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I think that Oakley represents the way that Toby had planned for his career; go along to get along and gain enough influence to change the system from within.
Quinn reveals to Toby that "Oakley was the brave chap who led the in-house Foreign Office revolt. Got up the round robin to our Foreign Secretary urging him not to go after Saddam." We know that that didn't work, and there is some implication is that Oakley's career was fore-shortened as a result (although there is also the matter of Hamburg).
I suppose that Oakley wants Toby to carry on and not be a whistle-blower so that he can in a sense carry on Oakley's career; in a sense, he is Oakley's heir.
It was interesting to me that Oakley decided to torpedo his second career (and risk his freedom) by providing additional information to Toby in what must have been a major violation of the Official Secrets Act.
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