The document explains it. When dealing with these comparators, when chained they get separated and you have the equivalent of this: False == False in [True]

The document explains it. When dealing with these comparators, when chained they get separated and you have the equivalent of this: False == False in [True] => (False == False) and (False in [True]) If you put it into a function like this: def foo(): return False == False in [True] And then disassemble it you'll get this byte code (3.13, may vary by version): RESUME 0 LOAD_CONST 1 (False) LOAD_CONST 1 (False) SWAP 2 COPY 2 COMPARE_OP 72 (==) COPY 1 TO_BOOL POP_JUMP_IF_FALSE 5 (to L1) POP_TOP LOAD_CONST 2 ((True,)) CONTAINS_OP 0 RETURN_VALUE L1: SWAP 2 POP_TOP RETURN_VALUE There is no literal `and` operation occurring here, instead it first does the `False == False`, then jumps if false or continues to the second comparison. For the literals we've given it, it'll go on to the second comparison which will result in false since `False` is not in `(True,)`. EDIT: And here's the non-chained version disassembled: def bar(): return (False == False) in [True] RESUME 0 LOAD_CONST 1 (False) LOAD_CONST 1 (False) COMPARE_OP 72 (==) LOAD_CONST 2 ((False,)) CONTAINS_OP 0 RETURN_VALUE