This comment kinda gets to it.... the organization was completely aimless and hopeless before DD showed up. "Strategy" wasn't really in their vocabulary, it was more like throwing **** at the wall and hoping it stuck (such as the Juan Gonzalez trade). And the accumulation of talent that he inherited in 2002 wasn't really anything that could be built off of. The famous "you try and trade 'em" tirade wasn't an act, they literally had little to no means to upgrade their roster coming out of 2002. Even after DD showed up, they still were flawed in a lot of ways... DD was always good at building a team through trades and free agency, but homegrown development never bore much fruit.
We complain a lot, justifiably so, about how Avila ran this organization into the ditch, and he did, but there's a recency bias when people put this current situation on the level of where the team was when Smith was fired / DD took over. Like, the Tigers aren't where we want them to be, there hasn't been enough talent that has accumulated since 2017, it'll probably take a least 2-3 more years to be competitive, but this still is a far more talented roster than the 2003 team ever was in just about every phase of the game.