I remember having so much optimism in 2002-03. Halladay broke out. A position player core all coming up at the same time in Wells, Phelps, Hudson, Hinske (ROY season), Werth, etc. Made some interesting trades for Prokopec, Jason Arnold, JF Griffin, etc. All of them busted, but looked decent at the time. Escobar was wasted as a RP but was finally moved to the rotation for good in 2003 and looked to be turning into a long term piece, though they ended up not re-signing him and he turned into a really good SP for a few years with the Angels. Not finding a way to bring him and Carpenter back really hurt long term, obviously Carpenter more so. More than anything, the Jays hired someone from Beane's front office before Moneyball was a thing. I thought we were going to be the Toronto A's, which would have been a huge compliment around that time.
Regardless, in hindsight, 2002-08 wasn't that bad. Had some fun years and there wasn't the level of ineptitude like there was during Ash's years. Still wasn't a good period in Jays history, but from 94-14, we had to take what we could get.