Trump's "job is to bridge" the parties in the conflict, Fleitz told ABC News, and test whether Putin is sincere about wanting an end to the war. Fleitz said he thinks Trump will have a "very critical eye" toward Putin and be "very quick to implement sanctions" if he judges Putin to be playing him.

Hundreds of protesters gathered in Anchorage to protest President Donald Trump's high-stakes meeting with Russian President Vladimir Putin.

Follow live updates as Trump and Putin convene in Alaska to discuss what's next in the Ukraine war. Trump has pushed the countries toward a peace deal in recent months.