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President Donald Trump hands his pen to Isaac Perlmutter after signing an Executive Order on whistleblower protection in April.Andrew Harnik/The Associated Press

A defamation lawsuit involving a wealthy Toronto businessman and the billionaire chairman of Marvel Entertainment has taken a bizarre new twist with allegations of a big-money shakedown that involves Donald Trump's lawyer, Marc Kasowitz.

For years, Harold Peerenboom, founder of the multinational executive search firm Mandrake Management, has been locked in a bitter legal battle with his Palm Beach neighbour, Isaac Perlmutter, the notoriously reclusive head of the superhero media empire.

What started as a fight over management of a tennis court in their exclusive housing complex has devolved into a multimillion-dollar lawsuit over an alleged international smear campaign.

Recent court filings have added more wrinkles to an already complicated case. They call into question Mr. Peerenboom's long-held assertion that Mr. Perlmutter and his wife, Laura, were behind hundreds of pieces of hate mail about him sent to his neighbours, associates and even strangers starting in 2011.

Now, Mr. Perlmutter has accused Mr. Peerenboom of trying to frame him, suggesting in legal submissions that the Toronto businessman cooked up the defamation campaign with one of his former employees, and that his lawyer, Mr. Kasowitz, was in on the "extortion scheme."

Mr. Peerenboom, in his own new filings, maintains that he is a victim and points the finger back at the comic book billionaire.

Both men are members of Mr. Trump's Mar-a-Lago country club in Palm Beach, and Mr. Perlmutter considers the President a close friend. Mr. Kasowitz is also Mr. Trump's lawyer for the Russia investigation.

The new allegations stem from the discovery of a package sent from Toronto and intercepted at the border. It included letters discrediting Mr. Peerenboom. Toronto police have charged one of his former employees in relation to the parcel. In legal filings, Mr. Perlmutter says it proves he was never behind the smear job – and that the Toronto businessman and his legal team knew it all along.

Miami lawyer Roy Black, who represents Mr. Perlmutter, outlined the latest development in court documents filed on May 30, saying U.S. Customs and Border Protection agents had intercepted a "hate mail kit" that was being sent via UPS from Toronto to Florida in January, 2016.

The package consisted of sealed envelopes with preprinted addresses, latex gloves and four hate letters including one that falsely accused Mr. Pereenboom of being a child molester.

Officials sent a decoy box to a Flordia UPS facility, but no one picked it up.

But according to the Black filing, U.S. Homeland Security and Canadian authorities discovered it was mailed by former Mandrake employee David Smith, using an alias.

"David Smith is a former employee of Peerenboom's company, Mandrake, where he worked for 14 years, eventually rising to the rank of partner, and served as a director of a Mandrake affiliate," the court filing states. "David Smith's efforts were so clumsy they could only possibly fool someone – like Peerenboom – who either wanted to be fooled or was in on the act."

Mr. Smith was arrested and charged in Toronto on June 22 with forgery and criminal harassment and released on bail. As part of the bail conditions, he is not allowed to contact Mr. Peerenboom or Mr. Perlmutter.

Mr. Smith's lawyer, Frank Addario, had no comment when contacted by The Globe and Mail on Thursday.

Mr. Black claims in the court documents that Mr. Kasowitz may have known that "David Smith was responsible for the hate-mail campaign from the start" and kept the information secret.

"After throwing their lot in with Peerenboom and his criminal plot, Kasowitz has been forced to spin a web of lies, distortions, and misrepresentations to advance the extortion scheme and to conceal its fraudulent and illegal components," Mr. Black said in his filing.

Mr. Kasowitz and New York City colleague Michael Bowen filed a response calling the allegations "wholly irresponsible, and baseless." They described Mr. Smith as a disgruntled former employee who was fired in 2011 after being caught "misappropriating Mandrake proprietary information and other misconduct at the firm."

Their filing suggested Mr. Smith might be linked to Mr. Perlmutter.

"What is still unknown is what connection the Perlmutters themselves had with David Smith … or even the source of the tip that led to that border inspection," they said.

The Kasowitz legal team says Mr. Smith's alleged role in the hate-mail campaign was leaked to the Hollywood Reporter "to distract attention" from the court-ordered release of e-mails that show Mr. Perlmutter and an assistant had sent negative newspaper articles about their client to residents of the gated condominium complex in June, 2011.

Mr. Perlmutter has always denied he was involved in attempts to smear Mr. Peerenboom.

"For years, they lied about their involvement in the anonymous hate mail, tried to hide documents and inculpating emails and tried to cover it up through false legal filings, coercing and intimidating witnesses and suborning perjury," the Kasowitz-Bowen filing said.

Mr. Peerenboom's lawyers dismissed as "lunacy" and "moronic" the suggestion that the Canadian tycoon would subject himself to the "most vile slander – including claims of child molestation and murder" and incur massive legal bills "simply to try to shake down the Perlmutters."

They assert in the court document that Mr. Black made the allegations of a criminal extortion scheme in an attempt to prevent Laura Perlmutter from having to testify in the hate-mail case. She is scheduled to give evidence in early August. DNA evidence collected from one of the earlier hate letters allegedly matches DNA on a water bottle that Ms. Perlmutter left in court in a separate case on Feb. 27, 2013.

The Kasowitz filing also calls for sanctions against Mr. Black's firm for impugning the integrity of Mr. Kasowitz, who "is at the pinnacle of his career … which now includes having been selected to serve as personal counsel to the U.S. President in a matter of international import."

In a response on June 21, Mr. Black said the newspaper clippings that his client disseminated were not defamatory, and insisted the Marvel executive had nothing do with the hate letters that accuse Mr. Pereenboom of being a Nazi, child predator and murderer.

He did not retract the allegations of a criminal conspiracy.

At the centre of the legal soap opera is Karen Donnelly, the tennis instructor at the ritzy Palm Beach complex where the two men reside.

It is alleged that the 74-year old Mr. Perlmutter, an avid tennis player, was infuriated when Mr. Peerenboom wanted to hold a competitive bid for the position in 2011.

Soon after, the hate letter campaign began. The first letters were Canadian newspaper articles about Mr. Peerenboom's past legal entanglements in Canada and escalated in December, 2012, to accusations that he was a murderer and pedophile.

Both sides in the ongoing legal saga have hired private detectives and public relations experts.

Mr. Perenboom's lawyers have even launched a separate court case in New York City. Mr. Kasowitz subpoenaed further e-mail records from Marvel Entertainment in an attempt to prove that Mr. Perlmutter – one of the largest shareholders in Disney – started the hate campaign to force his client out of the swanky Palm Beach complex.

A New York judge is now examining 600 Marvel e-mails to determine whether they should be released to Mr. Kasowitz.

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