Former Exxon Mobil CEO Rex Tillerson, Donald Trump’s nominee for secretary of state, is clearly an intelligent and well-informed man. During the first six hours or so of his confirmation hearing before the Senate Foreign Relations Committee on Wednesday, Tillerson was polished, articulate, and clearly knowledgeable about countries ranging from Saudi Arabia to North Korea to Equatorial Guinea.

The hearing went badly for him anyway.

There was one issue, above all others, that mattered in these hearings: Russia. Tillerson, the former head of Exxon’s division in that country, has more than a decade and a half of associations with Vladimir Putin personally, and his opposition to sanctions against Russia is a matter of public record. Republican committee members who are hawkish on Russia, most notably Marco Rubio, came into today’s hearing with serious reservations about Tillerson’s ties to the Kremlin. And without their votes, Tillerson faces a low chance of making it out.

Tillerson did a poor job of reassuring them. He refused to label Putin a “war criminal” when prompted to do so by Rubio, did nothing to clear up the nature of his personal relationship with Putin, refused to take a clear position on new Russia sanctions, and may have outright lied about his company lobbying against the current ones.

Part of the issue is that Tillerson’s (and Exxon’s) record on Russia record is, in fact, hard to defend to a Russia hawk. But the bigger problem is that Trump’s record on Russia is hard to defend.

Any pick for secretary of state would have been forced to toe his prospective boss’s weird, admiring line on the Kremlin — and would have been subject to withering questions as a result. The hearings highlight just how much Trump’s refusal to see Russia as an adversary isolates him from congressional Republicans, and how many problems it could create for his administration in the coming years.

And as for Tillerson personally, whether he makes it through is still very much an open question.

The hearing started badly on Russia

In his opening statement, Tillerson tried to appease the committee’s Russia hawks — arguing that the Obama administration had been too weak in responding to Russia’s invasion of Ukraine. But once questions began, Tillerson’s line on Russia started to change.

Rubio was one of the first senators to get to question Tillerson, and he went right for the jugular on Russia, asking Tillerson whether he’d support sanctions on any Russian officials involved in hacks on the United States.

“I would want to examine all the corners, all four corners of that,” Tillerson answered.

“Those are the four corners,” Rubio replied. “We would sanction people who are involved in cyberattacks against the United States and interfering in our elections.”

Tillerson still refused to provide a more concrete answer. A visibly irritated Rubio then read out a list of documented atrocities committed by Russian military forces, including intentionally bombing Syrian civilians in the city of Aleppo, and asked Tillerson if he considered them to be war crimes. Tillerson, once again, refused to answer definitively.

“You are ... not prepared to say that Vladimir Putin and his military have violated the rules of war and have conducted war crimes in Aleppo?” Rubio asked.

“Those are very serious charges to make,” Tillerson said, adding that he needed “to be fully informed” before making such a determination.

“There’s so much information out there. It should not be hard to say that Vladimir Putin’s military has conducted war crimes in Aleppo, because it is never acceptable to target civilians,” Rubio replied. “I find it discouraging, your inability to cite that.”

Then it got worse

After being dressed down by the most important vote on the committee — Rubio plus all the Democrats would be enough to block his confirmation — Tillerson jumped out of the frying pan and into the fire. When asked if he or Exxon Mobil had lobbied against Russia sanctions, he said no, categorically.

“I have never lobbied against sanctions,” Tillerson said. “To my knowledge, Exxon never directly lobbied against sanctions.”

This seems very hard to believe. As CEO, Tillerson spearheaded a series of deals in Russia valued at hundreds of millions of dollars — which means that sanctions against Russia could potentially have cost his company hundreds of millions of dollars. In June 2014, when Russia sanctions were being considered on Capitol Hill, Tillerson told reporters that his company was making its views about sanctions clear to the United States government. “Our views are being heard at the highest levels,” he said.

Tillerson’s dubious claim that neither he nor Exxon ever lobbied against sanctions began to unravel almost immediately. Sen. Bob Corker, the committee chair, pulled at the string: "I think you called me at the time,” he said, referring to when Russia sanctions were being debated on the Hill.

Ouch.

A bit later, after a short break, Corker gave Tillerson a chance to finesse his response. Tillerson argued that he and Exxon never lobbied against sanctions per se, but merely engaged with Congress to understand how Exxon’s business would be affected. “Exxon Mobil participated in understanding how the sanctions were going to be constructed,” he said.

As questioning went on, this claim became flimsier and flimsier. Sen. Bob Menendez cited four separate lobbying reports showing Exxon Mobil lobbying on sanction bills covering both Russia and Iran — lobbying reports that companies only file if they have engaged in actual lobbying, and not just the sort of basic information gathering that Tillerson was describing.

“Were we lobbying for the sanctions or against them?” Tillerson asked Menendez, somehow keeping a straight face.

“I know you weren’t lobbying for the sanctions,” Menendez replied. Tillerson had no real reply to this, and just kept deflecting until Menendez finally moved on.

