OK, changed my mind once more on this.  The comparison hierarchy is
now

    None < all numeric types < all other types

so that once again

    map(max, Squares(3), Squares(2))

equals

    [0, 1, 4]
diff --git a/Lib/test/test_b1.py b/Lib/test/test_b1.py
index 97462b1..ea09d0b 100644
--- a/Lib/test/test_b1.py
+++ b/Lib/test/test_b1.py
@@ -483,7 +483,7 @@
     raise TestFailed, 'map(int, Squares(10))'
 if map(None, Squares(3), Squares(2)) != [(0,0), (1,1), (4,None)]:
     raise TestFailed, 'map(None, Squares(3), Squares(2))'
-if map(max, Squares(3), Squares(2)) != [0, 1, None]:
+if map(max, Squares(3), Squares(2)) != [0, 1, 4]:
     raise TestFailed, 'map(max, Squares(3), Squares(2))'
 
 print 'max'