Associativity of “in” in Python?

1 in [] in 'a' is evaluated as (1 in []) and ([] in 'a').¹

Since the first condition (1 in []) is False, the whole condition is evaluated as False; ([] in 'a') is never actually evaluated, so no error is raised.

We can see how Python executes each statement using the dis module:

>>> from dis import dis
>>> dis("1 in [] in 'a'")
  1           0 LOAD_CONST               0 (1)
              2 BUILD_LIST               0
              4 DUP_TOP
              6 ROT_THREE
              8 CONTAINS_OP              0        # `in` is the contains operator
             10 JUMP_IF_FALSE_OR_POP    18        # skip to 18 if the first 
                                                  # comparison is false
             12 LOAD_CONST               1 ('a')  # 12-16 are never executed
             14 CONTAINS_OP              0        # so no error here (14)
             16 RETURN_VALUE
        >>   18 ROT_TWO
             20 POP_TOP
             22 RETURN_VALUE
>>> dis("(1 in []) in 'a'")
  1           0 LOAD_CONST               0 (1)
              2 LOAD_CONST               1 (())
              4 CONTAINS_OP              0        # perform 1 in []
              6 LOAD_CONST               2 ('a')  # now load 'a'
              8 CONTAINS_OP              0        # check if result of (1 in []) is in 'a'
                                                  # throws Error because (False in 'a')
                                                  # is a TypeError
             10 RETURN_VALUE
>>> dis("1 in ([] in 'a')")
  1           0 LOAD_CONST               0 (1)
              2 BUILD_LIST               0
              4 LOAD_CONST               1 ('a')
              6 CONTAINS_OP              0        # perform ([] in 'a'), which is 
                                                  # incorrect, so it throws a TypeError
              8 CONTAINS_OP              0        # if no Error then this would 
                                                  # check if 1 is in the result of ([] in 'a')
             10 RETURN_VALUE

1. Except that [] is only evaluated once. This doesn’t matter in this example but if you (for example) replaced [] with a function that returned a list, that function would only be called once (at most). The documentation explains also this.