The Senate Judiciary Committee will attempt during a closed-door hearing Wednesday to get to the bottom of the alleged “unmasking” of Trump campaign and transition officials by the Obama White House — furthering a potentially explosive counter-narrative coursing beneath the various congressional probes into alleged Russian meddling in the 2016 presidential election.

Former National Security Adviser Susan E. Rice, in addition to other top officials from the Obama administration, have come under suspicion during recent months amid accusations that they inappropriately “unmasked” requests to identify Trump associates caught up in clandestine surveillance of Russian operatives prior to and during the immediate aftermath of the November election.

While Republican lawmakers have during recent months led the charge for a deeper investigation into the unmasking allegations, it was a key Democrat on the Judiciary Committee who raised the issue during a public committee hearing on Tuesday, asserting that lawmakers hope to explore it more deeply with FBI officials during a secret hearing slated for Wednesday.

Sen. Sheldon Whitehouse, Rhode Island Democrat, warned the FBI’s National Security Branch Executive Assistant Director, Carl Ghattas, that he specifically wants answers during Wednesday’s closed-door hearing about President Trump’s former national security adviser, Michael Flynn, who resigned over contacts with Russia.

“There is a specific allegation that has been floating around that the conversations between Michael Flynn and [Russian] Ambassador Kislyak came into the White House with Flynn masked,” Mr. Whitehouse told his fellow committee members. “And that a decision was made in the Obama White House to unmask him — which then led to leaks to the newspapers, and so forth.”

Mr. Ghattas heads up the FBI’s operations and intelligence efforts involving all national security matters.

Mr. Whitehouse said the Senate needs a clear timeline of the facts, including whether Mr. Flynn, who met the Russian Ambassador after the Trump presidential victory, was masked or unmasked at the White House, information about the subsequent media leak, and whether or not there was a White House request for Mr. Flynn’s name to be un-redacted from the raw intel.

“I think we can all agree that the unmasking for a political purpose that leads to a leak is is not a good thing,” he said.

Information on the alleged ‘unmasking’ of Trump officials has been hard to come by.

Rep. Devin Nunes, California Republican and chairman of the House Permanent Select Committee on Intelligence, has been an outspoken proponent of focusing on the issue.

On May 31, Republicans and Democrats on the House intelligence committee issued a series of subpoenas related to the Russia investigations. Three of the subpoenas — sent to intelligence community agencies — sought records relating to alleged unmasking requests made by senior Obama administration figures, including Ms. Rice, CIA Director John O. Brennan and U.S. Ambassador to the U.N. Samantha Power.

In March, Ms. Rice admitted to requesting the unmasking of the names of some Americans redacted in raw intelligence reports on the U.S. surveillance intercepts, but argued that the requests were well within her job duties as national security adviser and were in no way driven by political motivations to know which figures from the Trump campaign were being discussed.

Earlier this month, Mr. Whitehouse also suggested that Mr. Flynn has made a deal with the FBI and will testify against Mr. Trump. While no statements have been made about cooperation, Mr. Whitehouse has said he’s “connected dots” to come to this conclusion.

“All the signals are suggesting [Mr. Flynn] is already cooperating with the FBI, and may have been for some time,” he told CNN.

“One of the most talkative people in Trumpland [Mr. Flynn] has gone absolutely silent,” he said. “That is exactly what a prosecutor would strongly encourage a cooperating witness to do … in order to avoid lengthy imprisonment.”

Mr. Whitehouse also pointed to moves that Mr. Flynn has made since his resignation — including cleaning up areas of noncompliance regarding his interaction with foreign governments — as further evidence the retired general is cooperating with federal agents in the Russia investigation.

• Alex Swoyer contributed to this story.

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