Sam Jaffe has some attraction .... he was actually caught working for the KGB, and CBS (reluctantly) had to let him go.
What was the name of that annoying New Zealand Red who was running all over South Vietnam, dirking our guys in the back? He'd be another one.
C.P. Snow is probably too old, too long ago (he was part of the "who lost China" crowd).
Among the current players, Christiane Ahmanpour comes to mind, with her foreign-service husband and globetrotting POV.
Andrea Mitchell's another, sleeps with the Establishment gargoyle Alan Greenspan, and is a redoubtable table-pounder and story-tilter on behalf of liberaldom.
I think monthly would be too often .... you'd run out of really notorious people like the infamous "pseudo-conservative" WaPo blogger Dave Weigel (neocon Palin-hater Jennifer Rubin has his job now and is making a name for herself; she's one of those people who are passionately on your side .... 53% of the time), e.g., or Jonathan Alter.
Peter Arnett should be considered.
Time the award with the Pulitzer. For that matter all to often the award will go to the same person. When was the last time a Pulitzer was awarded to someone who did not advance the far left’s agenda?