Before he started showing up on TV at all hours defending Donald Trump, New York City lawyer Joseph Tacopina faced two bitter lawsuits — one from disgraced former New York City police commissioner Bernard Kerik — accusing him of unethical behavior and malpractice.

An attorney who hired Tacopina to bring a potential lawsuit against her Connecticut law firm discovered he had negotiated to be hired by that same firm as “co-counsel” — while purporting to represent her interests.

And after Tacopina represented Kerik in a state fraud case, Kerik accused him of disclosing privileged communications to federal prosecutors in a separate tax evasion case brought against the one-time top cop to which he ultimately pleaded guilty.

Kerik even claimed Tacopina had tried to cheat him out of his fair share of a finder’s fee in a real estate deal.

Since word of Trump’s expected indictment surfaced in The New York Times last week, Tacopina has been a regular presence on TV, insisting the former president broke no laws regarding an alleged $130,000 payment on the eve of the 2016 election to a former porn star over her allegations of a brief affair with him.

In multiple TV appearances, Tacopina has defended Trump with a combination of mockery and barely suppressed outrage. He has claimed the payment to Stormy Daniels — which former Trump fixer Michael Cohen says was improperly disguised as “legal work” — was just part of a “completely legal settlement agreement.” Tacopina has vowed to challenge “every potential issue,” has dubbed the expected indictment “political persecution” and asserted that “the rule of law died in this country” the day word emerged of the pending charges.

The well-dressed, pugilistic lawyer is a longtime fixture in New York City’s tabloid coverage of crime and justice, where attorneys are sometimes dubbed “mouthpieces” and hyperbole is often the coin of the realm. A former Brooklyn prosecutor and criminal defense attorney, Tacopina has spent a fair amount of time in the headlines representing high-profile clients such as Alex Rodriguez (appealing a Major League Baseball doping suspension) and Meek Mill (overturning a gun and drug case against the rapper).

But as part of a legal lineup representing Trump, along with seasoned New York City criminal defense lawyer Susan Necheles and former federal prosecutor Todd Blanche, Tacopina has hit new heights of public recognition.

Meanwhile, sitting in dusty court files are accusations and allegations that paint a much darker portrait of Tacopina, starting with a case filed anonymously by an associate at a Connecticut law firm who alleges she was pressured into having sex with one of that firm’s partners.

The associate — listed as “Jane Doe” — hired Tacopina in 2010 after realizing she had contracted a sexually transmitted disease following the affair with the partner, according to court papers. She turned to Tacopina at the recommendation of another lawyer they both knew, and he agreed to take her case.

The case was settled in 2011 for $750,000, of which $200,000 went to Tacopina. The associate left the firm, but the associate soon learned that Tacopina had a unique relationship with her former employer.

Less than two weeks after the settlement was signed, while Jane Doe was still awaiting payment and Tacopina was still representing her, an email filed in court from Tacopina reveals he suggested the Connecticut firm partner with him as “co-counsel” on pending litigation he was planning to file in that state. At the time, Tacopina did not have a license to practice law in Connecticut state courts, he acknowledged in legal filings.

Tacopina continued representing Jane Doe through mid-January 2012, while also serving as co-counsel to the firm she had hired him to potentially sue. The associate says she did not learn of this co-counsel deal until 2013, and she filed suit against Tacopina alleging legal malpractice and breach of contract in 2014.

Jane Doe’s lawsuit alleged that “the agreement between Tacopina and the Connecticut firm existed at the time of his representation of the plaintiff. At no time did Tacopina or anyone at the firm inform Plaintiff of Tacopina’s association with the Connecticut firm.”

Manhattan Supreme Court Justice Joan Kennedy dismissed the malpractice claim due to statute of limitation restrictions, but ruled the breach of contract accusation could go to trial. Kennedy also dismissed Tacopina’s defamation counterclaim against Jane Doe.

In mid-2017 Jane Doe’s case was discontinued with an undisclosed settlement. Neither Tacopina nor Jane Doe’s attorney, Matthew Schwartz, responded to THE CITY’s questions about the case.

Shunned By the Mob

A similar response came from another, much more well-known former client of Tacopina’s: ex-NYPD commissioner Kerik, who pleaded guilty to eight felony charges in 2009 and served time in federal prison.

Kerik — who was ultimately pardoned by Trump — has long been one of the ex-president’s staunchest allies and continues to toe the line. “I am here to support the President,” he said on Friday.

But don’t ask him about Tacopina, the showy lawyer who once stood by Kerik’s side as he faced a precipitous fall from grace. There is no love lost between them.

“I am not going to get into it,” the normally loquacious ex-cop said when asked by THE CITY about Tacopina.

Tacopina represented Kerik when the ex-top cop pleaded guilty in 2006 to accepting thousands of dollars in unreported gifts and a loan from people doing business with the city. The plea deal was a good one: Kerik admitted only to misdemeanors, agreeing to pay $221,000 in fines, with no jail time.

Within a few years, however, Kerik was asking the state disciplinary committee to disbar Tacopina, whom he accused of secretly cooperating against him as a witness in a federal investigation that resulted in a 48-month prison sentence for Kerik for tax fraud.

Kerik then in 2014 filed a civil racketeering case against the lawyer in federal court, alleging 11 separate predicate acts. He urged the feds to charge Tacopina with perjury and also alleged that his former lawyer tried to cheat him out of his fair share of a finder’s fee in a real estate deal worth $2.5 million.

Tacopina did not respond to questions emailed by THE CITY.

In his fight with Kerik, Tacopina was represented by attorney Lanny Davis. Now they’ll square off against each other. Davis is representing former Trump attorney Cohen, who served prison time in connection with his role in providing hush money to Daniels and is likely to be the star witness against Trump. He did not respond to requests for comment about his former client.

The federal lawsuit was dismissed in 2014, but for Kerik the anger still simmers. 

“I am not going to get into it,” Kerik said repeatedly when asked about his former attorney and his past accusations.

Had his friend, the former president, consulted him about hiring Tacopina? “Nobody asked me,” he said. “You know I am supporting the president whatever the decision is.”

Tacopina has long denied most of Kerik’s allegations against him, insisting that he was never going to be a witness against his former client in the federal case. But the allegation that he had cooperated with law enforcement appears to have cost him other potential clients, including those accused of being involved with organized crime.

“There were reports he had been too cozy with law enforcement,” said Gerald McMahon, a veteran criminal defense attorney who often represents defendants in mob cases. “Whether true or not, organized crime guys won’t have anything to do with him.”

Murray Richman, another veteran with many clients accused of having mob ties, said that any past taint won’t matter with Tacopina’s most famous current client. “They are made for each other,” said Richman. “Joe wants the attention and Trump will give him all the attention he wants.”