I have found interesting email threads related to exactly same issue. But it looks like it was fixed since then, not sure why it reproduces for me again:

http://lists.gnu.org/archive/html/emacs-orgmode/2010-12/msg00443.html
http://article.gmane.org/gmane.emacs.orgmode/34802

Dima

On May 15, 2014, at 2:49 AM, Dmitry Gorbik <dgorbik@me.com> wrote:

It reproduces in console for me as well. 

Here is a screenshot to demonstrate the frame size and the issue:
<Screen Shot 2014-05-15 at 2.18.52 AM.png>

Thanks,
Dima

On May 15, 2014, at 2:44 AM, Bastien <bzg@gnu.org> wrote:

Dmitry Gorbik <dgorbik@me.com> writes:

This is my org-mode version:

Thanks -- maybe try to define "large enough" from your previous
report, so that other emacsformacosx users have more infos on how
to reproduce the bug.

--
Bastien