Clay Shaw's CIA Connection

As you know, Shaw served as a CIA source from 1948-56. However, there were at least two instances where he stepped out of that limited role and volunteered for something a little extra. Can anyone tell what that was, and what the outcome of the two instances was?

Judson O'Donnell and Clay Shaw

Judson O'Donnell was friends with Clay Shaw during Shaw's New York City days, yet little is known about him. How much do you know?

Clay Shaw Married?

Some have speculated that Clay Shaw may have been married at one time, or at least may have  had a serious relationship with a female. What do you think?