One of the Trump administration’s first decisions about the fight against the Islamic State was made by Michael Flynn weeks before he was fired — and it conformed to the wishes of Turkey, whose interests, unbeknownst to anyone in Washington, he’d been paid more than $500,000 to represent.

The decision came 10 days before Donald Trump had been sworn in as president, in a conversation with President Barack Obama’s national security adviser, Susan Rice, who had explained the Pentagon’s plan to retake the Islamic State’s de facto capital of Raqqa with Syrian Kurdish forces the Pentagon considered the U.S.’s most effective military partners. Obama’s national security team had decided to ask for Trump’s sign-off, since the plan would all but certainly be executed after Trump had become president.

Flynn didn’t hesitate. According to timelines distributed by members of Congress in the weeks since, Flynn told Rice to hold off, a move that would delay the military operation for months.

If Flynn explained his answer, that’s not recorded, and it’s not known whether he consulted anyone else on the transition team before rendering his verdict. But his position was consistent with the wishes of Turkey, which had long opposed the United States partnering with the Kurdish forces — and which was his undeclared client.

Trump eventually would approve the Raqqa plan, but not until weeks after Flynn had been fired.

Now members of Congress, musing about the tangle of legal difficulties Flynn faces, cite that exchange with Rice as perhaps the most serious: acting on behalf of a foreign nation — from which he had received considerable cash — when making a military decision. Some members of Congress, in private conversations, have even used the word “treason” to describe Flynn’s intervention, though experts doubt his actions qualify.

But treason or not, Flynn’s rejection of a military operation that had been months in the making raises questions about what other key decisions he might have influenced during the slightly more than three weeks he was Trump’s national security adviser, and the months he was Trump’s primary campaign foreign policy adviser.

Even three months after he was fired, for lying to Vice President Mike Pence about a call with Russian Ambassador Sergey Kislyak, his role in the White House resonates.

With word that the president may have asked FBI Director James Comey to drop any criminal probe of Flynn — failure to register as a foreign agent is a federal crime — there is renewed focus on getting to the bottom of what Flynn did, and what Trump knew.

Despite the Trump administration’s attempts to downplay the red flags, it is becoming increasingly apparent that the administration was repeatedly warned about Flynn’s foreign involvement.

“This was a serious compromise situation that the Russians had real leverage,” former acting Attorney General Sally Yates said in an interview with CNN on Tuesday, after White House press secretary Sean Spicer downplayed her warning about Flynn’s interactions with Russian officials as just “a heads up.”

Flynn’s actions were also the subject of discussion just last week at a Senate Intelligence Committee hearing on national security threats, with Sen. Ron Wyden, D-Ore., zeroing in on the 18 days that passed between Yates’ warning that Flynn might be subject to Russian blackmail and Flynn’s forced resignation.

“Blackmail, by an influential military official, that has real ramifications for global threat,” he said. “So this is not about a policy implication, this is about the national security adviser being vulnerable to blackmail by the Russians.”

Flynn’s connections to Russia have been widely discussed. In 2015, he was paid more than $33,000 to speak at a gala dinner in Moscow where he was seated next to President Vladimir Putin. That alone may have exposed him to criminal charges: As a retired U.S. military officer, Flynn was required to seek permission to travel and to receive payment from a foreign entity, something the State Department and the Pentagon have told Congress he did not do.

But it is his paid work on Turkey’s behalf that offers the clearest evidence of his role as a foreign agent — and of his legal problems, since he did not declare his foreign agent status till weeks after he’d left the Trump administration.

It was a fact Flynn disclosed himself in a declaration to the Foreign Agent Registration Unit of the Justice Department in early March. According to Flynn’s paperwork, he was paid $530,000 for work that “could be construed to have principally benefited the Republic of Turkey.” The contract ended last November.

Under the Foreign Agent Registration Act, U.S. citizens who lobby on behalf of foreign governments or political entities must disclose their work to the Justice Department within 10 days.

Ekim Alptekin, the Turkish businessman whose company paid Flynn, disputes that he was “taking directions from anyone in the government” of Turkey. But Flynn’s filing shows he set up a meeting with Turkey’s foreign minister, Mevlut Cavusoglu, and energy minister, Berat Albayrak, who is President Recep Tayyip Erdogan’s son-in-law, at a New York hotel last September.

As then-candidate Trump’s national security adviser, Flynn sat in on classified briefings in the summer and fall of 2016. According to the filing, he signed the contract with Alptekin’s firm on Aug. 9. Trump received his first classified intelligence briefing on Aug. 18 — a meeting Flynn attended. As Trump’s national security adviser in the White House, Flynn had access to even more highly classified intelligence. He sat in on most, if not all, of Trump’s phone conversations and meetings with foreign leaders.

How much Trump knew about Flynn’s paid foreign-agent work is uncertain. When Flynn’s firm filed the Justice Department paperwork in March, the White House said Trump was unaware that Flynn had been paid to lobby on Turkey’s behalf. But Flynn’s lawyer has said he called Trump’s transition team before the inauguration, asking whether Flynn should register as a foreign agent.

When asked why the call had not been an obvious indication to act quickly, the White House tried to smooth it over by saying its legal counsel had considered it a private decision the transition team should not get involved in.

After Trump made Flynn his national security adviser, there were high hopes in Ankara that the new administration would give in to Turkey’s wishes “since many of Turkey’s views overlap with the incoming president,” in the words of an article in the Daily Sabah, a pro-government newspaper. In interviews with visiting foreign journalists in March, Turkish officials repeatedly expressed optimism about working with the Trump administration after years of withering relations with the Obama administration.

Turkey would finally have someone who listened to the two things they wanted: to nix any plans of working with the YPG once and for all, and to extradite Fethullah Gulen, a Turkish cleric living in exile in Pennsylvania. Erdogan’s government suspects Gulen and his followers of masterminding a failed coup attempt last July.

In another indication of the close ties between the new administration and Turkey under Flynn, the Turkish-U.S. Business Council’s annual summit, which is chaired by Alptekin, moved its meeting to the Trump International Hotel in Washington this year. The summit, which is in its 36th year, had in previous years been at the Ritz-Carlton. The new location was announced the day before Flynn was fired.

Treason is the only crime that is defined in the Constitution, where it’s described as levying war against the U.S. or “adhering to” an enemy — helping them, in other words. An enemy is a nation or organization against whom the U.S. has declared war, said Carlton Larson, a law professor at the University of California, Davis who specializes in treason.

While nonstate actors like ISIS probably fit the definition, Flynn’s action not to support a specific group against them does not legally fit the bill, Larson said. Even at the height of the Cold War, when Julius and Ethel Rosenberg handed over nuclear secrets to the Soviet Union, they were tried and executed not for treason but for espionage.

However, given Flynn’s many connections to Russia and Turkey, with documented payments, Democrats have dusted off a chain of little-known ways he could have violated the Constitution.

In February they asked the Pentagon to look into whether he had violated the Constitution’s emoluments clause by accepting money for his 2015 Moscow speaking engagement at a gala marking the 10th anniversary of the state-owned RT television channel. The clause prohibits former military officers from accepting gifts from foreign governments without the approval of Congress.

After he was fired, many Democrats also pointed to the Logan Act, an obscure 1799 statute that bars private citizens from interfering with diplomatic relations between the U.S. and foreign governments.

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(Matthew Schofield contributed to this report.)

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©2017 McClatchy Washington Bureau. Distributed by Tribune Content Agency, LLC.

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