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Likely on the cards, however, will be Ukraine and Crimea, long a thorn in U.S.-Russia relations. U.S. government policy refuses to recognize Russia’s annexation of Crimea, deemed illegal under international law. But Trump in recent weeks has left the door open for a reversal, saying only in response to questions on the topic: “We’ll see.”
An about-face on Ukraine’s Crimean peninsula — which was annexed after a 2014 Russian invasion and led to heavy U.S. and European sanctions on Moscow — would completely upend U.S. foreign policy and its stated commitment to ally Ukraine, as well as its historic opposition to Russian territorial expansion.
Trump shocked officials at the Group of Seven (G-7) meeting in June when he argued that the annexed Crimean peninsula should belong to Russia, because “people there speak Russian.” The assertion sharply contradicted longstanding U.S. and transatlantic policy of not recognizing the seizure of sovereign territory by force.
Since 2014, Washington has held sanctions on Russia for its invasion and ongoing war in Ukraine’s east, which has killed well over 10,000 people. The U.S. also provides lethal and non-lethal aid to the Ukrainian military fighting Russian-backed separatists and conducts joint military exercises with the Ukrainians.
White House national security advisor John Bolton failed to quell concerns over the president’s stance, saying in an interview with CBS earlier this month, “The president makes the policy. I don't make the policy. "
“Kiev’s main concern is that President Trump will unilaterally recognize Russia’s annexation of Crimea” — effectively selling it out to the Kremlin, said Daragh McDowell, senior Russia analyst at Verisk Maplecroft. The legality of such a move and whether it would mean a formal recognition of Russian sovereignty over the peninsula is unclear, McDowell said. “However, in practical terms it would further demoralize U.S. allies.”
The meeting comes on the tails of a tense NATO summit during which Trump lambasted allies for not meeting their defense spending commitments. Putin, staunchly opposed to NATO expansion, has sought to take advantage of the growing rift between the Western allies.
While the risks to Russia in taking on a NATO state directly are too high, given the alliance’s Article 5 principle of mutual defense, this would seriously embolden Putin to further push into Ukrainian territory, according to McDowell.
“Russian naval assets in the Black Sea could be used to raid Ukrainian territory or enact a blockade of Mariupol, with the goal of demonstrating that NATO cannot or will not protect other post-Soviet states seeking to reorient their foreign policies towards the West,” he warned.
Trump has insisted that no aid or official from the U.S. delegation be present during the meeting’s initial stages. This has sparked fears that he may not hold to U.S. policy conventions or the guidance of his advisors when matched with Putin, a highly trained former KGB officer.
Crimea may end up as a bargaining chip in a larger foreign policy concern for Trump: Syria.
“The obvious fear in Kiev is of some grand bargain between Trump and Putin, whereby the U.S. cedes Crimea to Russia with sanctions moderation — even though the U.S. has no right in international law to make any such offer — in exchange for Russian withdrawal from Syria or support for U.S. broader strategic objectives in the Middle East,” for instance against Iran, said Timothy Ash, senior emerging markets strategist at Bluebay Asset Management.
“Any such concession could prove greatly destructive to political stability in Ukraine.”
Concessions on Crimea would also violate commitments Washington made in the 1994 Budapest Memorandum of Security Assurances, under which the U.S., U.K. and Russia jointly pledged to respect Ukraine’s territorial integrity.
In the words of Steven Pifer, a former U.S. ambassador to Ukraine under President Bill Clinton, this would “deal a sharp blow to the credibility of U.S. commitments.”
Circuits have crossed on the message Trump will deliver on Monday. American ambassador to Russia Jon Huntsman last week listed a number of issues for which Russia must be held accountable: "Election meddling; malign activities throughout Europe, including the Balkans, U.K. and Brexit, France and Italy, just to mention a few," he told reporters.
Just a day later, Trump told a rally in Montana, “Putin’s fine. He's fine. We're all fine, we're all people.” Trump has long called for improved relations with Moscow, even as Washington tightens sanctions and a federal investigation continues into Russian election meddling and the Trump campaign’s potential ties to the country.
In a joint press conference with Prime Minister Theresa May on Friday as part of his working visit to the U.K., reporters pressed Trump on how he would solve the issue of Crimea, and how he would bring it up with Putin in Helsinki. His response was decidedly vague.
“We're going see what happens, it's a process. If I knew I wouldn’t tell you, that would put us at a disadvantage.”
The president described Crimea as a “bad hand I got handed” from the Obama administration, claiming that the invasion would not have taken place under his presidency.
“I’m not going in with high expectations, but we may come out with some surprising things.”
Christopher Granville, Russia expert and managing director at TS Lombard, doesn’t see any sea-changes ahead for U.S. policy in the area.
“I don’t believe that Trump will actually ‘do’ anything on Ukraine,” he told CNBC. “At most, he may say that it’s a European problem.” Granville added that the most important topic for the president on Monday will likely be Syria, especially as it pertains to the conflict between Israel and Iran.
During his rally in Montana last week, Trump brushed off concerns about the high-stakes summit.
“Trust me, we’ll be fine… Will I be prepared? Totally prepared,” the president said to a cheering crowd. “I’ve been preparing for this stuff my whole life.”