Was Trump’s Russia-Ukraine summit doomed from the beginning?

U.S. President Donald Trump engaged in back-to-back summit-level negotiations about the future of Ukraine in Alaska and Washington. The result seemed far from what Trump had hoped for – it was clearly not the “art of the deal” that he has prided himself on.

And yet peculiarly, there is a growing sense that serious ceasefire negotiations may finally begin.

The two summits were by no means the art of diplomacy, but rather a doomed deal-making. Since joining the Japanese foreign service in 1978, I have witnessed, engaged in and followed various diplomatic negotiations for nearly 50 years. Negotiations are difficult to conduct as you desire, because there are always other unpleasant parties involved. I have never thought of myself as a “master negotiator,” but I have found that there are only three types of diplomatic negotiations.

The first kind are negotiations that are doomed to “fail” from the beginning, and the second are the ones lucky enough to be “successful.” The third category is the vast majority of the rest. While successful negotiations do occasionally happen, they account, in my view, for less than 10% of all talks. The third category includes negotiations that either fail to reach an agreement, end in a “draw” at best, or, if luck is against them, collapse at the final stage.

Unfortunately, the recent U.S.-Russia summit falls squarely into the first category.

Negotiations are doomed to fail, if you neglect both reality and standard practices that must never be ignored.

First and foremost, negotiations are dictated by a thing called reality. Some of it may be alterable, though most of them are not. Negotiations that attempt to change such unchangeable reality are often doomed to fail. Diplomatic negotiations are, by definition, a battle of words, not that of physical or military power.

The reality surrounding the Ukraine ceasefire is extremely harsh. Russia has already either annexed or occupied one-fifth of Ukraine's territory. Its desire not to return the territories has remained unchanged since the Russian Empire. Furthermore, Russia refuses to recognize Ukraine's NATO membership and demands that it becomes a neutral entity harmless to Russia. Finally, Moscow hopes that the West respects Russia as a “great power.” This reality remains as long as Vladimir Putin remains in power.

In diplomatic negotiations, “standard practices” matter. They are shortcuts to success that have been developed over decades by professional negotiators.

They are: firstly define national interests, prepare multiple means to achieve them, establish a negotiation strategy, seek allies, devise tactics to isolate your opponents, engage in talks, starting at the working level and then elevating it to the ministerial level; narrow down the issues to be agreed upon and then finally to reach an agreement at the top level.

This is the “standard practice” in professional diplomacy, and I have never seen a successful negotiation that ignores it.

So how did things play out in Trump’s talks with Putin and Volodymyr Zelenskyy? Trump’s standard procedure is to attempt to negotiate with Russia in a top-down manner. There is no evidence that negotiations began at the bureaucratic level, nor is there any indication that professional experts from the State Department or the National Security Council engaged in detailed discussions with their Russian counterparts. At the summit in Alaska, only the date and location were decided in advance, but the agenda remained unclear until the very end. Under such circumstances, it is unlikely that negotiations will proceed smoothly. The world is not that forgiving, unfortunately.

So what’s the outlook? Let’s start off with assessing the hard cold realities.

First and obviously, Putin is untrustworthy. He does not tell the truth, but his war aims are clear. It is truly unacceptable to the West, but he does not lie much about his bottom line for the conditions of a ceasefire – that he wants the annexed territories, and NATO out of the picture.

The second reality is that Trump is also untrustworthy. But in contrast to Putin, Trump’s lies are conditional. He does not hesitate to lie for his own benefit, not for the sake of the nation. Moreover, he is easily swayed by what he was told just before he speaks, making him extremely difficult to deal with. In that sense, Trump is an inconsistent liar.

Third, European NATO countries move at a glacial pace. Despite it being summer vacation, many European leaders suddenly rushed to Washington to support Zelenskyy. They must have finally decided to take action, sensing that ceasefire negotiations were now getting serious. This makes me think: “So typical of Europe. They are always slow in knowing what they are doing – just like us Japanese!”

Fourth, Steve Witcoff is an amateur. He is supposedly the Trump administration's special envoy to the Middle East, but in reality, he is a former New York real estate lawyer and nothing more than a golf buddy of Trump’s. Does he truly understand the meaning of “Article Five-like security guarantees as stipulated in the NATO Treaty”? The more I hear him speak about it, the more worried I become.

Fifth, Zelenskyy is not in the position to make critical choices on his own.

Given the characters involved in this game, it is nearly impossible to predict how much Zelenskyy can assert himself. The more details of the “agreement” between Putin and Trump become clear, the more difficult it will be for Zelenskyy to sell it to the Ukrainian people.

If things continue as they are, Trump's approach will be a typical “appeasement policy.”

Indeed, it is the same approach that British Prime Minister Chamberlain tried and failed at miserably before World War II. Therefore, even if a ceasefire is established, the outcome of this almost endless game will be as follows: Ukraine will lose some territory; it will not enjoy complete “security guarantees”; the possibility of direct U.S. involvement is low; Ukraine cannot be protected by limited guarantees from European countries alone; and, therefore, Russia will eventually resume military intervention somewhere in Europe.

I can only hope that my assessment is wrong.