Building off this thought, I used B-Ref to see the standings on December 30 in each of those years (a few years of lockout means a few years' data were missing).
There was only one year that was close to the situation this season (with five teams under .250); that was 1997, with 4 teams under .250 at this point of the season along with two other teams that were at .250 exactly. That season led into the 1998 draft (Danny Manning, Rik Smits, Charles Smith, Chris Morris, Mitch Richmond, ...).
Two other years also had as many as 4 teams under .250: 2012 (Anthony Bennett, Victor Oladipo, Otto Porter, Cody Zeller, Alex Len, ...) and 2023 (Risacher, Sarr, Sheppard, Castle, Holland, ...).
Frankly, I'm surprised to see that these drafts were the seasons that had so many teams toward the bottom. Maybe it means that there's not really much connection between draft quality and the commitment of teams to losing.
During Wemby's upcoming draft season, only one team was below a .250 winning percentage on December 30, and Spurs themselves were at .343.
The previous year (with Chet, Paolo), there were two teams below .250. Thunder were at .353.