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The WSJ describes that during the first meeting between Witkoff and Putin, the US representative continuously took notes while listening to the Kremlin leader lecture about Russia's "thousand-year history." At the same time, Putin was assessing whether the man sitting across from him was genuinely open to the Russian position.
The newspaper also highlights that Witkoff has already made six trips to Moscow, while never visiting Ukraine. According to a White House representative, Witkoff flies to Russia on his private jet and pays all expenses himself.