President Barack Obama is an inspiring orator and a gifted storyteller.  So why did his speech at Moscow’s New Economic School go over so poorly (other than the genuine laughter at his gratitude for Alexander Ovechkin playing for the Capitals)?

There is a set formula these days for presidential addresses designed “for the Russian people”—going back to Ronald Reagan’s famed May 1988 address at Moscow State University.  Praise for Russian culture, some reference to past U.S.-Russia cooperation, the paeans to American freedom and veiled criticisms of the Russian present, ending with the call for renewed cooperation between the “two great nations.”  By these standards, president Obama gave a good speech.

But I believe he missed out on a real opportunity to have a “heart-to-heart,” particularly with the demographic that matters most to the U.S.—the young and well-educated, who will be staffing the key positions in the economy and government in the future.

Obama, after all, comes to the presidency not as a tabula rasa, but as a U.S. Senator whose votes have shaped U.S. policy toward Russia and Eurasia.  As governors, Bill Clinton and George W. Bush may have had ideas about U.S. foreign policy, but as a senator, Barack Obama (along with Hillary Clinton and Joe Biden) was impacting it.

We know that many Russians, not just the government elite, are concerned about the expansion of NATO.  This is an emotional red-line issue.  When in the Senate, Obama cast votes that commit the United States to pursue NATO membership for Georgia and Ukraine.

What might have been the impact of a speech, then, where the president said something along these lines: I know NATO expansion is a sensitive issue for you.  Let me explain why I support it, why I think it is in America’s interests.

Perhaps the president could have cited some of the intellectual support for the position he endorsed.  One of the senior statesman of the Democratic party, Zbigniew Brzezinski, laid out the argument that NATO expansion eastward eliminates “any geopolitical ambiguities or temptations in the areas immediately west of Russia” that could lead to conflicts or instability that could in turn affect U.S. interests in Europe.  Was that an influence on his thinking?  Did the president endorse the argument, put forward by many, that closer security ties between countries like Georgia and the United States might have prevented the 2008 war—because when the U.S. has real, binding obligations to enforce, it works to moderate the behavior of its allies—citing the example of Taiwan and how Washington tapped down the calls for independence so as to avoid a major rupture with China?

Or perhaps Obama thinks geopolitically—and sees NATO expansion to Ukraine, Georgia and perhaps even Azerbaijan as a way of guaranteeing the security of the Black Sea basin and its sea-lines of communication?  Perhaps during his time in the Senate he met with the Romanian ambassador to the United States, Sorin Ducaru, a forceful proponent of the view that “the Black Sea has been an important geographic location both strategically and economically?”

What about U.S. domestic politics?  Obama, after all, was the senator from Illinois, and Chicago is home to some of the largest eastern European diasporas in the world—many of whom retain suspicions about Russia’s long-term intentions and who want to see the “old countries” protected.

President Obama could have told this Russian audience his intellectual and political journey to support NATO expansion.  He could have said to them, while I don’t expect you to support it, at least you should understand why I and others in Washington favor the expansion of the alliance to include Ukraine and Georgia.

But none of this appeared.  Instead, the president, in his speech, made it seem that the only thing that guides the U.S. desire to see Georgia and Ukraine in NATO is respecting the abstract principle of sovereignty and how this will make the world a better place.  It is just supporting our values.

One doesn’t have to be a throwback to the 19th century to say that argument is unconvincing!  Surely there must be some vital interests at stake—either directly affecting America or her allies.  The whole point of the “reset” was to be able to speak frankly and honestly with Russia.  So why did the president not take this chance?

Nikolas K. Gvosdev, an Atlantic Council contributing editor, is on the faculty of the U.S. Naval War College.  The views expressed are his own and do not reflect those of the Navy or the U.S. government.