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
>> 
>