And honestly, the Randy fight was more awesome because of the circumstances than it was a total barnburner.
Having said all of that, he was good for the time in the org that he was in. I think his best win was probably Ricco Rodriguez, who is largely forgotten, but was on a tear up until that point.