The Druid Wild Shapes into a brand new bear form every time

There is no "bear". There is only "the druid magically assum[ing] the shape of the a bear". HP reduction is not carried over, when the druid Wild Shapes back into their normal form the hp pool that had been reduced doesn't exist, and never will again.

Note: interpreting "health points" to include "maximum health points" is kind of questionable.