Alexandra Lebenthal accuses Jimmy Cayne of manipulating her and of 'unconscionable actions' in loan lawsuit

Alexandra Lebenthal, president and CEO of Lebenthal & Co.
Adam Jeffery | CNBC

Just what, exactly, is Alexandra Lebenthal accusing Jimmy Cayne of?

An otherwise extremely dry legal filing by the Wall Street scion Lebenthal on Wednesday contains two eyebrow-raising claims against former Bear Stearns CEO Cayne.

Lebenthal, who Cayne is suing to recover more than $438,000 on an originally $1 million loan to her, alleges that Cayne "manipulated" her "in various ways."

It also alleged Cayne, 83, "engaged [in] conduct that has demonstrated unconscionable actions."

But Lebenthal's lawyers didn't elaborate on what they believe Cayne actually did in that filing, which asked a New York state judge to dismiss Cayne's suit.

Neither lawyers for the 53-year-old co-CEO of Lebenthal Holdings nor a lawyer for Cayne has responded to requests for comment by CNBC.

Lebenthal is a CNBC contributor.

Lebenthal's cryptic claims added another spicy ingredient to an already intriguing story involving two high-profile Wall Streeters who have seen their close friendship splinter over an amount of money they each would have consider pocket change at one time.

Lebenthal's grandparents started the municipal bond seller Lebenthal & Co., which was later run by her late father Jim — who made the firm well-known with his off-beat ads — and Alexandra herself.

Cayne sued Lebenthal last month in Manhattan Supreme Court, claiming that he had loaned her $1 million in 2008 when she approached him and said "she was struggling financially and asked to borrow money."

Cayne has said he gave her the cash as a personal loan "without hesitation and out of personal affection," less than a month before Bear Stearns collapsed.

Lebenthal made a series of payments on the loan in the following years.

But Cayne, in his lawsuit, says she "has not made a payment on the Loan since December 31, 2015."

"Now, in a dishonest attempt to avoid her obligation to plaintiff, defendant is attempting to force plaintiff to accept pennies on the dollar by incorrectly characterizing this personal debt as company debt," Cayne's lawsuit said.

The suit said that after Cayne's lawyer sent a demand to Lebenthal on January 5, 2017, that she immediately pay off the rest of the loan, Lebenthal's lawyer "indicated that she did not intend to pay the outstanding balance."

Lebenthal, in her answer to the lawsuit, which her lawyers filed Wednesday, admits that Cayne "made a loan."

But the filing goes on to say, among other things, that, "The Complaint must be dismissed because Plaintiff [Cayne] has intentionally manipulated Defendant in various ways in order to cause a circumstance that Plaintiff could subsequently allege to be adverse to his interest."

"In doing so, Plaintiff has breached his duty to act in good faith and to deal fair dealing with respect to his agreement with Defendant," Lebenthal's filing says.

The answer goes on to say that Cayne "has engaged [in] conduct that has demonstrated unconscionable actions, and therefore this matter must be dismissed."

On top of that, Lebenthal asked that after the case is dismissed that a judge award her "damages, applicable legal fees, costs and expenses."