This whole line of questioning was brutal, because it forced Tillerson to try to square a circle. In order to satisfy his questioners, he would have needed to show that he had supported sanctions against Russia. Otherwise, they would have a (reasonable) suspicion that as secretary of state, he might potentially try to undermine the sanctions regime against Russia, which they see as an essential bulwark against Russian expansionism and interference in the American political process.

But Tillerson has always opposed these sanctions, because he’s always thought about the world through the lens of what’s good for Exxon — as most CEOs would. And banning commerce with Russian oil giants is very, very bad for Exxon’s bottom line. So Tillerson took a wishy-washy line on current sanctions, saying, "I would recommend maintaining the status quo until we are able to engage with Russia and understand better what their intentions are.”

If he took a stronger pro-sanctions stance in the hearing, Tillerson would have contradicted himself and sold out his corporate buddies. If he outright opposed Russian sanctions, as he had in the past, then he would have given Rubio and Democrats every reason to spike his nomination.

He thus tried to avoid both pitfalls by simply giving vague, qualified answers and dissembling about Exxon’s record on sanctions. But no one was fooled, and he just ended up looking ridiculous.

The perils of being a Trump appointee

At around the same time Tillerson was being hammered by Rubio and Menendez, Trump was hosting his first press conference since being elected president. It centered, naturally, on recent unverified reports that Russia may have a blackmail file on the president-elect. Trump, naturally, denied all of the allegations and went on the offensive.

“If Putin likes Donald Trump, guess what, folks, that's called an asset, not a liability,” he said, referring to himself in the third person.

This has been Trump’s line for months — and needless to say, it is not a popular opinion on Capitol Hill. This puts Tillerson, a man who received the Order of Friendship medal from Putin in 2013 in recognition of oil partnerships, in yet another very awkward position. He either backs Trump’s praise for Putin, rendering himself radioactive as a candidate for secretary of state, or he contradicts his prospective boss — a dangerous move for any Trump employee.

So Tillerson, once again, backed away, demurring on repeated attempts to get him to comment on Trump’s Russia statements. At one point, Menendez asked him whether he had discussed Russia with Trump. “That has not occurred yet,” he said.

"That's pretty amazing,” Menendez replied.

Trump’s bizarrely friendly approach to Moscow would be a problem for anyone in Tillerson’s position. No nominee would be able to give a satisfactory answer to questions about sanctions, at least in public, without countermanding their boss. Tillerson’s background makes the problem particularly acute, as his record on Russia is objectively eyebrow-raising, but it’s not unique to him.

This shows one of the primary ways Trump has marginalized himself right from the get-go: By taking such outlandish positions on such an important issue as Russia — positions that directly contradict the view of the GOP establishment — he has set himself up for conflict after conflict with people who nominally ought to be his allies.

Whether it’s secretary of state hearings, a new Russia sanctions bill supported by some Republicans, or an inquiry into Russian hacking during the US election, Trump has tweeted and blustered his way into a presidential term that will almost certainly be defined by conflict over Russia. In that sense, then, the surprisingly brutal Tillerson hearing is a preview of what’s to come.

Will Tillerson be confirmed?

It’s hard to say what this conflict means for Tillerson’s confirmation. On the one hand, his performance was clearly not satisfying to a lot of senators. On the other hand, he reportedly did better on Russia in his private meetings with members of the committee.

But he doesn’t have a lot of room for error. Democrats are inclined to oppose his nomination, both because he’s a Trump appointee and because Exxon Mobil is one of the world’s biggest contributors to climate change. When Sen. Tim Kaine pressed Tillerson on Exxon’s long history of funding climate change deniers, Tillerson got downright defensive.

"Senator, since I’m no longer with Exxon Mobil, I’m in no position to speak on their behalf,” he said.

"Do you lack the knowledge to answer my question, or refuse to answer my question?" Kaine replied.

"A little of both,” Tillerson said.

The secretary of state should, in theory, have a great deal of influence over climate policy. Solving climate change requires international cooperation — big emitters like the US and China need to agree to move away from carbon together, or else the realities of international competition mean nobody probably will. The 2015 agreement struck in Paris is, for that reason, widely seen as one of the Obama administration’s most significant foreign policy achievements — it created a framework for that kind of crucial cooperation down the line.

Trump has said he wants to pull the US out of the Paris agreement, which would effectively scuttle it. Tillerson, given his position, could very well help shape how Trump acts on this idea, or whether he does anything at all. Given the stakes — human civilization — the Democrats on the Foreign Relations Committee seemed understandably nervous about entrusting this critical position to a former oil executive.

If Democrats decide to take a consistent party line against Tillerson, due to his position on climate, then he needs near-total Republican support. And if Rubio’s harsh questioning on Russia is any indication of party sentiment, he may not get it. After the hearing, Rubio told reporters that he was “prepared to do what's right” — meaning he might well vote against Tillerson’s confirmation.

Now, none of this may come to pass. Democrats may decide this is about as good as they’re going to get with Trump, and Republicans might decide to back their president.

But they also might not. And given this uncertainty, Tillerson can’t be very happy about his dismal performance today.