Then billion-dollar real estate developer Steve Witkoff’s meeting with Russian President Vladamir Putin went a little something like this… Mr. Witkoff has other plans. He’s been a long-time confidant and advisor to former President Donald Trump. This meeting would be their fourth wrap in a little over two months. This heavy-handed new approach to diplomacy has been met with skepticism—even concern—in both Kyiv and Europe.
Witkoff isn’t your average diplomat, he’s developed an unusual relationship with Putin. According to leaked reports, he’s spent more in-person time with the Russian autocrat than any other American. His prior meetings have spurred criticism over the lack of Ukrainian participation in these dialogues. This episode reveals the tenuous balance of U.S.-Russian relations, especially in light of the recent conflicts in Eastern Europe.
On his most recent trip, Witkoff travelled to Moscow with a translator on board. He attended a meeting at a table in the Kremlin, where he was flanked by key Russian officials, including veteran foreign policy aide Yuri Ushakov and Kirill Dmitriev, Russia’s envoy on foreign investment.
In July 2018, Witkoff described his high-level negotiations with Putin as “constructive and very useful.” This indicates that these discussions had the potential to result in beneficial changes. His cavalier style of diplomacy is fully dependent on personal relationships. This approach reflects the deal-making style that characterized Trump’s presidency.
“It’s so good to see you,” – Steve Witkoff
What these meetings have shown is the extent to which high-level diplomacy has fundamentally changed during the Trump era, and not for the better. Rather than career diplomats, dangerous, influential men like Witkoff are filling critical positions. This style of engagement raises critical questions about the direction of American foreign policy. More importantly, it fuels worries that formal diplomatic channels could be further marginalized.
Others view Witkoff’s courting of Putin as a more savvy approach to start the discussion. As these new deals are being signed, others lament the effects that this business may have. As one European diplomat told us, observers in Kyiv and throughout Europe are extremely worried. They fear these talks could decrease Ukraine’s negotiating power and further complicate the already fraught geopolitical environment.
Witkoff’s background in real estate and deal-making has drawn parallels to Trump’s own career, highlighting a blend of business acumen and political maneuvering that shapes their interactions on the global stage. As the U.S. navigates its relationship with Russia amid ongoing conflicts, Witkoff’s role as an informal emissary raises important questions about the future of U.S.-Russian diplomacy.
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