T-2. San Antonio Spurs, Detroit Pistons - 5 seasons
The San Antonio Spurs and Detroit Pistons are two franchises that have been working feverishly to establish a core that could have lasting success in the NBA. At this point, it's safe to say that one franchise has had more luck that the other. Interestingly enough, that's probably thanks to the Spurs getting incredibly lucky at the NBA Draft Lottery. Nevertheless, the Spurs are in great hands with Victor Wembanyama leading the way. The Pistons have a solid core as well but they certainly have some bigger questions about their roster heading into the future.
Even though both the Spurs and Pistons are projected to make the playoffs this year, I'd imagine that when San Antonio does finally break this drought, they're going to be a mainstay in the postseason moving forward. I'm not sure we could say the same about the Pistons.
The Spurs aren't under much pressure despite the five-year playoff drought heading into this season. The Pistons, on the other hand, need to show some promise this season. Otherwise, there could be more changes for the franchise on the horizon.