A federal judge has ordered Michael Cohen, Trump’s longtime personal attorney and “fixer,” to turn over his list of clients by Monday at 10 a.m. The list, the judge says, will be made public.

For Cohen, this is a major problem.

The request comes after Cohen’s home, hotel room, and office were raided by F.B.I. agents on April 9. The raid came after the office of the U.S. Attorney for the Southern District of New York sought and obtained a search warrant. Prosecutors sought the warrant following a referral from Special Counsel Robert Mueller, who apparently uncovered information that he believed might be evidence of a crime.

The information seized reportedly relates to hush money payments made to Stormy Daniels and Karen McDougal, two women who allegedly had affairs with Donald Trump.

Cohen sought a temporary restraining order last week to prevent prosecutors from reviewing the information, claiming that it was covered by attorney-client privilege. The seized records “contain thousands if not millions of documents that are protected by attorney-client privilege,” Cohen’s attorney, Todd Harrison, told U.S. District Judge Kimba Woods.

Federal prosecutors, however, say this is all a ruse. They claim Cohen is “performing little to no legal work” and his only real client is Donald Trump, who doesn’t use email. As a result, prosecutors argue there is little to no privileged information in seized material.

In an effort to evaluate these competing narratives, Woods has ordered Cohen to turn over his client list to the court on Monday morning. Cohen was unable to tell the court how many clients he has on Friday because he didn’t bother to show up at court, opting instead to smoke cigars with his buddies.

Michael Cohen (C), U.S. President Donald Trump's personal attorney, chats with friends near the Loews Regency hotel on Park Ave on April 13, 2018 in New York City. CREDIT: Photo by Yana Paskova/Getty Images Michael Cohen skips court to smoke cigars, judge fumes

This is where things get very dicey for Cohen.

Although Cohen worked pretty much exclusively for Trump, he also appears to serve as a “fixer” for Trump’s friends and family. Cohen, it seems, has a specialty in covering up affairs.

It was revealed last week that Cohen recently helped Elliott Broidy, a major Trump fundraiser, negotiate a non-disclosure agreement with a Playboy Playmate he impregnated. (He reportedly charged Broidy $250,000 for this service.) Cohen also successfully killed an US Weekly story about an alleged affair between Donald Trump Jr. and singer Aubrey O’Day in 2013. (The story was reported after Trump filed for divorce last month.)

So Cohen could provide the court with an expansive list of everyone he assisted and claim they were his clients. This would maximize the chance that potentially damaging information will be withheld from prosecutors under attorney-client privilege. In so doing, however, he may subject many people to the assumption that they sought his help to cover up an affair or other misconduct.

Alternatively, Cohen could provide a very short list to the court. This would serve to protect the identities of people who sought his help to silence a woman or for other unappealing matter. But it would also all but ensure that more potentially incriminating materials makes it to federal prosecutors.

Cohen could also try to defy the court order and not turn over a list of his clients at all. Defying an order of a federal judge is not a particularly good option, however.

For years, Cohen has secretly done the dirty work for Donald Trump and his associates under the protective umbrella of “attorney-client privilege.” This isn’t really legal work but pretending it was helped ensure it stayed secret. The gig may be up.

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