President Trump has called the seizure of documents from his longtime personal lawyer Michael D. Cohen a “witch hunt” — and lawyers for both men were in federal court Friday seeking limits to what evidence federal prosecutors will get to see.

But Cohen has blurred the line between his personal dealings and work with Trump for nearly a decade, according to documents obtained through a freedom of information request into Cohen’s taxi medallions, the Forward has learned.

Cohen, who has worked for Trump since the mid-2000s and has been described as his “pit bull,” has used his Trump Organization email address to conduct business with New York’s Taxi and Limousine Commission since at least 2009. That could mean that if Cohen did anything illegal that involved both his taxi business and his work for Trump, it might be hard for either of them to maintain that Trump didn’t know anything about it.

The search warrant used by the FBI last week included a request for information about Cohen’s taxi medallion ownership, CNN reported.

Cohen’s usage of Trump Organization email was not just limited to taxi affairs: He also used his Trump account to negotiate a non-disclosure agreement with the porn actress known as Stormy Daniels in 2016, NBC reported in March.

“It exposes [Trump] to so many more risks,” David Shapiro, a former FBI legal adviser and expert in forensic accounting, told the Forward. “[Cohen has] now tied all of those things presumptively to the president, which is a world of hurt for [Trump] with the position he’s in.”

The raid on Cohen’s office, home and hotel room were in the spotlight Friday when Trump and Cohen, through their lawyers, asked a federal judge to keep the evidence under wraps until they can determine if they want to challenge the seizure on the grounds that the records are covered by attorney-client privilege.

Prosecutors said little if any of the evidence was likely covered by the privilege, and noted that the probe had been going on for months and focuses on Cohen’s business deals, not legal work.

U.S. District Judge Kimba Wood ordered Cohen to appear at a fresh hearing Monday and disclose a list of all his legal clients.

The possibility for legal exposure is one reason why lawyers are not supposed to mix their work on behalf of clients and other business dealings, Shapiro said. Indeed, the federal investigators who conducted the raid were looking in part for Cohen’s communications with a bank that loaned him money against his taxi business in 2014, according to The Washington Post.

The investigators were also looking for information about Daniels, whom Cohen paid $130,000 in 2016 to keep quiet about what she said was an affair with Trump. Cohen said Trump didn’t know about the payment.

The taxi-related emails would have been stored in Trump Organization servers for nearly a decade and should have raised red flags that he was conducting outside business through the company, Shapiro said. “[Trump] may be implicated in who knows what,” he added.

Investigators could use the emails as evidence to demand more communications from Cohen, which could in turn lead to more risk for Trump, said Fred Klein, a professor of law at Hofstra University who was a state and local prosecutor for more than 30 years.

In addition to the scrutiny over the Daniels payment, greater focus is being given to Cohen’s Russian connections, including negotiations about building a Trump Tower in Moscow, which included an email to President Vladimir Putin’s press secretary about getting the project approved.

Cohen has downplayed his Russian contacts, but several people who know him told the Forward that he has bragged about his connections to Russian businesspeople, including owning cabs in that country as well, according to multiple sources who declined to give their name out of fear of reprisals from the lawyer.

Cohen’s lawyer, Stephen Ryan, did not return an immediate request for comment.

Cohen owes more than $40,000 on more than a dozen taxi medallions, according to state records and information obtained through the FOIL request. He owns at least 32, according to the Daily News.

Medallions serve as licenses to pilot a yellow cab in New York. They can be bought and sold and owned by multiple people. The city of New York created the medallion program in 1937, when the number of taxis on the streets far exceeded the demand for cab rides.

The city has issued new medallions at a slow pace over the years; the current supply is capped at 13,587.

The low number of medallions put them in short supply and once caused their price to swell dramatically. Investors like Cohen saw a gold rush in yellow cabs and bought medallions by the handful, leasing them to drivers.

Prices peaked in 2014 at over $1 million. That year, the last medallion auction brought the city nearly $360 million in revenue from the sale of 350 new medallions.

Then Uber arrived on the scene. Ride-sharing services flooded the streets of New York with cheaper alternatives to taxis. As the number of cars offering ride sharing services in the city soared to 63,000 this year, the value of the medallion plummeted. In April, a medallion sold for $241,000, the lowest price this century.

That plunge means Cohen likely lost millions on his medallions. He also owns lucrative property investments, so it’s unclear if the crash in value is tied to his tax liabilities.

Ben Fractenberg is a reporter and photographer based in New York City.