According to Allen Poteshman, assistant professor of finance at the University of Illinois at Urbana-Champaign, there might be some truth to max pain theory. I'm not going to even try to explain max pain theory. But I will try to summarize his interest in equity options and their trading leading up to expiration.
Poteshman says that options writers (sellers) will buy and sell the underlying so that the options will expire out of the money. This makes sense because it can cost the writers of options less to try to manipulate the stock price than they would pay to options holders. Of course this would not work for highly liquid stocks like an Intel or an IBM, but it would work for less liquid issues. Max pain theory tries to take all of the mixed incentives of all of the options writers and determine at what price they collectively would like to have the stock close at expiration to minimize their costs or extract the "max pain" from options holders.
The article (PDF File), co-authored with Sophie Xioyan Ni and Neil Pearson and will be published in the Journal of Financial Economics.
(Note: This is the first post I'm doing from the new Hyde Park Center! The building is great, although I think that everyone is still getting used to it. It is very difficult to orient yourself downstairs, but still it should be a great new home for the GSB.)