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I agree. It may have been top secret that we knew that Anthony Fokker had developed a way to fire a machine gun through the propeller blades of WWI era biplanes, which was a big deal, but...it is laughable to think our knowledge of when and how we knew, and what we planned to do about it would have any bearing on anything today.

So, that is one extreme.

On the other hand, what if we had intelligence in OIF that told us where to find Saddam and his associates that had been delivered by an asset who might still be alive and working today? Obviously, giving that up could be problematic today.

So that is the other extreme.

Where do we stick that pin along the continuum where one side is okay and the other side isn’t?

There wasn't enough information in the article to make any judgments about why his mission was classified then and why it should be classified today. To answer your generic question, you need to review EO13526. There are a number of conditions applied to classifying information. One would be the perceived harm done to the country if the information was known. The second would be the category that the information would fall. See below for the current categories. Having said that, it may be possible that the information about his mission so many years ago under went an automatic declassification review and was deemed unclassified.

From EO 13526

Sec. 1.4. Classification Categories. Information shall not be considered for classification unless its unauthorized disclosure could reasonably be expected to cause identifiable or describable damage to the national security in accordance with section 1.2 of this order, and it pertains to one or more of the following:

(a) military plans, weapons systems, or operations;

(b) foreign government information;

(d) foreign relations or foreign activities of the United States, including confidential sources;

(e) scientific, technological, or economic matters relating to the national security;

(f) United States Government programs for safeguarding nuclear materials or facilities;

(g) vulnerabilities or capabilities of systems, installations, infrastructures, projects, plans, or protection services relating to the national security; or

(h) the development, production, or use of weapons of mass destruction.