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For what it's worth: I figured out how this happened. Maybe it's obvious to you, but this behavior baffled me until I went back and looked at the revision history.
In revision e260d6daf784, the argument parsing for itertools.repeat looks like this:
 Py_ssize_t cnt = -1;
 if (type == &repeat_type && !_PyArg_NoKeywords("repeat()", kwds))
 return NULL;
 if (!PyArg_ParseTuple(args, "O|n:repeat", &element, &cnt))
 return NULL;
 if (PyTuple_Size(args) == 2 && cnt < 0)
 cnt = 0;
In the subsequent revision, 3dbdbc5e6d85, it was changed to this:
 Py_ssize_t cnt = -1;
 if (!PyArg_ParseTupleAndKeywords(args, kwds, "O|n:repeat", kwargs,
 &element, &cnt))
 return NULL;
 if (PyTuple_Size(args) == 2 && cnt < 0)
 cnt = 0;
The original intent is now clear: only allow "cnt" to be -1 if it wasn't specified as an argument. The author simply forgot that "times" could now be passed in as a keyword argument too.
What the author *probably* wanted was something like this:
 PyObject *times_keyword;
 ...
 times_keyword = PyDict_GetItemString(kwargs, "times");
 Py_XDECREF(times_keyword);
 if ((PyTuple_Size(args) == 2 || times_keyword) && cnt < 0)
 cnt = 0;
But I suggest it's far too late to change it to that now.