Steve Witkoff Is a Master of Confusion

I am not a foreign policy expert, but I have learned to recognize when someone is clearly out of his depth in that area. This is clearly the case of Steve Witkoff, a real estate investor and golfing buddy of President Donald Trump’s from his old stomping grounds in Queens, N.Y.

Witkoff, nominally the U.S. special envoy to the Middle East, has become Trump’s all-purpose emissary for almost all of today’s key foreign policy issues. One day he is meeting with Vladimir Putin to settle the Ukraine conflict, the next he is negotiating with Hamas to urge the group toward a cease-fire with Israel, and, a few days later, he is interacting with the Iranians on their nuclear weapons program. Witkoff’s travel schedule is often busier than that of a secretary of state or CIA director.

The jet-setting diplomat won Trump’s trust and backing by helping, in January, to bring home some Israeli hostages from Gaza as well as a U.S. citizen held by Russia. Not since Jared Kushner, the president’s son-in-law, who was ubiquitous during the first Trump term, has anyone in Trump’s circle been given so long a leash to negotiate on behalf of the U.S. Witkoff has walk-in privileges to the Oval Office, books himself for TV and podcast interviews, and works out of the West Wing rather than the State Department. “Marco Rubio may nominally be the Secretary of State, but it is Witkoff who is doing the shuttle diplomacy that has always gone with that role. And that is a disaster, because Witkoff is cluelessly — and dangerously — out of his depth,” concludes columnist Stephen Pollard of Britain’s Daily Telegraph.

Indeed, Witkoff so far has become known more for demonstrating confusion rather than his negotiating prowess. There’s no sign of a new truce in Gaza, Russia appears to be running out the clock in a diplomatic version of basketball’s four-corner stall, and neutral observers believe that the U.S. has been incoherent in its talks with the Iranians.

Consider just the most recent of Witkoff’s freelance gaffes: In an interview with Fox News Sunday last month, he admitted that he may have been “duped” by Hamas during the hostage negotiations. It’s one thing for negotiators to wing it during TV interviews, it’s another to imitate 1968 presidential candidate George Romney, who infamously admitted that he had been “brainwashed” by briefers over the Vietnam War.

Then, in an eyebrow-raising interview with Tucker Carlson, Witkoff said that he didn’t think Hamas is “ideologically intractable” and that it could be “involved politically” in Gaza if the terror group steps back from its military goals. He also appeared to take up Iranian talking points by saying he was seeking “a verification program” for its nuclear activity rather than the White House’s firm demand that the program must be “dismantled.”

In the same interview with Carlson, Witkoff wandered down a blind alley of favored Russian narratives regarding Ukraine. He called Putin “a super smart guy.” Moreover, he said, “I don’t regard Putin as a bad guy. . . . I liked him. . . . I thought he was straight-up with me.” Witkoff preposterously suggested that Russia doesn’t even want to control Ukraine: “Why would they want to absorb Ukraine?” As he mused on the possible shape of a peace deal between Russia and Ukraine, Witkoff floated the idea of formally handing over to Russia four Ukrainian regions — Luhansk, Donetsk, Zaporizhzhia, and Kherson — that Putin has already annexed: “There have been referendums where the overwhelming majority of the people have indicated that they want to be under Russian rule.”

“He apparently is unaware that those hastily called referendums under military rule were held after the conflict had caused anyone who opposed Putin to flee,” a top Russia analyst at the Pentagon told me. “No Western government has recognized them as valid.”

Many Trump supporters on Capitol Hill are concerned that Witkoff acts as if he has gone native. He recently invited Kirill Dmitriev, the Russian presidential envoy on foreign investment and economic cooperation, who was sanctioned by the U.S. following Russia’s invasion, to his personal residence for dinner. “U.S. officials shouldn’t host officials from adversaries with keen intelligence-gathering resources,” one administration official told me, noting that the dinner had to be moved to the White House on short notice.

When it comes to Ukraine, Witkoff’s actions are so shambolic as to remind one of just how much foreign policy chaos amateurs can create in their desire to please their patrons.

In 1938, for example, the Sudeten German minority in Czechoslovakia was agitating for union with Germany, at Hitler’s insistence. Britain was bound by treaty to aid the Czechs if Germany invaded, so it sent a special envoy to Prague to prepare a report. He was Lord Runciman, the son of a shipping magnate and former head of Britain’s Board of Trade. Runciman spent most of his weekend leisure time at the estates of the pro-German nobility, absorbing their grievances. He concluded that the demands of the Sudeten Germans were “in the main justified” and that the districts where they lived “should at once be transferred” to Nazi Germany. Nine days after Runciman’s report was published, Prime Minister Neville Chamberlain signed the infamous Munich Agreement, doing precisely that. Within six months, the rest of Czechoslovakia fell under German control.

No one is suggesting that a sellout on the scale of Munich is in the cards for Ukraine. I have long felt that a negotiated settlement would likely result in Russian troops’ occupying some Ukrainian soil. But it’s one thing to recognize reality and another to convince a wily adversary like Vladimir Putin, at the start of negotiations, that his talking points on Ukraine have found a willing transmission belt in Trump’s special envoy.

The best news on the Ukraine front may have come last Friday, when Secretary of State Marco Rubio warned that the U.S. would abandon talks if no clear sign of progress came within days. “We’re not going to continue with this endeavor for weeks and months on end,” Rubio noted, explaining that the U.S. had “other priorities to focus on.”

Perhaps one priority should be to direct special envoy Witkoff to less-treacherous diplomatic waters. I hear there is an ongoing debate at the State Department over whether the breakaway province of Somaliland, in the Horn of Africa, should be given formal diplomatic recognition by the U.S. Its key port city of Berbera is not Berlin, or even Baku, so there is little risk that Witkoff would be invited on U.S. news shows to opine on his diplomatic progress there.