I was assigned as an advisor to an assistant SecState for a while and I suspect the 2nd email is in reference to these remarks: https://2009-2017.state.gov/secretary/20092013clinton/rm/2011/02/157187.htm
References to the Owl of Minerva come up from time to time in NWO/"Smart Power" circles. "Minerva's Rule" is stated here: http://faculty.arts.ubc.ca/tiberg/Homepage08/Minerva.html And the Progressive Left and NEOCONs eat this stuff up.
Here's a summary: "[T]wo important trends [emerged] in international affairs since the late 1990s. The first trend is an expansion of multilateral institution-building into new arenas. While the post-war period saw the creation of effective global institutions in the field of economic cooperation and development (IMF, World Bank, WTO), security (disarmament treaties), and human rights…. The development of these international institutions includes formal legal treaties, codes of conducts, and norms and practices that shape behavior.
The second trend is a new political pattern in the creation of these institutions. To the surprise of many, as the US decided that institution-building beyond the realms of economy (trade, finance) and hard security (anti-terrorism, non-proliferation) was not in its interest and should be halted, other national and supranational actors joined forces to construct new institutions…. In the cockpit driving the continued trend, one can find what we call “Minervian powers”; in particular, an emergent European Union aiming to project a new common identity, a transforming Japan, and a Canada forcefully dedicated to multilateralism. Under the label of Minervian powers, we refer to a group of advanced industrial democracies with significant economic and military clout, yet also a strong commitment to multilateralism and norm construction. Minerva represents a group of like-minded states that support the creation of credible and binding institutions, possibly backed by a limited but creative use of force."
The reference to the owl goes to an owl taking flight at twilight, after the day is done. The implication is the owl has the benefit of surveying the day after it is done, with all the events and facts in view. C.f. http://www.askphilosophers.org/question/1579
So, this looks to me like Sullivan's referencing inside jargon of the Minervans to imply he thinks the last paragraph might be too heavy with 20/20 hindsight–and being pretentiously wonky in the process.